Silane-containing indolocarbazole compound and organic electroluminescent device thereof

Abstract

The application provides a silane-containing indolocarbazole compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The silane-containing indolocarbazole compound of formula 1 has good film-forming property, good stability, high carrier mobility and high triplet energy level, can effectively confine the carrier in a light-emitting layer to make the carrier combine to form an exciton and emit light, thereby improving the performance of the device, and remarkably improving the driving voltage, light-emitting efficiency, service life and the like of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent material, in particular to a silane-containing indolocarbazole compound and an organic electroluminescent device thereof. BACKGROUND

[0002] Electroluminescent materials can be divided into inorganic electroluminescent materials and organic electroluminescent materials. In the early stage, inorganic electroluminescent materials developed rapidly, while in the past two decades, organic electroluminescent materials have made great progress. Organic electroluminescent materials have more advantages than inorganic electroluminescent materials, mainly including diversification of preparation process, wide selection of materials and compatibility with large-area production and preparation process. Therefore, organic electroluminescent devices based on organic electroluminescent materials have very broad application prospects in the fields of flat panel display and solid-state lighting.

[0003] The light-emitting principle of an organic electroluminescent device is that, by applying a direct current to the cathode and anode, electrons and holes are injected into the device from the cathode and anode, respectively, under the action of an electric field, the carriers migrate in the auxiliary transport material, meet in the light-emitting layer to form excitons, and the excitons radiate back to the ground state and emit light.

[0004] The light-emitting layer of the device generally adopts a host-guest structure, and the host material is also an important component in the structure of the electroluminescent device. Electrons and holes migrating from the carrier transport layer are first captured by the host molecules, migrate to the LUMO and HOMO energy levels, respectively, and then recombine to form excitons. In order to achieve high energy utilization rate of the host-guest light-emitting device, on the one hand, the host must fully utilize the carriers to form excitons efficiently, and on the other hand, the exciton energy must be efficiently transferred to the light-emitting body to improve the utilization efficiency of the carriers.

[0005] Therefore, how to select a suitable host material to improve the light-emitting efficiency of the organic electroluminescent device and prolong the service life of the device is a problem worth considering. SUMMARY

[0006] In view of the problems in the prior art, the present application provides a silane-containing indolocarbazole compound and an organic electroluminescent device thereof.

[0007] The present application provides a silane-containing indolocarbazole compound, which is represented by the following formula 1,

[0008]

[0009] wherein one of X1 and X2 is a single bond, and the other is N (— L2— Ar2) ;

[0010] Ar1, Ar2are independently selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C6-C60 aryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C2-C60 heteroaryl, and at least one is selected from the group represented by Formula 1-a;

[0011] X3is selected from O, S, N(R0), C(R0)2, or Si(R0)2, R0, the same or different, is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C6-C60 aryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C2-C60 heteroaryl, or adjacent two R0s are bonded to each other to form a substituted or unsubstituted ring, but the two R0s do not form adamantane; or R0may represent a bond;

[0012] L, L1, L2are independently selected from one or a combination of a single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted 7-60 membered heteroarylene, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C6-C60 aryl, substituted or unsubstituted fused ring group of C3-C30 alicyclyl and C2-C60 heteroaryl;

[0013] Z, the same or different, is selected from C(Rz) or N, when Z is connected to X1or X2, it is selected from C; E, the same or different, is selected from C(Re) or N;

[0014] Rz, Re are independently selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring, or adjacent two Rz, adjacent two Re are bonded to each other to form a substituted or unsubstituted ring; in the case of Rz and Re being two or more, each of the Rz and Re is the same or different;

[0015] at least one of Ar1, Ar2, L1, L2, and Rz contains a group represented by formula 1-b;

[0016] R a, R b, R c are independently selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted C3-C30 cycloalkyl, or adjacent two groups are bonded to each other to form a substituted or unsubstituted ring;

[0017] However, the silane-containing indolocarbazole compound of formula 1 excludes structures represented by formula 1-b1 and formula 1-b2,

[0018]

[0019] In addition, the present application also provides an organic electroluminescent device containing the silane-containing indolocarbazole compound of the present application.

[0020] Beneficial effects: The silane-containing indolocarbazole compound of formula 1 of the present application has good film-forming property, good stability, high carrier mobility, and high triplet energy level, can effectively confine the carrier in the light-emitting layer to form excitons and emit light, thereby improving the performance of the device, and the driving voltage, luminous efficiency, service life, etc. of the device are significantly improved. DETAILED DESCRIPTION

[0021] The present application will be further illustrated below in conjunction with specific examples, which should be understood as merely illustrating the present application and not limiting the scope of the present application. After reading the present application, those skilled in the art can make various equivalent modifications to the present application, which all fall within the scope of the present application.

[0022] In the compounds of the present specification, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance. In the present application, "H", "hydrogen", "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, tritium.

[0023] In the present specification, the halogen includes fluorine, chlorine, bromine, iodine.

[0024] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional sites of the ring. For example, may mean and so on.

[0025] In the present specification, "adjacent two groups are bonded to form a ring" means that they are bound to each other through adjacent groups and are optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring can be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring can be a single ring or a polycyclic group. In addition, the ring formed by the binding of adjacent groups can be connected to another ring to form a spiro structure. As an example, the following is shown:

[0026]

[0027] In the present specification, the ring formed by the connection can be an aromatic ring or a non-aromatic ring, and can be a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, a fused ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but is not limited thereto.

[0028] In the present specification, the "integer selected from 0 to M" means that the value is selected from any one of the integers from 0 to M, including 0, 1, 2,..., M-2, M-1, M. For example, "n1 is an integer selected from 0 to 3" means that n1 is selected from 0, 1, 2, or 3. The same applies to the following.

[0029] In the present specification, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of "ZZ group" is not replaced by a substituent. For example, "unsubstituted aryl group" in "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of "aryl group" is not replaced by a substituent. The same applies to the following.

[0030] In the present specification, "CXX-CYY" in "a substituted or unsubstituted CXX-CYY group" represents the number of carbon atoms in the "group" which is not substituted, and when the "group" has a substituent, the number of carbon atoms does not include the number of carbon atoms in the substituent. For example, "C6-C60" in "a substituted or unsubstituted C6-C60 aryl group" represents the number of carbon atoms in the "aryl group" which is not substituted, and when the "aryl group" has a substituent, the number of carbon atoms does not include the number of carbon atoms in the substituent. The same applies to the following.

[0031] In the present specification, "substitution" in the "substituted or unsubstituted" means that at least one hydrogen atom in a group is replaced with a substituent. When a plurality of hydrogens is replaced with a plurality of substituents, the plurality of substituents can be the same or different. The position of the hydrogen replaced with the substituent can be any position. The substituent represented by "substitution" in the "substituted or unsubstituted" includes the following groups: deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted C3-C15 heterocyclic group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C15 alicyclic ring and a C6-C20 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C15 alicyclic ring and a C2-C20 heteroaromatic ring, and the like. Preferably, the following groups: deuterium, tritium, a cyano group, a halogen, a nitro group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a camphane group, a fenchane group, a trimethylsilyl group, a triethylsilyl group, a tripropylsilyl group, a triisopropylsilyl group, a tri-t-butylsilyl group, a triphenylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a chrysenyl group, a benzocyclopropane group, a benzocyclobutane group, a dihydroindenyl group, a tetrahydronaphthyl group, a benzocycloheptane group, a benzocyclobutene group, an indenyl group, a dihydronaphthyl group, a fluorenyl group, a benzofluorenyl group, a spirobifluorenyl group, a benzospirobifluorenyl group, a benzofuranyl group, a dibenzofuranyl group, a benzo-dibenzofuranyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzo-dibenzofuranyl group, an indolyl group, a carbazolyl group, a benzocarbazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, a quinoxalyl group, and the like. In addition, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring. In the present specification, "substitution" in the "substituted or unsubstituted" means that at least one hydrogen atom in a group is replaced with a substituent. When a plurality of hydrogens is replaced with a plurality of substituents, the plurality of substituents can be the same or different. The position of the hydrogen replaced with the substituent can be any position. The substituent represented by "substitution" in the "substituted or unsubstituted" includes the following groups: deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted C3-C15 heterocyclic group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C2-C20 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C15 alicyclic ring and a C6-C20 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C15 alicyclic ring and a C2-C20 heteroaromatic ring, and the like. Preferably, the following groups: deuterium, tritium, a cyano group, a halogen, a nitro group, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a camphane group, a fenchane group, a trimethylsilyl group, a triethylsilyl group, a tripropylsilyl group, a triisopropylsilyl group, a tri-t-butylsilyl group, a triphenylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a chrysenyl group, a benzocyclopropane group, a benzocyclobutane group, a dihydroindenyl group, a tetrahydronaphthyl group, a benzocycloheptane group, a benzocyclobutene group, an indenyl group, a dihydronaphthyl group, a fluorenyl group, a benzofluorenyl group, a spirobifluorenyl group, a benzospirobifluorenyl group, a benzofuranyl group, a dibenzofuranyl group, a benzo-dibenzofuranyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzo-dibenzofuranyl group, an indolyl group, a carbazolyl group, a benzocarbazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, a quinoxalyl group, and the like. In addition, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring.

[0032] In the present specification, the "substituted or unsubstituted silyl group" means a — Si(R k )3 group, wherein each R kthe same or different groups selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C60 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring. Preferably, each R k the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R k the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R

[0033] In the present specification, the alkyl group refers to a hydrocarbon group in which one hydrogen atom of an alkane molecule is removed, and the alkyl group includes straight-chain alkyl groups and branched-chain alkyl groups. A chain alkyl group having three or more carbon atoms includes isomers thereof, such as propyl groups including n-propyl, isopropyl, butyl groups including n-butyl, sec-butyl, isobutyl, and t-butyl, and the like. Examples of the alkyl group can include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and the like, but are not limited thereto. The number of carbon atoms of the alkyl group is 1 to 30, preferably 1 to 20, preferably 1 to 15, and more preferably 1 to 10.

[0034] In the present specification, the cycloalkyl group refers to a hydrocarbon group in which one hydrogen atom of a cycloalkane molecule is removed, and the cycloalkyl group includes monocyclic cycloalkyl groups, polycyclic cycloalkyl groups, and bridged cycloalkyl groups. Examples of the cycloalkyl group can include adamantyl, norbornyl, camphanyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. The number of carbon atoms of the cycloalkyl group is 3 to 30, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10.

[0035] In the present specification, the aryl group refers to a general term of a monovalent group obtained by removing one hydrogen atom from an aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a fused ring aryl group, or a combination thereof. Examples of the aryl group can include a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, a fluorenyl group, a benzofluorenyl group, a spirobifluorenyl group, a benzospibfluorenyl group, a spiroanthrafluorenyl group, and the like, but are not limited thereto. The number of carbon atoms of the aryl group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

[0036] In the present specification, the heteroaryl group refers to a general term of a group obtained by replacing one or more carbon atoms in an aryl group with a heteroatom, including an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorus atom, a boron atom, a silicon atom, and the like, but is not limited thereto. The heteroaryl group includes a monocyclic heteroaryl group, a fused ring heteroaryl group, or a combination thereof. Examples of the heteroaryl group can include a benzofuranyl group, a dibenzofuranyl group, a benzo-dibenzofuranyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzo-dibenzothiophenyl group, a carbazolyl group, a benzocarbazolyl group, a silafluorenyl group, a benzosilafuorenyl group, a spirofluorenoxanthrenyl group, a spirofluorenothioxanthrenyl group, a spirofluorenonitroanthrenyl group, a spirofluorenosilanoanthrenyl group, a benzodioxolyl group, a benzodithiophenyl group, a dihydroisobenzofuranyl group, a dihydrobenzofuranyl group, a dihydrobenzothiophenyl group, a dihydroisobenzothiophenyl group, a benzodioxinyl group, a dihydroacridinyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a quinoxalinyl group, and the like, but are not limited thereto. The number of carbon atoms of the heteroaryl group can be 2 to 60, preferably 2 to 30, preferably 2 to 25, and more preferably 3 to 18.

[0037] In the present specification, the fused ring group of an alicyclic and aromatic ring refers to a general term of a monovalent group obtained by removing one hydrogen atom from a fused ring of an alicyclic and aromatic ring. Examples of the fused ring group of an alicyclic and aromatic ring can include a dihydroindenyl group, an indenyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a benzocyclopropanyl group, a benzocyclobutanyl group, a benzocyclobutenyl group, a benzocycloheptanyl group, a benzocycloheptenyl group, and the like, but are not limited thereto. The number of carbon atoms of the alicyclic ring is 3 to 30, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10. The number of carbon atoms of the aromatic ring is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12, and even more preferably 6 to 10.

[0038] ​In the present specification, the fused ring group of the alicyclic and heteroaromatic ring refers to a total of the one valence group remaining after the alicyclic and heteroaromatic rings are fused together and one hydrogen atom is removed. Examples of the fused ring group of the alicyclic and aromatic ring can include pyridocyclopentane group, pyridocyclohexane group, pyridocyclobutane group, and the like, but are not limited thereto. The alicyclic ring has 3 to 30, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10 carbon atoms. The heteroaromatic ring has 2 to 60, preferably 2 to 30, preferably 2 to 25, preferably 2 to 18, and preferably 2 to 10 carbon atoms.

[0039] In the present specification, the arylene group refers to a total of the one valence group remaining after one hydrogen atom is removed from the aromatic nucleus carbon of the aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a fused ring arylene group, or a combination thereof. Examples of the arylene group can include phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, fluorenylene, benzofluorenylene, spirobifluorenylene, benzospirobifluorenylene, and the like, but are not limited thereto. The arylene group has 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 10 carbon atoms.

[0040] In the present specification, the heteroarylene group refers to a divalent group in which at least one carbon atom of the arylene group is substituted with a heteroatom. The heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, and the like, but is not limited thereto. The heteroarylene group includes a monocyclic heteroarylene group, a polycyclic heteroarylene group, a fused ring heteroarylene group, or a combination thereof. Examples of the heteroarylene group can include pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, naphthrylene, and the like, but are not limited thereto. The heteroarylene group has 2 to 60, preferably 2 to 30, preferably 2 to 25, and more preferably 3 to 18 carbon atoms.

[0041] In the present specification, the alicyclic and aromatic ring-based fused ring group refers to a total of the two valence group remaining after the alicyclic and aromatic rings are fused together and two hydrogen atoms are removed. Examples of the alicyclic and aromatic ring-based fused ring group can include dihydroindenylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocyclopropanylene, benzocyclobutylene, benzocycloheptylene, benzocyclobutenylene, naphthocyclopentylene, and the like, but are not limited thereto. The alicyclic ring has 3 to 30, preferably 3 to 25, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10 carbon atoms. The aromatic ring has 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, preferably 6 to 12, and more preferably 6 to 10 carbon atoms.

[0042] In the present specification, the alicyclic and heteroaromatic sub-fused ring group refers to a total of divalent groups remaining after removing two hydrogen atoms from an alicyclic and heteroaromatic ring fused together. Examples of the alicyclic and heteroaromatic sub-fused ring group can include pyridocyclopentane group, pyridocyclohexane group, pyridocyclobutane group, pyridocyclopentene group, and the like, but are not limited thereto. The number of carbon atoms of the alicyclic group is 3 to 30, preferably 3 to 20, more preferably 3 to 15, and even more preferably 3 to 10. The number of carbon atoms of the heteroaromatic group is 2 to 60, preferably 2 to 30, more preferably 2 to 25, even more preferably 2 to 18, and still more preferably 2 to 10.

[0043] In the present specification, "at least one" includes one, two, three, four, five, six, seven, eight, or more.

[0044] In the present specification, "at least one of each of Rz, R0, R1, Re, Rm, R2, Ry, Ry1, R3, and Rt" means at least one of a plurality of Rz, a plurality of R0, a plurality of R1, a plurality of Re, a plurality of Rm, a plurality of R2, a plurality of Ry, a plurality of Ry1, a plurality of R3, and a plurality of Rt. The same applies to the following.

[0045] The present application provides a silane-containing indolocarbazole compound represented by the following Formula 1,

[0046]

[0047] wherein one of X1and X2is a single bond, and the other is N(—L2—Ar2);

[0048] Ar1and Ar2are independently selected from one or a combination of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C30 alicyclic ring and a C6-C60 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C30 alicyclic ring and a C2-C60 heteroaromatic ring, and at least one thereof is selected from a group represented by Formula 1-a;

[0049] X3is selected from O, S, N(R0), C(R0)2, or Si(R0)2, R0, which is the same or different, is selected from one of or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C60 aryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C2-C60 heteroaryl, or adjacent two R0s are linked to each other to form a substituted or unsubstituted ring, except that two R0s do not form adamantane; or R0may represent a direct bond;

[0050] L, L1, L2are independently selected from one of or a combination of a single bond, substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted 7-60 membered heteroarylene, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C60 aryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C2-C60 heteroaryl;

[0051] Z, which is the same or different, is selected from C(Rz) or N, when Z is connected to X1or X2, it is selected from C; E, which is the same or different, is selected from C(Re) or N;

[0052] Rz, Reare independently selected from one of or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C6-C60 aryl, substituted or unsubstituted fused ring group of C3-C30 alicycle and C2-C60 heteroaryl, or adjacent two Rz, adjacent two Reare linked to each other to form a substituted or unsubstituted ring; in the case of two or more Rzand Re, each of the Rzand Reis the same or different;

[0053] At least one of Ar1, Ar2, L1, L2, Rzcontains a group represented by Formula 1-b;

[0054] Ra, Rb, Rcare independently selected from one of or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, or adjacent two groups are linked to each other to form a substituted or unsubstituted ring.

[0055] But the silane-containing indolocarbazole compound of formula 1 excludes the structure shown in formula 1-b1 and formula 1-b2,

[0056]

[0057] Preferably, at least one of Ar1, Ar2, L1, L2, Rz contains a group shown in formula 1-b, and the group 1-b is connected to the aromatic ring or heteroaromatic ring in Ar1, Ar2, L1, L2 or Rz;

[0058] Preferably, the silane-containing indolocarbazole compound is selected from at least one of formula 1-c1, formula 1-c2,

[0059]

[0060] The Or Any position of the adjacent rings is fused.

[0061] Preferably, the silane-containing indolocarbazole compound is selected from at least one of formula 1-1 to formula 1-6,

[0062]

[0063] Preferably, at least one of Ar1, Ar2 is selected from the group shown below (i.e. the group shown in formula 1-a),

[0064]

[0065] The n1 is selected from an integer from 1 to 3, and n2 is selected from an integer from 1 to 4;

[0066] The R0 is the same or different and is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group shown in formula 1-b, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic fused ring group, or adjacent two R0s are bonded to each other to form a substituted or unsubstituted ring, but the two R0s do not form adamantane; or R0 can represent a connecting bond;

[0067] Reare the same or different and are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of substituted or unsubstituted C3-C20 alicyclyl and C6-C30 aryl, a fused ring group of substituted or unsubstituted C3-C20 alicyclyl and C2-C30 heteroaryl, or adjacent two Reare bonded to each other to form a substituted or unsubstituted ring.

[0068] Preferably, at least one of each R0, Reis selected from a group represented by Formula 1-b.

[0069] More preferably, at least one of each Reis selected from a group represented by Formula 1-b.

[0070] Preferably, at least one of Ar1, Ar2is selected from a group represented by Formula 1-a (i.e., a group represented by Formula 1-a),

[0071]

[0072] n1is an integer selected from 1-3, n2is an integer selected from 1-4, n3is an integer selected from 1-6, n4is an integer selected from 1-8, and n5is an integer selected from 1-10;

[0073] R0are the same or different and are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl;

[0074] Reare the same or different and are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl, or adjacent two Reare bonded to each other to form a substituted or unsubstituted ring;

[0075] R1is the same or different selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclo and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclo and C2-C25 heteroaryl, or adjacent two R1s are bonded to each other to form a substituted or unsubstituted ring.

[0076] Preferably, R0is the same or different selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzospirofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzdibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzdibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl;

[0077] Reis the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzospirofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzdibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzdibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, or a combination thereof, or two adjacent Reare bonded to each other to form a substituted or unsubstituted ring.

[0078] R1is the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or a combination thereof, or two adjacent R1are bonded to each other to form a substituted or unsubstituted ring.

[0079] Preferably, at least one of each R0, R1, Reis selected from a group represented by Formula 1-b.

[0080] More preferably, at least one of each Reis selected from a group represented by Formula 1-b.

[0081] Preferably, the Ar1, Ar2is not a group of Formula a-1 selected from one of the following groups or a combination thereof,

[0082]

[0083] M1, M2are independently selected from O, S, N(Rm), C(Rm)2, or Si(Rm)2; Rmis the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring, or a combination thereof, or adjacent two Rmso as to be bonded to each other to form a substituted or unsubstituted ring;

[0084] Y is the same or different selected from C(Ry) or N, R is the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaromatic ring, or a combination thereof, or adjacent two R so as to be bonded to each other to form a substituted or unsubstituted ring.

[0085] Preferably, the Ar1, Ar2is not a group of Formula a-1 selected from one of the following groups or a combination thereof,

[0086]

[0087] m1 is an integer selected from 1-5, m2 is an integer selected from 1-7, m3 is an integer selected from 1-9, m4 is an integer selected from 1-4, m5 is an integer selected from 1-3, m6 is an integer selected from 1-2, m7 is an integer selected from 1-6, m8 is an integer selected from 1-8, m9 is an integer selected from 1-10;

[0088] M1, M2 are independently selected from O, S, N(Rm), C(Rm)2, or Si(Rm)2; Rm is the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C20 alicyclyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C20 alicyclyl and C2-C30 heteroaryl, or a combination thereof, or adjacent two Rm are bonded to each other to form a substituted or unsubstituted ring;

[0089] each R y , R y1 is the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C20 alicyclyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C20 alicyclyl and C2-C30 heteroaryl, or a combination thereof, or adjacent two R y , adjacent two R y1 are bonded to each other to form a substituted or unsubstituted ring;

[0090] R2 is the same or different selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C20 alicyclyl and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C20 alicyclyl and C2-C30 heteroaryl, or a combination thereof, or adjacent two R2 are bonded to each other to form a substituted or unsubstituted ring.

[0091] Preferably, at least one of Rm, R2, Ry, Ry1 is selected from a group represented by Formula 1-b.

[0092] Preferably, Ar1, Ar2 are not a group selected from one of the following groups or a combination thereof,

[0093]

[0094] said m1 is an integer from 1 to 5, m2 is an integer from 1 to 7, m3 is an integer from 1 to 9, m4 is an integer from 1 to 4, m5 is an integer from 1 to 3, m6 is an integer from 1 to 2, m7 is an integer from 1 to 6, m8 is an integer from 1 to 8, m9 is an integer from 1 to 10;

[0095] said R m the same or different one or combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl, or adjacent two Rm are bonded to each other to form a substituted or unsubstituted ring;

[0096] said each R y , R y1 the same or different one or combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl, or adjacent two R y , adjacent two R y1 are bonded to each other to form a substituted or unsubstituted ring;

[0097] said R2 are the same or different one or combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl, or adjacent two R2 are bonded to each other to form a substituted or unsubstituted ring.

[0098] Preferably, said R mone or a combination thereof, or two adjacent R m bonded to each other to form a substituted or unsubstituted ring;

[0099] each R y , R y1one or a combination thereof, or two adjacent R y , two adjacent R y1 bonded to each other to form a substituted or unsubstituted ring;

[0100] R2is the same or different selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted benzospirobifluorenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzo-dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzo-dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted benzocyclobutanyl group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalyl group, a substituted or unsubstituted quinazolyl group, or a combination thereof, or two adjacent R2are bonded to each other to form a substituted or unsubstituted ring.

[0101] Preferably, at least one of Rm, R2, Ry, Ry1is selected from a group represented by Formula 1-b.

[0102] More preferably, at least one of each Ry, Ry1is selected from the group consisting of the group represented by Formula 1-b.

[0103] Preferably, the L, L1, L2are independently selected from the group consisting of a single bond, one of the following groups, or a combination thereof,

[0104]

[0105] the T are the same or different and are selected from the group consisting of C(R t ) or N, and at most 2 T per ring can be N;

[0106] the R t are the same or different and are selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, the group represented by Formula 1-b, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclo and C6-C30 aryl fused ring group, substituted or unsubstituted C3-C20 alicyclo and C2-C30 heteroaryl fused ring group, or a combination thereof, or two adjacent R t bond together to form a substituted or unsubstituted ring.

[0107] Preferably, at least one of each Rtis selected from the group consisting of the group represented by Formula 1-b.

[0108] Preferably, the L, L1, L2are independently selected from the group consisting of a single bond, one of the following groups, or a combination thereof,

[0109]

[0110]

[0111] the e1is selected from an integer from 1 to 4, e2is selected from an integer from 1 to 3, e3is selected from an integer from 1 to 2, e4is selected from an integer from 1 to 6, e5is selected from an integer from 1 to 8, and e6is selected from an integer from 1 to 10;

[0112] the R t are the same or different and are selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, the group represented by Formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclo and C6-C25 aryl fused ring group, substituted or unsubstituted C3-C15 alicyclo and C2-C25 heteroaryl fused ring group, or a combination thereof, or two adjacent Rt are bonded to each other to form a substituted or unsubstituted ring;

[0113] R3is the same or different selected from one of or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl, or adjacent two R3are bonded to each other to form a substituted or unsubstituted ring.

[0114] R3is the same or different selected from one of or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C6-C25 aryl, a fused ring group of substituted or unsubstituted C3-C15 alicyclyl and C2-C25 heteroaryl, or adjacent two R3are bonded to each other to form a substituted or unsubstituted ring.

[0115] R3is the same or different selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, a group represented by Formula 1-b, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, or a combination thereof.

[0116] Preferably, at least one of each R3, R1is selected from a group represented by Formula 1-b.

[0117] More preferably, at least one of each R1is selected from a group represented by Formula 1-b.

[0118] Preferably, the number of groups selected from Formula 1-b in Formula 1 is one, two, three, four, five, six, seven, eight, or more.

[0119] More preferably, the number of groups selected from Formula 1-b in Formula 1 is one, two, three, four, or more.

[0120] Preferably, in the present application, at least one of each Rz, R0, R1, Re, Rm, R2, Ry, Ry1, R3, R1is selected from a group represented by Formula 1-b.

[0121] More preferably, in the present application, at least one of each Rz, Re, Ry, Ry1, R1is selected from a group represented by Formula 1-b.

[0122] Preferably, in the group represented by Formula 1-b,

[0123] L is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted indanylene, substituted or unsubstituted tetrahydronaphthylene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidylene;

[0124] The Ra, Rb, Rc are independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantane, substituted or unsubstituted norbornane, or a combination thereof, or the adjacent two groups are bonded to each other to form a substituted or unsubstituted ring.

[0125] Preferably, the silane-containing indolocarbazole compound is selected from at least one of the following structures,

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] The above lists some specific chemical structures of the silane-containing indolocarbazole compound according to the present application, but the present application is not limited to the listed chemical structures, and any structure based on the structure shown in Formula 1 and having substituents as defined above should be included.

[0149] In addition, the present application also provides an organic electroluminescent device containing the silane-containing indolocarbazole compound according to the present application.

[0150] Preferably, the organic electroluminescent device comprises an anode, an organic layer and a cathode, the organic layer is located between the anode and the cathode, and the organic layer contains the silane-containing indolocarbazole compound according to the present application.

[0151] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer contains the silane-containing indolocarbazole compound according to the present application.

[0152] Preferably, the light-emitting layer comprises a host material, and the host material contains the silane-containing indolocarbazole compound according to the present application.

[0153] The functional layer of the organic electroluminescent device according to the present application can contain at least one of the following functional layers: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cover layer, etc. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties or light extraction properties should be included. Each functional layer can be composed of a single thin film or multiple thin films, and each thin film can be composed of only one material or multiple materials.

[0154] The material of each thin film in the organic electroluminescent device according to the present application is not particularly limited, and any material known in the art can be used. The following describes each organic functional layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device:

[0155] Anode

[0156] The anode material of the present application needs to have a high work function. The anode includes, but is not limited to, materials such as metals or alloys thereof, metal oxides, laminated materials, conductive polymers, etc. Specific examples can include gold (Au), platinum (Pt), nickel (Ni), palladium (Pd), titanium (Ti), indium tin oxide (ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited thereto.

[0157] Cathode

[0158] The cathode material of the present application needs to have a low work function. The cathode includes, but is not limited to, materials such as metals or alloys thereof, laminated materials, etc. Specific examples can include silver (Ag), aluminum (Al), cesium (Cs), calcium (Ca), strontium (Sr), magnesium: silver (Mg:Ag), lithium: aluminum (Li:Al), etc., but are not limited thereto.

[0159] Hole injection layer

[0160] The hole injection material of the present application needs to have good hole injection ability. The hole injection layer includes, but is not limited to, materials such as arylamine derivatives, polycyano conjugated organic compounds, phthalocyanine metal complexes, metal oxides, polymers, etc. Specific examples can include 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (PCzPCA2), 1,4,5,8,9,11-hexaazatriphenylene (HAT-CN), pyrazino[2,3-f][1,10]phenanthroline-2,3-dicyanide (PPDN), copper phthalocyanine (CuPC), tungsten oxide (WO3), poly(4-vinyltriphenylamine) (PVTPA), etc., but are not limited thereto.

[0161] Hole transport layer

[0162] The hole transport material of the present application needs to have high hole mobility and good stability. The hole transport layer includes, but is not limited to, the following materials: arylamine derivatives, carbazole derivatives, polymers, etc. Specific examples can include N4,N4,N4-tris(1,1-biphenyl-4-yl)-N4-(1,1:3,1-terphenyl)-4,4-diamine, tetraphenyl biphenyl diamine (BPBPA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (BSPB), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 44,4'-diphenylmethylenebis(N,N-diphenylphenylamine) (TCBPA), 4,4'-(diphenylsilanediyl)bis(N,N-diphenylphenylamine) (TSBPA), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), poly(4-vinyltriphenylamine) (PVTPA), etc., but are not limited thereto.

[0163] Light-emitting layer

[0164] The light-emitting layer of the present application includes a host material and a dopant material, and the light-emitting material can be a red light-emitting material, a green light-emitting material, a blue light-emitting material, or a combination thereof. The doping ratio of the host material and the dopant material can vary depending on the materials used, and generally the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0165] The host material of the light-emitting layer needs to have not only the bipolar charge transport property, but also the appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. The host material can be one material or two or more materials. The host material includes, but is not limited to, the following materials: heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc., and specific examples can include 9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, 9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, 2,7-bis(diphenylphosphoryl)-9,9'-spirobifluorene (SPPO13), 2,7-bis(carbazol-9-yl)-9,9-spirobifluorene (Spiro-2CBP), 3,5-bis(3-(9H-carbazol-9-yl)phenyl)pyridine (35DCzPPy), 3,3'-bis(dibenzo-thiophene-4-yl)-1,1'-biphenyl (m-BPDBT), 3'-(dibenzo-thiophene-4-yl)-10-phenyl-10H-spiro[acridine-9,9'-fluorene] (STDBT-4), 1,4-bis(9-phenyl-9H-fluoren-9-yl)benzene (pDPFB), tris(8-hydroxyquinoline)aluminum (Alq3), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), etc., but is not limited thereto. The silane-containing indolocarbazole compound of Formula 1 of the present application is preferred. The silane-containing indolocarbazole compound of Formula 1 of the present application can be used as a host material alone or in combination with a p-type host material or an n-type host material, and when used in combination with the p-type host material or the n-type host material, the weight ratio of the silane-containing indolocarbazole compound of Formula 1 of the present application to the p-type host material or the n-type host material is 1:99 to 99:1, and preferably 20:80 to 80:20.

[0166] The dopant material can be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. The dopant material includes, but is not limited to, metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, and the like. Specific examples can include tris[2-(2,4-difluorophenyl)pyridine]iridium (Ir(Fppy)3), bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (FIrPic), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-benzo[H]quinoline-C2,N')acetylacetonate iridium (Ir(bzq)2(acac)), tris[2-(4-n-hexylphenyl)quinoline)iridium (Hex-Ir(phq)3), bis(1-phenyl-isoquinoline)acetylacetonate iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 1,4-bis(4-(9H-carbazol-9-yl)styryl)benzene (BCzSB), 2,5,8,11-tetra-tert-butylperylene (TBPe), 9,10-bis[N,N-di(p-tolyl)amino]anthracene (TTPA), 9,10-bis[N-(m-tolyl)phenylamino]anthracene (TPA), 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljuglavin-9-enyl)-4H-pyran (DCJTB), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), and the like, but are not limited thereto.

[0167] electron transport layer

[0168] The electron transport material of the present application needs to have high electron mobility and good stability. The electron transport layer includes but is not limited to the following materials: metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, heteroaromatic compounds such as imidazole derivatives, phenanthroline derivatives, pyridine derivatives, triazine derivatives, oxadiazole derivatives, etc. Specific examples can include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline) beryllium (Bepq2), 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-phenanthroline[9,10-d]imidazole (ADN-PAimi), 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzimidazole (DNDAPM), 1,3,5-tris(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tris(4-pyridylquinolin-2-yl)benzene (TPyQB), 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)diphenyl (BTB), 2-naphthyl-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,2'-(1,3-phenyl)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole (OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), etc., but not limited thereto.

[0169] Electron injection layer

[0170] The electron injection material of the present application needs to have good hole injection capability. The electron injection layer material includes but is not limited to the following materials: metals, metal compounds, metal oxides, etc. Specific examples can include ytterbium (Yb), lithium 8-hydroxyquinolate (LiQ), calcium fluoride (CaF2), cesium fluoride (CsF), lithium oxide (Li2O), etc., but not limited thereto.

[0171] The method for preparing each layer of thin film in the organic electroluminescent device of the present application is not particularly limited, and can use vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc., but not limited thereto.

[0172] The organic electroluminescent device of the present application is mainly applied to the field of information display technology and lighting, and is widely used in various information displays such as mobile phones, tablet computers, flat panel televisions, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices, etc.

[0173] Synthetic examples

[0174] Starting materials and reagents: The starting materials or reagents used in the following synthetic examples of the present application are not particularly limited, and can be commercially available products or prepared by methods well known to those skilled in the art. The starting materials and reagents used in the present application are all reagent grade.

[0175] Instrument: G2-Si quadrupole time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube type organic elemental analyzer (Elementar, Germany).

[0176] The method for preparing the silane-containing indolocarbazole compound represented by Formula 1 of the present application is not particularly limited, and can employ conventional methods well known to those skilled in the art. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc., the silane-containing indolocarbazole compound represented by Formula 1 of the present application can be prepared, for example, using the synthetic route shown below.

[0177]

[0178] The Xn is halogen, for example, Xn is the same or different selected from Cl, Br, I.

[0179] [Synthesis Example 1] Synthesis of Compound 3

[0180]

[0181] Under nitrogen protection, a-3 (12.67 g, 30.00 mmol), b-3 (10.31 g, 45.00 mmol), copper powder (2.86 g, 45.00 mmol), potassium carbonate (12.44 g, 90.00 mmol), 18-crown-6 (634 mg, 2.40 mmol) and 1,2-dichlorobenzene (400 ml) were added to a reaction bottle, and stirred under reflux conditions for 15 hours. After the reaction was completed, distilled water was first added, and then extracted with ethyl acetate, and the organic phase was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, recrystallized with toluene to obtain compound 3 (12.84 g, yield 75%); the solid purity was detected by HPLC ≧ 99.96%. Mass spectrum m / z: 570.2139 (theoretical value: 570.2127). Theoretical elemental content (%) C 39 H 30 N2OSi: C, 82.07; H, 5.30; N, 4.91. Measured elemental content (%) : C, 82.05; H, 5.33; N, 4.94.

[0182] [Synthesis Example 2] Synthesis of Compound 15

[0183]

[0184] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-15, b-15 respectively to obtain compound 15 (14.74 g, yield 69%); HPLC purity ≥ 99.90%. Mass spectrum m / z: 711.2722 (theoretical value: 711.2706). Theoretical elemental content (%) C 49 H 37 N3OSi: C, 82.67; H, 5.24; N, 5.90. Actual elemental content (%) C, 82.64; H, 5.25; N, 5.94.

[0185] [Synthesis Example 3] Synthesis of compound 16

[0186]

[0187] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-16, b-16 respectively to obtain compound 16 (16.15 g, yield 71%); HPLC purity ≥ 99.91%. Mass spectrum m / z: 757.3081 (theoretical value: 757.3070). Theoretical elemental content (%) C 51 H 45 N2OSi2: C, 80.80; H, 5.98; N, 3.70. Actual elemental content (%) C, 80.83; H, 5.95; N, 3.72.

[0188] [Synthesis Example 4] Synthesis of compound 29

[0189]

[0190] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-29, b-29 respectively to obtain compound 29 (15.44 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 704.2695 (theoretical value: 704.2681). Theoretical elemental content (%) C 48 H 40 N2SSi: C, 81.78; H, 5.72; N, 3.97. Actual elemental content (%) C, 81.75; H, 5.74; N, 3.94.

[0191] [Synthesis Example 5] Synthesis of compound 36

[0192]

[0193] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-29, b-29 respectively to obtain compound 29 (18.68 g, yield 75%); HPLC purity ≥ 99.92%. Mass spectrum m / z: 829.3864 (theoretical value: 829.3852). Theoretical elemental content (%) C 59 H 51 N3Si: C, 85.36; H, 6.19; N, 5.06. Actual elemental content (%) : C, 85.38; H, 6.16; N, 5.09.

[0194] [Synthesis Example 6] Synthesis of compound 51

[0195]

[0196] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-29, b-29 respectively to obtain compound 29 (18.68 g, yield 75%); HPLC purity ≥ 99.92%. Mass spectrum m / z: 829.3864 (theoretical value: 829.3852). Theoretical elemental content (%) C 54 H 44 N2Si: C, 86.59; H, 5.92; N, 3.74. Actual elemental content (%) : C, 86.54; H, 5.94; N, 3.77.

[0197] [Synthesis Example 7] Synthesis of compound 60

[0198]

[0199] According to the preparation method of synthesis example 1, replace equal moles of a-3 with equal moles of a-60 respectively to obtain compound 60 (15.05 g, yield 72%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 696.2581 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Actual elemental content (%) : C, 84.42; H, 5.24; N, 4.04.

[0200] [Synthesis Example 8] Synthesis of compound 63

[0201]

[0202] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-63, b-63 respectively, to obtain compound 63 (15.26 g, yield 73%); HPLC purity ≥ 99.95%. Mass spectrum m / z: 696.2587 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Measured elemental content (%) C, 84.49; H, 5.18; N, 4.05.

[0203] [Synthesis Example 9] Synthesis of compound 90

[0204]

[0205] According to the preparation method of synthesis example 1, replace equal moles of a-3 with equal moles of a-90 respectively, to obtain compound 90 (15.66 g, yield 75%); HPLC purity ≥ 99.96%. Mass spectrum m / z: 695.2763 (theoretical value: 695.2757). Theoretical elemental content (%) C 49 H 37 N3Si: C, 84.57; H, 5.36; N, 6.04. Measured elemental content (%) C, 84.58; H, 5.33; N, 6.03.

[0206] [Synthesis Example 10] Synthesis of compound 94

[0207]

[0208] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-94, b-94 respectively, to obtain compound 94 (15.26 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 696.2724 (theoretical value: 696.2709). Theoretical elemental content (%) C 48 H 36 N4Si: C, 82.72; H, 5.21; N, 8.04. Measured elemental content (%) C, 82.73; H, 5.25; N, 8.02.

[0209] [Synthesis Example 11] Synthesis of compound 98

[0210]

[0211] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-63, b-98, respectively, to obtain compound 98 (16.68 g, yield 72%); HPLC purity ≥ 99.93%. Mass spectrum m / z: 771.3083 (theoretical value: 771.3070). Theoretical elemental content (%) C 55 H 41 N3Si: C, 85.57; H, 5.35; N, 5.44. Actual elemental content (%) : C, 85.53; H, 5.33; N, 5.46.

[0212] [Synthesis example 12] synthesis of compound 101

[0213]

[0214] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-101, b-101, respectively, to obtain compound 101 (16.47 g, yield 71%); HPLC purity ≥ 99.92%. Mass spectrum m / z: 772.3289 (theoretical value: 772.3274). Theoretical elemental content (%) C 56 H 44 N2Si: C, 87.01; H, 5.74; N, 3.62. Actual elemental content (%) : C, 87.04; H, 5.71; N, 3.65.

[0215] [Synthesis example 13] synthesis of compound 104

[0216]

[0217] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-104, b-104, respectively, to obtain compound 104 (15.62 g, yield 72%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 722.3125 (theoretical value: 722.3117). Theoretical elemental content (%) C 52 H 42 N2Si: C, 86.39; H, 5.86; N, 3.87. Actual elemental content (%) : C, 86.35; H, 5.87; N, 3.85.

[0218] [Synthesis example 14] synthesis of compound 141

[0219]

[0220] Preparation of A-141:

[0221] To a reaction flask was added c-141 (27.69 g, 110.00 mmol), b-3 (37.82 g, 165.00 mmol), copper powder (10.49 g, 165.00 mmol), potassium carbonate (45.61 g, 330.00 mmol), 18-crown-6 (2.33 g, 8.80 mmol) and 1,2-dichlorobenzene (1.5 L) under nitrogen protection, and stirred at reflux for 12 hours. After the reaction was completed, distilled water was first added, and then extraction was performed with dichloromethane. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Recrystallization was performed with ethyl acetate:n-hexane = 2:1 to obtain A-141 (36.08 g, yield 82%); the solid purity was ≧99.85% as detected by HPLC.

[0222] Preparation of B-141:

[0223] To a reaction flask was added A-141 (36.00 g, 90.00 mmol), bis(pinacolato)diboron (22.85 g, 90.00 mmol), (1,1'-bis(diphenylphosphino)ferrocene)palladium dichloride (196 mg, 0.27 mmol), potassium acetate (17.67 g, 180.00 mmol), DMF (450 ml) under nitrogen protection, and stirred at reflux for 8 hours. After the reaction was completed, it was cooled to room temperature, the solvent was removed under reduced pressure, water was added, extraction was performed with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallization was performed with toluene:methanol = 4:1 to obtain B-141 (37.60 g, 85%); the solid purity was ≧99.80% as detected by HPLC.

[0224] Preparation of C-141:

[0225] To a reaction flask was added B-141 (34.41 g, 70.00 mmol), e-141 (14.14 g, 70.00 mmol), tetrakis(triphenylphosphine)palladium (809 mg, 0.70 mmol), potassium carbonate (14.51 g, 105.00 mmol), tetrahydrofuran (300 ml), water (150 ml) under nitrogen protection, and stirred at reflux for 7.5 hours. After the reaction was completed, it was cooled to room temperature, the solvent was removed under reduced pressure, water was added, extraction was performed with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallization was performed with toluene:n-hexane = 5:1 to obtain C-141 (25.21 g, 74%); the solid purity was ≧99.82% as detected by HPLC.

[0226] Preparation of D-141:

[0227] To a reaction flask under nitrogen protection was added C-141 (24.33 g, 50.00 mmol), triphenylphosphine (32.79, 125.00 mmol), o-dichlorobenzene (300 ml), and stirred at reflux for 10 hours. After the reaction was completed, it was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and extraction was performed with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallization was performed with ethyl acetate: petroleum ether = 7: 1 to obtain D-141 (17.28 g, 76%); the solid purity was ≧99.89% by HPLC.

[0228] Preparation of compound 141:

[0229] To a reaction flask under nitrogen protection was added D-141 (13.64 g, 30.00 mmol), f-141 (12.54 g, 45.00 mmol), copper powder (2.86 g, 45.00 mmol), potassium carbonate (12.44 g, 90.00 mmol), 18-crown-6 (634 mg, 2.4 mmol), and 1,2-dichlorobenzene (400 ml), and stirred at reflux for 16 hours. After the reaction was completed, distilled water was added first, and then extraction was performed with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by distillation under reduced pressure, and recrystallization was performed with toluene to obtain compound 141 (15.05 g, yield 72%); the solid purity was ≧99.93% by HPLC. Mass m / z: 696.2579 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Measured elemental content (%): C, 84.43; H, 5.24; N, 4.04.

[0230] [Synthesis Example 15] Synthesis of compound 147

[0231]

[0232]

[0233] According to the preparation method of synthesis example 14, equimolar f-141 was replaced with equimolar f-147 to obtain compound 147 (15.61 g); the HPLC purity was ≧99.94%. Mass m / z: 712.2375 (theoretical value: 712.2368). Theoretical elemental content (%) C 49 H 36 N2SSi: C, 82.55; H, 5.09; N, 3.93. Measured elemental content (%): C, 82.51; H, 5.07; N, 3.96.

[0234] [Synthesis Example 16] Synthesis of compound 149

[0235]

[0236] According to the preparation method of synthesis example 14, replace equal moles of c-141, f-141 with equal moles of c-149, f-149, respectively, to obtain compound 149 (17.51 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 821.3238 (theoretical value: 821.3226). Theoretical elemental content (%) C 59 H 43 N3Si: C, 86.20; H, 5.27; N, 5.11. Measured elemental content (%) : C, 86.23; H, 5.25; N, 5.13.

[0237] [Synthesis Example 17] Synthesis of compound 159

[0238]

[0239] According to the preparation method of synthesis example 14, replace equal moles of c-141, b-3, f-141 with equal moles of c-159, b-159, f-159, respectively, to obtain compound 159 (14.97 g); HPLC purity ≥ 99.90%. Mass spectrum m / z: 712.2379 (theoretical value: 712.2368). Theoretical elemental content (%) C 49 H 36 N2SSi: C, 82.55; H, 5.09; N, 3.93. Measured elemental content (%) : C, 82.58; H, 5.05; N, 3.95.

[0240] [Synthesis Example 18] Synthesis of compound 161

[0241]

[0242] According to the preparation method of synthesis example 14, replace equal moles of c-141, b-3, f-141 with equal moles of c-161, b-161, f-161, respectively, to obtain compound 161 (16.30 g); HPLC purity ≥ 99.89%. Mass spectrum m / z: 798.3819 (theoretical value: 798.3806). Theoretical elemental content (%) C 56 H 51 FN2Si: C, 84.17; H, 6.43; N, 3.51. Measured elemental content (%) : C, 84.14; H, 6.47; N, 3.53.

[0243] Synthesis of compound 162

[0244]

[0245] According to the preparation method of synthetic example 14, replace equal moles of b-3, f-141 with equal moles of b-162, f-162 respectively, to obtain compound 162 (16.93g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 772.3283 (theoretical value: 772.3274). Theoretical elemental content (%) C 56 H 44 N2Si: C, 87.01; H, 5.74; N, 3.62. The measured elemental content (%) of C, 87.04; H, 5.72; N, 3.60.

[0246] Synthesis of compound 227

[0247]

[0248] According to the preparation method of synthetic example 1, replace equal moles of a-3 with equal moles of a-227 respectively, to obtain compound 227 (14.92g, yield 77%); HPLC purity ≥ 99.95%. Mass spectrum m / z: 645.2618 (theoretical value: 645.2600). Theoretical elemental content (%) C 45 H 35 N3Si: C, 83.68; H, 5.46; N, 6.51. The measured elemental content (%) of C, 83.66; H, 5.43; N, 6.54.

[0249] Synthesis of compound 271

[0250]

[0251] Under the protection of nitrogen, g-271 (12.02g, 30.00mmol), h-271 (14.82g, 60.00mmol), copper powder (5.72g, 90.00mmol), potassium carbonate (24.88g, 180.00mmol), 18-crown-6 (1.27g, 4.8mmol) and 1,2-dichlorobenzene (600ml) were added into the reaction bottle, and stirred under reflux conditions for 20 hours. After the reaction was completed, distilled water was first added, and then extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, recrystallized with toluene to obtain compound 271 (16.27g, yield 74%); HPLC solid purity ≧ 99.95%. Mass spectrum m / z: 732.2641 (theoretical value: 732.2628). Theoretical elemental content (%) C48 H 40 N2O2Si2: C, 78.65; H, 5.50; N, 3.82. Found (mass %): C, 78.67; H, 5.54; N, 3.81.

[0252] [Synthesis Example 22] Synthesis of compound 274

[0253]

[0254] According to the preparation method of synthesis example 23, replace equal moles of h-271 with equal moles of h-274, respectively, to obtain compound 274 (17.20 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 784.3656 (theoretical value: 784.3669). Theoretical elemental content (%) C 54 H 52 N2Si2: C, 82.60; H, 6.68; N, 3.57. Found (mass %): C, 82.65; H, 6.64; N, 3.53.

[0255] [Synthesis Example 23] Synthesis of compound 301

[0256]

[0257] According to the preparation method of synthesis example 1, replace equal moles of a-3 with equal moles of a-301, respectively, to obtain compound 301 (15.68 g, yield 75%); HPLC purity ≥ 99.96%. Mass spectrum m / z: 696.2580 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Found (mass %): C, 84.47; H, 5.24; N, 4.01.

[0258] [Synthesis Example 24] Synthesis of compound 315

[0259]

[0260] According to the preparation method of synthesis example 1, replace equal moles of a-3 with equal moles of a-315, respectively, to obtain compound 315 (14.32 g, yield 76%); HPLC purity ≥ 99.97%. Mass spectrum m / z: 627.2739 (theoretical value: 627.2723). Theoretical elemental content (%) C 43 H 25D7N2OSi: C, 82.26; H, 6.26; N, 4.46. Found (mass %): C, 82.27; H, 6.22; N, 4.48.

[0261] [Synthesis Example 25] Synthesis of compound 321

[0262]

[0263] According to the preparation method of synthesis example 1, replace equal moles of a-3, b-3 with equal moles of a-321, b-321, respectively, to obtain compound 321 (15.26 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 696.2585 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Found (mass %): C, 84.46; H, 5.24; N, 4.03.

[0264] [Synthesis Example 26] Synthesis of compound 334

[0265]

[0266] According to the preparation method of synthesis example 14, replace equal moles of c-141 with equal moles of c-334, respectively, to obtain compound 334 (15.47 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 696.2585 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Found (mass %): C, 84.46; H, 5.24; N, 4.03.

[0267] [Synthesis Example 27] Synthesis of compound 352

[0268]

[0269] According to the preparation method of synthesis example 1, replace equal moles of a-3 with equal moles of a-352, respectively, to obtain compound 352 (17.11 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 780.3401 (theoretical value: 780.3412). Theoretical elemental content (%) C 55 H 32 D8N2OSi: C, 84.58; H, 6.19; N, 3.59. Found (mass %): C, 84.55; H, 6.18; N, 3.56.

[0270] [Synthesis Example 28] Synthesis of compound 423

[0271]

[0272] According to the preparation method of Synthesis Example 1, replace equal moles of a-3 with equal moles of a-423, respectively, to obtain compound 423 (16.13 g, yield 75%); HPLC purity ≥ 99.96%. Mass spectrum m / z: 716.2634 (theoretical value: 716.2620). Theoretical elemental content (%) C 49 H 32 D4N2SSi: C, 82.08; H, 5.62; N, 3.91. Measured elemental content (%) C, 82.06; H, 5.65; N, 3.93.

[0273] [Synthesis Example 29] Synthesis of compound 434

[0274]

[0275] According to the preparation method of Synthesis Example 1, replace equal moles of a-3, b-3 with equal moles of a-434, b-434, respectively, to obtain compound 434 (16.36 g, yield 74%); HPLC purity ≥ 99.95%. Mass spectrum m / z: 736.2374 (theoretical value: 736.2368). Theoretical elemental content (%) C 51 H 36 N2SSi: C, 83.11; H, 4.92; N, 3.80. Measured elemental content (%) C, 83.13; H, 4.91; N, 3.83.

[0276] [Synthesis Example 30] Synthesis of compound 442

[0277]

[0278] According to the preparation method of Synthesis Example 1, replace equal moles of a-3 with equal moles of a-442, respectively, to obtain compound 442 (16.49 g, yield 79%); HPLC purity ≥ 99.99%. Mass spectrum m / z: 695.2766 (theoretical value: 695.2757). Theoretical elemental content (%) C 49 H 37 N3Si: C, 84.57; H, 5.36; N, 6.04. Measured elemental content (%) C, 84.56; H, 5.38; N, 6.01.

[0279] [Synthesis Example 31] Synthesis of compound 452

[0280]

[0281] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-452, respectively, to obtain compound 452 (16.38 g, yield 78%); HPLC purity ≥ 99.98%. Mass spectrum m / z: 699.3023 (theoretical value: 699.3008). Theoretical elemental content (%) C 49 H 33 D4N3Si: C, 84.08; H, 5.90; N, 6.00. Measured elemental content (%) C, 84.05; H, 5.92; N, 6.04.

[0282] [Synthetic Example 32] Synthesis of compound 457

[0283]

[0284] According to the preparation method of Synthetic Example 15, replace equal moles of D-141, f-141 with equal moles of D-334, f-457, respectively, to obtain compound 457 (17.60 g, yield 76%); HPLC purity ≥ 99.97%. Mass spectrum m / z: 771.3086 (theoretical value: 771.3070). Theoretical elemental content (%) C 55 H 41 N3Si: C, 85.57; H, 5.35; N, 5.44. Measured elemental content (%) C, 85.58; H, 5.33; N, 5.47.

[0285] [Synthetic Example 33] Synthesis of compound 475

[0286]

[0287] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-475, respectively, to obtain compound 475 (15.14 g, yield 78%); HPLC purity ≥ 99.99%. Mass spectrum m / z: 646.2815 (theoretical value: 646.2804). Theoretical elemental content (%) C 46 H 38 N2Si: C, 85.41; H, 5.92; N, 4.33. Measured elemental content (%) C, 85.44; H, 5.95; N, 4.31.

[0288] [Synthetic Example 34] Synthesis of compound 476

[0289]

[0290] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-321, b-476, respectively, to obtain compound 476 (16.27 g, yield 75%); HPLC purity ≥ 99.96%. Mass spectrum m / z: 722.3135 (theoretical value: 722.3117). Theoretical elemental content (%) C 52 H 42 N2Si: C, 86.39; H, 5.86; N, 3.87. Actual elemental content (%) C, 86.36; H, 5.85; N, 3.89.

[0291] [Synthesis Example 35] Synthesis of compound 492

[0292]

[0293] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-475, b-29, respectively, to obtain compound 492 (15.71 g, yield 76%); HPLC purity ≥ 99.97%. Mass spectrum m / z: 688.3261 (theoretical value: 688.3274). Theoretical elemental content (%) C 49 H 44 N2Si: C, 86.39; H, 5.86; N, 3.87. Actual elemental content (%) C, 86.36; H, 5.85; N, 3.89.

[0294] [Synthesis Example 36] Synthesis of compound 561

[0295]

[0296] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-561, b-561, respectively, to obtain compound 561 (13.07 g, yield 73%); HPLC purity ≥ 99.91%. Mass spectrum m / z: 596.2051 (theoretical value: 596.2032). Theoretical elemental content (%) C 39 H 28 N4OSi: C, 78.49; H, 4.73; N, 9.39. Actual elemental content (%) C, 78.48; H, 4.76; N, 9.35.

[0297] [Synthesis Example 37] Synthesis of compound 575

[0298]

[0299] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-575, respectively, to obtain compound 575 (16.01 g, yield 74%); HPLC purity ≥ 99.95%. Mass spectrum m / z: 720.2975 (theoretical value: 720.2961). Theoretical elemental content (%) C 52 H 40 N2Si: C, 86.63; H, 5.59; N, 3.89. Measured elemental content (%) C, 86.66; H, 5.55; N, 3.87.

[0300] [Synthesis Example 38] Synthesis of compound 582

[0301]

[0302] According to the preparation method of Synthetic Example 23, replace equal moles of g-271, h-271 with equal moles of g-582, h-582, respectively, to obtain compound 582 (18.95 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 864.2496 (theoretical value: 864.2484). Theoretical elemental content (%) C 56 H 44 N2S2Si2: C, 77.73; H, 5.13; N, 3.24. Measured elemental content (%) C, 77.76; H, 5.12; N, 3.27.

[0303] [Synthesis Example 39] Synthesis of compound 585

[0304]

[0305] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-585, b-585, respectively, to obtain compound 585 (14.19 g, yield 72%); HPLC purity ≥ 99.88%. Mass spectrum m / z: 656.2275 (theoretical value: 656.2284). Theoretical elemental content (%) C 46 H 32 N2OSi: C, 84.11; H, 4.91; N, 4.26. Measured elemental content (%) C, 84.16; H, 4.92; N, 4.23.

[0306] [Synthesis Example 40] Synthesis of compound 603

[0307]

[0308] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-603, respectively, to obtain compound 603 (13.97 g, yield 75%); HPLC purity ≥ 99.96%. Mass spectrum m / z: 620.2297 (theoretical value: 620.2284). Theoretical elemental content (%) C 43 H 32 N2OSi: C, 83.19; H, 5.20; N, 4.51. Measured elemental content (%) C, 83.16; H, 5.22; N, 4.54.

[0309] [Synthesis Example 41] Synthesis of compound 639

[0310]

[0311] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-639, respectively, to obtain compound 639 (14.14 g, yield 74%); HPLC purity ≥ 99.95%. Mass spectrum m / z: 636.2071 (theoretical value: 636.2055). Theoretical elemental content (%) C 43 H 32 N2SSi: C, 81.09; H, 5.06; N, 4.40. Measured elemental content (%) C, 81.08; H, 5.03; N, 4.42.

[0312] [Synthesis Example 42] Synthesis of compound 640

[0313]

[0314] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-640, b-640, respectively, to obtain compound 640 (15.97 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 728.2694 (theoretical value: 728.2681). Theoretical elemental content (%) C 50 H 40 N2SSi: C, 82.38; H, 5.53; N, 3.84. Measured elemental content (%) C, 82.36; H, 5.56; N, 3.85.

[0315] [Synthesis Example 43] Synthesis of compound 650

[0316]

[0317] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-639, b-650, respectively, to obtain compound 650 (14.37 g, yield 65%); HPLC purity ≥ 99.90%. Mass spectrum m / z: 736.2381 (theoretical value: 736.2368). Theoretical elemental content (%) C 51 H 36 N2SSi: C, 83.11; H, 4.92; N, 3.80. Measured elemental content (%) C, 83.14; H, 4.89; N, 3.84.

[0318] [Synthesis Example 44] Synthesis of compound 682

[0319]

[0320] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-682, respectively, to obtain compound 682 (14.84 g, yield 71%); HPLC purity ≥ 99.92%. Mass spectrum m / z: 696.2585 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Measured elemental content (%) C, 84.46; H, 5.20; N, 4.04.

[0321] [Synthesis Example 45] Synthesis of compound 689

[0322]

[0323] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-689, b-689, respectively, to obtain compound 689 (18.28 g, yield 68%); HPLC purity ≥ 99.89%. Mass spectrum m / z: 895.3394 (theoretical value: 895.3383). Theoretical elemental content (%) C 65 H 45 N3Si: C, 87.12; H, 5.06; N, 4.69. Measured elemental content (%) C, 87.15; H, 5.09; N, 4.65.

[0324] [Synthesis Example 46] Synthesis of compound 689

[0325]

[0326] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-693, b-693, respectively, to obtain compound 693 (14.64 g, yield 70%); HPLC purity ≥ 99.88%. Mass spectrum m / z: 696.2973 (theoretical value: 696.2961). Theoretical elemental content (%) C 50 H 40 N2Si: C, 86.17; H, 5.79; N, 4.02. Measured elemental content (%) C, 86.15; H, 5.76; N, 4.05.

[0327] [Synthesis Example 47] Synthesis of compound 695

[0328]

[0329] According to the preparation method of Synthetic Example 14, replace equal moles of c-141, f-141 with equal moles of c-695, f-695, respectively, to obtain compound 695 (16.65 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 770.3126 (theoretical value: 770.3117). Theoretical elemental content (%) C 56 H 42 N2Si: C, 87.23; H, 5.49; N, 3.63. Measured elemental content (%) C, 87.25; H, 5.46; N, 3.66.

[0330] [Synthesis Example 48] Synthesis of compound 705

[0331]

[0332] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-705, b-705, respectively, to obtain compound 705 (15.05 g, yield 72%); HPLC purity ≥ 99.93%. Mass spectrum m / z: 696.2581 (theoretical value: 696.2597). Theoretical elemental content (%) C 49 H 36 N2OSi: C, 84.45; H, 5.21; N, 4.02. Measured elemental content (%) C, 84.44; H, 5.23; N, 4.05.

[0333] [Synthesis Example 49] Synthesis of compound 710

[0334]

[0335] According to the preparation method of Synthetic Example 14, replace equal moles of c-141, b-3, f-141 with equal moles of c-710, d-710, b-36, respectively, to obtain compound 710 (15.68 g); HPLC purity ≥ 99.92%. Mass spectrum m / z: 735.3083 (theoretical value: 735.3070). Theoretical elemental content (%) C 52 H 41 N3Si: C, 84.86; H, 5.62; N, 5.71. Measured elemental content (%) C, 84.88; H, 5.61; N, 5.75.

[0336] [Synthesis Example 50] Synthesis of compound 713

[0337]

[0338] According to the preparation method of Synthetic Example 14, replace equal moles of c-141, f-141 with equal moles of c-710, b-36, respectively, to obtain compound 713 (16.13 g); HPLC purity ≥ 99.90%. Mass spectrum m / z: 767.3164 (theoretical value: 767.3152). Theoretical elemental content (%) C 52 H 45 N3Si2: C, 81.31; H, 5.91; N, 5.47. Measured elemental content (%) C, 81.34; H, 5.93; N, 5.44.

[0339] [Synthesis Example 51] Synthesis of compound 714

[0340]

[0341]

[0342] According to the preparation method of Synthetic Example 14, replace equal moles of c-141, f-141 with equal moles of c-714, f-714, respectively, to obtain compound 714 (15.62 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 722.3126 (theoretical value: 722.3117). Theoretical elemental content (%) C 52 H 42 N2Si: C, 86.39; H, 5.86; N, 3.87. Measured elemental content (%) C, 86.35; H, 5.88; N, 3.84.

[0343] [Synthesis Example 52] Synthesis of compound 727

[0344]

[0345] According to the preparation method of Synthetic Example 1, replace equal moles of a-3 with equal moles of a-727, respectively, to obtain compound 727 (15.81 g, yield 73%); HPLC purity ≥ 99.94%. Mass spectrum m / z: 721.2926 (theoretical value: 721.2913). Theoretical elemental content (%) C 51 H 39 N3Si: C, 84.84; H, 5.45; N, 5.82. Measured elemental content (%) C, 84.86; H, 5.41; N, 5.85.

[0346] [Synthesis Example 53] Synthesis of compound 730

[0347]

[0348] According to the preparation method of Synthetic Example 14, replace equal moles of f-141 with equal moles of f-730 to obtain compound 730 (18.76 g); HPLC purity ≥ 99.93%. Mass spectrum m / z: 844.3285 (theoretical value: 844.3274). Theoretical elemental content (%) C 62 H 44 N2Si: C, 88.11; H, 5.25; N, 3.31. Measured elemental content (%) C, 88.14; H, 5.23; N, 3.33.

[0349] [Synthesis Example 54] Synthesis of compound 886

[0350]

[0351] According to the preparation method of Synthetic Example 1, replace equal moles of a-3, b-3 with equal moles of a-475, b-886, respectively, to obtain compound 886 (14.72 g, yield 70%); HPLC purity ≥ 99.89%. Mass spectrum m / z: 700.3286 (theoretical value: 700.3274). Theoretical elemental content (%) C 50 H 44 N2Si: C, 85.67; H, 6.33; N, 4.00. Measured elemental content (%) C, 85.63; H, 6.31; N, 4.03.

[0352] Device Example

[0353] In the present application, the ITO glass substrate is ultrasonically cleaned with 5% glass cleaning solution for 2 times, 20 minutes each time, and then ultrasonically cleaned with deionized water for 2 times, 10 minutes each time. Ultrasonic cleaning with acetone and isopropyl alcohol is performed in sequence for 20 minutes, and dried at 120°C. The organic materials are all sublimed, and the purity is all above 99.99%.

[0354] A test software, a computer, a K2400 digital source meter produced by Keithley Company of USA and a PR788 spectral scanning luminance meter of PhotoResearch Company of USA were combined into a joint IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of the organic electroluminescent device. The test of the service life was performed by using an M6000 OLED service life test system of McScience Company. The test environment was an atmospheric environment, and the temperature was room temperature.

[0355] Example 1: Preparation of an organic electroluminescent device 1

[0356] HAT-CN was vacuum-evaporated on an ITO anode as a hole injection layer, with a thickness of 10 nm; BPBPA was vacuum-evaporated on the hole injection layer as a hole transport layer, with a thickness of 48 nm; compound 3 of the application and EM-1 were vacuum-evaporated on the hole transport layer as a host at a ratio of 1:1 (wt%) and the dopant Ir(ppy)2(acac) was evaporated at a doping amount of 10 wt% based on the total amount of the host and the dopant to form a light-emitting layer, with a thickness of 40 nm; DNDAPM: Liq = 1:1 (wt%) was vacuum-evaporated on the light-emitting layer as an electron transport layer, with a thickness of 48 nm; Yb was vacuum-evaporated on the electron transport layer as an electron injection layer, with an evaporation thickness of 1 nm; Al was vacuum-evaporated on the electron injection layer as a cathode, with a thickness of 150 nm.

[0357] Examples 2-30: Preparation of organic electroluminescent devices 2-30

[0358] Compound 3 in the light-emitting layer of Example 1 was replaced by compound 16, compound 29, compound 60, compound 63, compound 90, compound 98, compound 101, compound 147, compound 162, compound 227, compound 271, compound 274, compound 301, compound 315, compound 334, compound 352, compound 442, compound 452, compound 457, compound 475, compound 561, compound 575, compound 585, compound 639, compound 640, compound 682, compound 705, compound 714, compound 730, respectively, and the other steps were the same, to obtain organic electroluminescent devices 2-30.

[0359] Comparative Examples 1-7: Preparation of comparative organic electroluminescent devices 1-7

[0360] Compound 3 in the light-emitting layer of Example 1 was replaced by R-1, R-2, R-3, R-4, R-5, R-6, R-7, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 1-7.

[0361]

[0362]

[0363] The test results of the light-emitting properties of the organic electroluminescent devices prepared in Examples 1-30 and Comparative Examples 1-7 are shown in Table 1.

[0364] Table 1 Test data of the light-emitting properties of the organic electroluminescent devices

[0365]

[0366]

[0367] According to Table 1, the organic electroluminescent device of the present application has good photoelectric performance, specifically, low driving voltage, high luminous efficiency, and long service life.

[0368] Example 31: Preparation of organic electroluminescent device 31

[0369] HAT-CN was vacuum-evaporated on the ITO anode as a hole injection layer, with a thickness of 10 nm; HT-1 was vacuum-evaporated on the hole injection layer as a hole transport layer, with a thickness of 50 nm; the compound 3 of the present application and EM-2 were vacuum-evaporated on the hole transport layer as a host at a ratio of 1:1 (wt%) and the dopant Hex-Ir(phq)3 was evaporated at a doping amount of 6 wt% based on the total amount of the host and the dopant to form a light-emitting layer, with a thickness of 40 nm; AND-PAimi:Liq = 1:1 (wt%) was vacuum-evaporated on the light-emitting layer as an electron transport layer, with a thickness of 50 nm; Yb was vacuum-evaporated on the electron transport layer as an electron injection layer, with an evaporation thickness of 1 nm; Al was vacuum-evaporated on the electron injection layer as a cathode, with a thickness of 150 nm.

[0370] Examples 32-61: Preparation of organic electroluminescent devices 32-61

[0371] The compound 3 in the light-emitting layer of Example 31 was replaced by compound 15, compound 36, compound 51, compound 94, compound 104, compound 141, compound 147, compound 149, compound 159, compound 161, compound 301, compound 321, compound 334, compound 423, compound 434, compound 457, compound 476, compound 492, compound 575, compound 582, compound 603, compound 650, compound 689, compound 693, compound 695, compound 710, compound 713, compound 714, compound 727, and compound 886, respectively, and the other steps were the same, to obtain organic electroluminescent devices 32-61.

[0372] Preparation of Comparative Organic Electroluminescence Devices 8-14

[0373] The compound 3 in the light-emitting layer of Example 31 was replaced by R-1, R-2, R-3, R-4, R-5, R-6, R-7 respectively, and other steps were the same, to obtain Comparative Organic Electroluminescence Devices 8-14.

[0374]

[0375] The luminescent properties of the organic electroluminescence devices prepared in Examples 31-61 and Comparative Examples 8-14 were tested, and the results are shown in Table 2.

[0376] Table 2 Luminescent properties test data of organic electroluminescence devices

[0377]

[0378]

[0379] According to Table 2, the organic electroluminescence device of the present application has good photoelectric performance, specifically, the driving voltage is low, the luminous efficiency is high, and the service life is long.

[0380] It should be noted that the present application is particularly described with individual embodiments, but those skilled in the art can make various forms or details of improvement to the present application without departing from the principles of the present application, and these improvements also fall within the protection scope of the present application.

Claims

1. A silane-containing indolocarbazole compound characterized in that, The silane-containing indolocarbazole compound is selected from at least one of the following Formula 1-1 to Formula 1-6, At least one of the Ar1, Ar2 is selected from a group represented by Formula 1-a, which is selected from a group represented by the following formula, The n1 is selected from an integer of 1 to 3, the n2 is selected from an integer of 1 to 4, the n3 is selected from an integer of 1 to 6, the n4 is selected from an integer of 1 to 8, and the n5 is selected from an integer of 1 to 10; The R0 is the same or different and is selected from one of hydrogen, deuterium, tritium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group; said R 01 one, identical or different, selected from the group consisting of a group according to formula 1-b, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group; The Re is the same or different and is selected from one of hydrogen, deuterium, tritium, a cyano group, a halogen, a group represented by Formula 1-b, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, and a substituted or unsubstituted phenyl group, or adjacent two Re are bonded to each other to form a substituted or unsubstituted benzene ring; The R1 is the same or different and is selected from one of hydrogen, deuterium, tritium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, and a substituted or unsubstituted pentyl group; The Ar1, Ar2 is not the 1-a group and is selected from one of a group represented by the following formula, The m1 is selected from an integer of 1 to 5, the m2 is selected from an integer of 1 to 7, the m3 is selected from an integer of 1 to 9, the m4 is selected from an integer of 1 to 4, the m5 is selected from an integer of 1 to 3, the m7 is selected from an integer of 1 to 6, the m8 is selected from an integer of 1 to 8, and the m9 is selected from an integer of 1 to 10; The R y The same or different from one selected from hydrogen, deuterium, tritium, cyano, halogen, group shown in formula 1-b, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl; The R2 is the same or different and is selected from one of hydrogen, deuterium, tritium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, and a substituted or unsubstituted pentyl group; The L is selected from a single bond or one of a group represented by the following formula, The L1, L2 is independently selected from a single bond or one of a group represented by the following formula, The e1 is selected from an integer of 1 to 4, and the e2 is selected from an integer of 1 to 3; The Rt is the same or different and is selected from one of hydrogen, deuterium, tritium, a cyano group, a halogen, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, and a substituted or unsubstituted phenyl group; The Z is the same or different and is selected from C(Rz) or N; and, at most one of the Z is selected from N; Rz is independently selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, a —Si(R k )3 group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted phenyl group, or two adjacent Rz are bonded to each other to form a substituted or unsubstituted: benzene ring, pyridine ring; in the case where Rz and Re are two or more, each of Rz and Re is the same or different; each R k is independently selected from the group consisting of a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group, a substituted or unsubstituted heptyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted cycloheptyl group; the "substituted" in the "substituted or unsubstituted phenyl group" is selected from the group consisting of deuterium, tritium, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tri-tert-butylsilyl; At least one of the Ar1, Ar2, Rz contains a group represented by Formula 1-b; and, the number of the group selected from Formula 1-b in Formula 1 is one or two; the Ra, Rb, Rc are independently selected from one of the following groups consisting of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane; except for "substituted or unsubstituted phenyl" in Rz, the "substitution" in "substituted or unsubstituted" represents a substituent selected from the following groups consisting of deuterium, tritium; but the silane-containing indolocarbazole compound of formula 1 excludes the structures shown in formula 1-b1 and formula 1-b2, 。 2. The silane-containing indolocarbazole compound according to claim 1, characterized by at least one of the Ar1, Ar2 is selected from one of the following groups consisting of 。 3. The silane-containing indolocarbazole compound according to claim 1, wherein the Ar1, Ar2 is not a group of formula 1-a selected from one of the following groups consisting of 。 4. The silane-containing indolocarbazole compound according to claim 1, characterized by the L, L1, L2 are independently selected from one of the following groups consisting of a single bond, one of the following groups consisting of 。 5. A silane-containing indolocarbazole compound characterized in that, the silane-containing indolocarbazole compound is selected from at least one of the following structures consisting of 。 6. An organic electroluminescent device, characterized by the organic electroluminescence device contains the silane-containing indolocarbazole compound according to any one of claims 1 to 5.

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