An organic compound and its application and an organic electroluminescent device containing the same

Abstract

The present invention relates to a novel organic compound having the following structure: a , R b , R c and R n Each is independently selected from hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; X 1 Selected from NR 1 , CR 2 R 3 、SiR 19 R 20 Any one of S and O; at least one hydrogen in the structure of formula (1) is deuterated. When the compound of the present invention is used as a light-emitting layer material in an OLED device, it exhibits excellent device performance and stability. The present invention also protects an organic electroluminescent device using the compound of the above general formula.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent materials, specifically to a novel organic compound, and in particular to a thermally activated delayed fluorescent material for an organic electroluminescent device and its application in the organic electroluminescent device. Background Art

[0002] Optoelectronic devices using organic materials are becoming increasingly popular for a number of reasons. Many of the materials used to make such devices are relatively cheap, and optoelectronic devices have potential cost advantages over inorganic devices. In the structure of organic electroluminescent devices in the display and lighting fields, blue fluorescence is generally used in combination with red and green phosphorescent materials. Recently, a literature has reported an ultra-pure blue fluorescent dye BN compound based on TADF (Thermally Activated Delayed Fluorescence). This type of compound is based on triphenylboron and contains two nitrogen atoms, forming a rigid polycyclic aromatic skeleton. The nitrogen atom has an opposite resonance effect to the boron atom, and the opposite resonance effect is enhanced at its para position. Therefore, this effect can clearly separate the HOMO and LUMO orbitals. The calculated molecular orbitals of DABNA-1 show that the LUMO orbital is distributed on the boron atom and the ortho and para positions of the boron atom, and the HOMO orbital is distributed on the nitrogen atom and the meta position of the boron atom.

[0003]

[0004] BN compounds, based on triphenylborane, contain two nitrogen atoms, forming a rigid polycyclic aromatic skeleton. The nitrogen atom has an opposite resonance effect to the boron atom, and the opposite resonance effect is enhanced in its para position. Therefore, this effect can clearly separate the HOMO and LUMO orbitals. Summary of the invention

[0005] In order to solve the above technical problems, the present invention provides a new type of compound, specifically a thermally activated delayed fluorescence material that can be used in an organic electroluminescent device, and also provides the application of the compound in an organic electroluminescent device.

[0006] The novel compound of the present invention has a structure represented by the general formula (1):

[0007]

[0008] In formula (1): R a , R b , R c and R nEach independently represents a single substituent to the maximum permissible substituent, and is independently selected from one of hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silane, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

[0009] X 1 Selected from NR 1 , CR 2 R 3 、SiR 19 R 20 , S and O, R 1 , R 2 , R 3 , R 19 and R 20 are each independently selected from one of hydrogen, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; and when the X 1 NR 1 When R 1 With Ring 1 and / or R a Connected into a ring or not connected into a ring;

[0010] Furthermore, at least one hydrogen atom in the compound structure represented by formula (1) is deuterated.

[0011] When the above-mentioned substituted or unsubstituted groups have substituents, the substituents are selected from one or more of deuterium, halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, deuterated C3-C12 cycloalkyl, C1-C12 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aromatic or condensed aromatic, C3-C30 monocyclic heteroaryl or condensed heteroaryl.

[0012] More preferably, in the above formula (1), R a , R b and R c At least one of them is deuterium.

[0013] More preferably, in the above formula (1), R a , R b and R cAt least one of them is a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group.

[0014] More preferably, in the above formula (1), R n It is a substituted C6-C30 aryl group having at least one substituent group, or a substituted C3-C30 heteroaryl group having at least one substituent group, wherein the substituent group is selected from deuterium, deuterated C1-C12 chain alkyl or deuterated C3-C12 cycloalkyl.

[0015] Further preferably, in the above formula (1), when the X 1 NR 1 When R 1 is selected from substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C3~C 30 The substituent is selected from one of the following groups: deuterium, halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, deuterated C3-C12 cycloalkyl, C1-C12 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, or a combination of more thereof.

[0016] More preferably, in the above formula (1), when X 1 Selected from NR 1 When the R 1 is a substituted C6-C30 aryl group having at least one substituent group, or is a substituted C3-C 30 Heteroaryl, wherein the substituent group is selected from deuterium, deuterated C1-C12 chain alkyl or deuterated C3-C12 cycloalkyl;

[0017] Or when X 1 Selected from CR 2 R 3 When the R 2 or R 3 At least one of them is a substituted C6-C30 aryl group having at least one substituent group, or a substituted C3-C 30 Heteroaryl, wherein the substituent group is selected from deuterium, deuterated C1-C12 chain alkyl or deuterated C3-C12 cycloalkyl;

[0018] Or when X 1 Selected from SiR 19 R 20 When the R 19 or R 20At least one of them is a substituted C6-C30 aryl group having at least one substituent group, or a substituted C3-C 30 The heteroaryl group, wherein the substituent group is selected from deuterium, deuterated C1-C12 chain alkyl or deuterated C3-C12 cycloalkyl.

[0019] Further preferably, the compounds of the present invention have the following structural formulas (2-1) to (2-5):

[0020]

[0021] In formulas (2-1) to (2-5), R a , R b , R c , R n , R 1 , R 2 , R 3 , R 19 and R 20 The definition of is the same as that in formula (1), and at least one hydrogen in the structure of each compound represented by formulas (2-1) to (2-5) is deuterated;

[0022] Preferably, in formulas (2-1) to (2-5), R a , R b and R c At least one of them is deuterium;

[0023] Preferably, in formulas (2-1) to (2-5), R a , R b and R c At least one of them is a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group.

[0024] Still more preferably, the compounds of the present invention have the following structural formulas (3-1) and (3-2):

[0025]

[0026] In formula (3-1) or (3-2), R a , R b , R c , R n The definition of is the same as that in formula (1);

[0027] R d and R d’Each independently represents a single substituent to the maximum permissible substituent, and is independently selected from hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silane, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl. The substituent is selected from the group consisting of deuterium, halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, deuterated C3-C12 cycloalkyl, C1-C12 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl or condensed aryl, C3-C30 monocyclic heteroaryl or condensed heteroaryl, or a combination of more thereof;

[0028] and at least one hydrogen in each compound structure represented by formula (3-1) or (3-2) is deuterated;

[0029] Preferably, R d and R d’ Each is independently selected from one of hydrogen, deuterium, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, and deuterated C3-C12 cycloalkyl;

[0030] Preferably, in formula (3-1) or (3-2), R a , R b and R c At least one of them is deuterium;

[0031] Preferably, in formula (3-1) or (3-2), R a , R b and R c At least one of them is a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group.

[0032] More preferably, in the above formula (1), formula (2-1) to (2-5), formula (3-1) and (3-2), at least one R n is a nitrogen-containing substituted or unsubstituted C4-C30 electron-donating heteroaryl group;

[0033] More preferably, in the above formula (1), formula (2-1) to (2-5), formula (3-1) and (3-2), R n Only one of the groups is a nitrogen-containing substituted or unsubstituted C4-C30 electron-donating heteroaryl group.

[0034] More preferably, the compound of the present invention has the structural formula shown below (4):

[0035]

[0036] Among them, R n1 , R n2 and R n3 Each is independently selected from hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the above substituents are selected from deuterium, A combination of one or more of halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, deuterated C3-C12 cycloalkyl, C1-C12 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl or condensed aryl, C3-C30 monocyclic heteroaryl or condensed heteroaryl;

[0037] Preferably, the R n1 , R n2 and R n3 Only one of the following is a nitrogen-containing substituted or unsubstituted C4-C30 electron-donating heteroaryl group, wherein the substituent is selected from one or more of deuterium, halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, and deuterated C3-C12 cycloalkyl;

[0038] More preferably, the R n2 It is a nitrogen-containing substituted or unsubstituted C4-C30 electron-donating heteroaryl group, wherein the substituent is selected from one or a combination of deuterium, halogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, and deuterated C3-C12 cycloalkyl.

[0039] More preferably, in the above formula (1), formula (2-1) to (2-5), formula (3-1), (3-2), and formula (4) of the present invention, R a , R b and R c Each is independently selected from hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; more preferably, R a , R b and R c Each is independently selected from one of hydrogen, C1-C12 chain alkyl, and C3-C12 cycloalkyl.

[0040] More preferably, R in the above formula (1), formula (2-1) to (2-5), formula (3-1) and (3-2) of the present invention is n and R in formula (4) n1 , R n2 and R n3 Each independently selected from the following Hy 1 ~Hy 3 The structure:

[0041]

[0042] Among them, * indicates the connection site with the mother nucleus;

[0043] The Hy 1 In the formula, n is 0 or 1. When n=0, it indicates a single bond. 1 Selected from CR 4 R 5 NR 6 , O, S or SiR 13 R 14 One of;

[0044] The Hy 2 In, E 2 Selected from CR 7 R 8 NR 9 , O, S or SiR 15 R 16 One of;

[0045] The Hy 3 In, E 3 and E 4 Each independently selected from a single bond, CR 10 R 11 NR 12 , O, S or SiR 17 R 18 One of the above, and E 3 and E 4 At least one of the following is NR 12 ;

[0046] Hy 1 、Hy 2 or Hy 3 In, R e , R f , R h , R g , R i , R j and R kEach independently represents a single substituent to the maximum permissible substituent, and is independently selected from hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or R e , R f , R h , R g , R i , R j and R k Each independently and separately connected to the aromatic ring is fused to form a substituted or unsubstituted C9-C30 aryl group or a substituted or unsubstituted C9-C30 heteroaryl group; preferably, R e , R f , R g , R h , R i , R j and R k Each is independently selected from one of hydrogen, C1-C12 chain alkyl, and C3-C12 cycloalkyl;

[0047] The substituted or unsubstituted C9-C30 aryl or substituted or unsubstituted C9-C30 heteroaryl may specifically include: the C9-C30 aryl or heteroaryl may be optionally substituted by 0-5 of the following groups independently: a substituted or unsubstituted C1-C12 chain alkyl, a C3-C12 cycloalkyl, a halogen, a C1-C6 alkoxy or thioalkoxy, a C6-C30 monocyclic aromatic hydrocarbon or condensed aromatic hydrocarbon group, a C3-C30 monocyclic heteroaromatic hydrocarbon or condensed heteroaromatic hydrocarbon group.

[0048] Hy 1 、Hy 2 or Hy 3 In the R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18Each is independently selected from hydrogen, C1-C12 chain alkyl, C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; preferably, R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Each is independently selected from a C1-C12 chain alkyl group, a C3-C12 cycloalkyl group, and a substituted or unsubstituted C6-C30 aryl group.

[0049] More preferably, R in the above formula (1), formula (2-1) to (2-5), formula (3-1) and (3-2) of the present invention is n and R in formula (4) n1 , R n2 and R n3 Each independently has at least one selected from the following (Hy 1 -1)-(Hy 3 -6) in any of the following structures:

[0050]

[0051] The R e , R f , R h , R i , R g , R j , R k , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Independently with 1 、Hy 2 or Hy 3 The same definition as in .

[0052] More preferably, R in the above formula (1), formula (2-1) to (2-5), formula (3-1) and (3-2) of the present invention is n and R in formula (4) n1 , R n2 and R n3 Each independently has at least one selected from the following groups (Hy 1 -1)-(Hy 3 -6) Any one of:

[0053]

[0054] The R e , R f , R h , R g , R i , R j , R k , R 7 , R 8 , R 9 , R 15 , R 16 , R 10 , R 11 , R 12 , R 17 and R 18 Independently and in Hy 1 、Hy 2 or Hy 3 The same definition as in .

[0055] More preferably, the above R of the present invention 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R a , R b , R c , R d , R e , R f , R g , R h , R i , R j and Rk When selected from C1-C12 chain alkyl or C3-C12 cycloalkyl, selected from the following structures:

[0056]

[0057] It should be noted that, in the present invention, the maximum permissible substituent refers to the maximum number of substituents under the premise that the substituted group meets the requirements of the chemical bond. For example, the R a The number of can be one or more, but can only reach the maximum allowed substituents (i.e. 4).

[0058] In the present specification, the expression of Ca to Cb represents that the number of carbon atoms in the group is a to b. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

[0059] In the present specification, the expression of a ring structure crossed by “—” indicates that the connection site is any position on the ring structure that can form a bond.

[0060] In the present specification, the substituted or unsubstituted C6-C30 aryl group is preferably a C6-C20 aryl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, an indenyl group, a fluorenyl group and its derivatives, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a peryl group, A group consisting of a tetraphenyl group and a naphthyl group. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes 1-naphthyl and 2-naphthyl; the anthracenyl group is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from 9,9'-dimethylfluorene, 9,9'-spirobifluorene and benzofluorene; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetraphenyl group is selected from 1-tetraphenyl, 2-tetraphenyl and 9-tetraphenyl.

[0061] The heteroatom in the present invention generally refers to an atom or an atom group selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0062] In the present specification, the substituted or unsubstituted C3~C30 heteroaryl group is preferably a C4~C20 heteroaryl group, and more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, etc. Specific examples include: furyl, thienyl, pyrrolyl, benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazole and derivatives thereof, wherein the carbazole derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole, benzocarbazole, dibenzocarbazole, or indolecarbazole.

[0063] In the present specification, the C1-C20 chain alkyl group is preferably a C1-C10 chain alkyl group, and more preferably a C1-C6 chain alkyl group, examples of which include methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, and tert-butyl.

[0064] In the present specification, the C3-C12 cycloalkyl group includes a monocyclic alkyl group and a polycyclic alkyl group, and preferably a C1-C10 alkyl group and a C3-C10 cycloalkyl group.

[0065] Furthermore, the compound of the general formula (1) of the present invention can preferably be one of the following specific structural compounds:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] The C1~C10 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.

[0074] The C1~C6 can be C1, C2, C3, C4, C5, C6, etc.

[0075] The C3~C10 can be C3, C4, C5, C6, C7, C8, C9, C10, etc.

[0076] The C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, etc., preferably C1-C10.

[0077] The value ranges of C1-C10, C1-C6, C3-C10, and C1-C12 involved subsequently in the present invention are the same as the above-mentioned value ranges.

[0078] In the present invention, R n1 , R n2 and R n3 Only one of them is a nitrogen-containing electron-donating heteroaryl group, preferably R n2 is a nitrogen-containing electron-donating heteroaryl because R n2 The steric repulsion with the groups on both sides is minimal, making it more stable.

[0079] In the present invention, R n1 , R n2 and R n3 At least one of the nitrogen-containing electron-donating heteroaryl groups is selected from a specific type, which has a higher conjugation strength than other electron-donating heteroaryl groups, can effectively increase the LUMO orbital energy level of the compound, and can effectively reduce the direct injection of electrons.

[0080] The invention also discloses a thermally activated delayed fluorescent material, which contains the compound as mentioned above.

[0081] The present invention also discloses an application of the thermally activated delayed fluorescent material as described above in an organic electroluminescent device, preferably as a light-emitting layer in the organic electroluminescent device, and more preferably as a light-emitting dye and / or sensitizer in the light-emitting layer of the organic electroluminescent device.

[0082] The above-mentioned compounds of the present invention have thermally activated delayed fluorescence properties.

[0083] The present invention also discloses an application of the above compound in an organic electroluminescent device. The above compound of the present invention is suitable for use as a light-emitting layer material in an organic electroluminescent device, and more preferably used as a light-emitting dye and / or sensitizer in the light-emitting layer of the organic electroluminescent device.

[0084] The application fields of the compounds of the present invention are not limited to organic electroluminescent materials, but can also be applied to optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners and other large-area sensors, electronic paper and other technical fields.

[0085] The present invention also provides an organic electroluminescent device, comprising a substrate, a first electrode, a second electrode and one or more organic layers inserted between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by any one of the above general formula (1), formulas (2-1) to (2-5), formula (3-1), (3-2) and formula (4).

[0086] Specifically, one embodiment of the present invention provides an organic electroluminescent device, comprising a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a light-emitting layer is provided between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains a compound of the present invention represented by any one of the above formulas (1), (2-1) to (2-5), (3-1), (3-2) and (4).

[0087] The specific reason why the above-mentioned compounds of the present invention have excellent performance as light-emitting layer materials in organic electroluminescent devices is still unclear, but it is speculated that the reasons may be as follows:

[0088] 1. The boron atom contained in the molecular structure of the compound of the present invention has a resonance effect with the nitrogen atom in the same ring, and the opposite resonance effect will be enhanced at the para position. Therefore, this effect can obviously separate the HOMO and LUMO orbits of the molecule, and the compound thus has the property of thermally activated delayed fluorescence;

[0089] 2. The introduction of a rigid carbazole group into the molecular structure of the compound of the present invention helps to adjust the charge distribution of the compound, which is beneficial to further delocalize the electrons, thereby increasing the fluorescence quantum yield of the compound and facilitating its use as a dye;

[0090] 3. At least one hydrogen atom in the molecular structure of the compound of the present invention is replaced by deuterium, which helps to improve the life of the device after being applied to the organic electroluminescent device;

[0091] 4. Compared with devices prepared using compounds of the present invention as luminescent dyes, organic electroluminescent devices using compounds of the present invention have relatively lower voltage, relatively higher efficiency and lifespan, showing excellent device performance. DETAILED DESCRIPTION

[0092] The specific preparation methods of the above-mentioned novel compounds of the present invention are described in detail below using multiple synthesis examples as examples, but the preparation methods of the present invention are not limited to these synthesis examples. The acquisition of the compound is not limited to the synthesis method and raw materials used in the present invention, and those skilled in the art can also select other methods or routes to obtain the novel compounds proposed in the present invention. The compounds not mentioned in the present invention are raw materials obtained from commercial channels, or are prepared by themselves according to known methods using these raw materials.

[0093] The solvents and reagents used in the synthesis examples, such as dichloromethane, petroleum ether, ethanol, tetrahydrofuran, N,N-dimethylacetamide, anhydrous magnesium sulfate, carbazole and other chemical reagents, can be purchased from the domestic chemical product market, such as Sinopharm Group Reagent Company, TCI Company, Shanghai Bid Pharmaceutical Company, Bailingwei Reagent Company, etc. In addition, those skilled in the art can also synthesize by known methods.

[0094] The analysis and detection of the intermediates and compounds in the synthesis examples were performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0095] The synthesis method of the compound of the present invention is briefly described below.

[0096] Synthesis Example

[0097] Representative synthetic routes:

[0098]

[0099] More specifically, the synthesis methods of representative compounds of the present invention are given below.

[0100] Synthesis Example

[0101] Synthesis Example 1: Synthesis of S5

[0102]

[0103] Synthesis of intermediate S5-1:

[0104] 3,5-dibromofluorobenzene (50g, 197mmol), 3,6-di-tert-butylcarbazole (66.1g, 236mmol), cesium carbonate (56.9g, 295mmol), DMF (500ml) were added to a 1L single-mouth bottle at room temperature, and the mixture was reacted at 120°C overnight. The heating was stopped, and 500ml of water was added after cooling to room temperature, and the mixture was extracted with 500ml of dichloromethane, dried with anhydrous sodium sulfate, and subjected to silica gel column chromatography (PE) to obtain 99.50g of a white solid product with a yield of 98%. The molecular ion mass determined by mass spectrometry was 512.33 (theoretical value: 513.32).

[0105] Synthesis of intermediate S5-2:

[0106] At room temperature, S5-1 (50 g, 83.1 mmol), 4,5-deuterated carbazole (15.47 g, 91.4 mmol), Pd2(dba)3 (7.61 g, 8.3 mmol), tri-tert-butylphosphine (3.94 g, 19.5 mmol), sodium tert-butoxide (18.72 g, 194.8 mmol), and xylene (500 ml) were added to a 1L single-mouth bottle, and nitrogen was pumped three times, and heated to 130°C for overnight reaction. The reaction solution was cooled to room temperature, filtered, and the filtrate was concentrated by mixing with silica gel. 60 g of crude product was obtained by column chromatography (PE: EA = 100: 1), and 50 g of white solid was obtained by recrystallization from toluene / ethanol, with a yield of 85%. The molecular ion mass determined by mass spectrometry was 602.63 (theoretical value: 601.63).

[0107] Synthesis of intermediate S5-3:

[0108] At room temperature, S5-2 (50 g, 97.4 mmol), diphenylamine (18.13 g, 107.1 mmol), Pd2(dba)3 (8.92 g, 9.7 mmol), tri-tert-butylphosphine (3.36 g, 16.6 mmol), sodium tert-butoxide (15.97 g, 166.2 mmol), and xylene (500 ml) were added to a 1 L single-mouth bottle, and nitrogen was pumped three times, and heated to 130 ° C to react overnight. The reaction solution was cooled to room temperature, filtered, and the filtrate was mixed with silica gel and concentrated. 60 g of crude product was obtained by column chromatography (PE: EA = 100: 1), and 47 g of white solid was obtained by recrystallization from toluene / ethanol, with a yield of 82%. The molecular ion mass determined by mass spectrometry was 689.93 (theoretical value: 689.94).

[0109] Synthesis of compound S5:

[0110] S5-3 (20.00 g, 28.9 mmol) was added to a 1000 ml three-necked flask, and o-dichlorobenzene (200 ml) and N, N-diisopropylethylamine (7.49 g, 57.9 mmol) were added. The flask was filled with nitrogen three times. Boron tribromide (36.31 g, 144.9 mol) was quickly extracted with a thick needle and added to the three-necked flask. The heating jacket was heated to reflux and the reflux reaction was carried out for 3 hours. After the system was cooled to room temperature, water (200 ml) was added to quench the system. When the system was no longer smoking, the quenching was completed. Liquid separation, the lower organic phase was taken, the aqueous phase was extracted three times with ethyl acetate (200 ml), the organic phases were combined, and dried over anhydrous sodium sulfate. The organic phase was mixed with silica gel and concentrated, and 10 g of crude product was obtained by column chromatography. 7 g of yellow solid was obtained by recrystallization from toluene / ethanol, with a yield of 34%. The molecular ion mass determined by mass spectrometry was 697.01 (theoretical value: 697.73).

[0111] Synthesis Example 2: Synthesis of S25

[0112]

[0113] Synthesis of intermediate S25-1:

[0114] At room temperature, S5-2 (40 g, 66.5 mmol), diphenylamine (12.23 g, 73.1 mmol), Pd2(dba)3 (6.09 g, 6.6 mmol), tri-tert-butylphosphine (2.69 g, 13.3 mmol), sodium tert-butoxide (12.78 g, 166.232.9 mmol), and xylene (500 ml) were added to a 1 L single-mouth bottle, and nitrogen was pumped three times, and heated to 130 ° C to react overnight. The reaction solution was cooled to room temperature, filtered, and the filtrate was mixed with silica gel and concentrated. Column chromatography (PE: EA = 100: 1) obtained 50 g of crude product, and toluene / ethanol recrystallization obtained 39 g of white solid, with a yield of 85%. The molecular ion mass determined by mass spectrometry was: 688.93 (theoretical value: 687.93).

[0115] Synthesis of compound S25:

[0116] S25-1 (20.00 g, 29.1 mmol) was added to a 1000 ml three-necked flask, and o-dichlorobenzene (200 ml) and N, N-diisopropylethylamine (7.52 g, 58.1 mmol) were added. The flask was filled with nitrogen three times. Boron tribromide (36.42 g, 145.3 mol) was quickly extracted with a thick needle and added to the three-necked flask. The heating jacket was heated to reflux and the reflux reaction was carried out for 3 hours. After the system was cooled to room temperature, water (200 ml) was added to quench the system. When the system was no longer smoking, the quenching was completed. Liquid separation was performed, the lower organic phase was taken, the aqueous phase was extracted three times with ethyl acetate (200 ml), the organic phases were combined, and dried over anhydrous sodium sulfate. The organic phase was mixed with silica gel and concentrated, and 12 g of crude product was obtained by column chromatography. 8 g of yellow solid was obtained by recrystallization from toluene / ethanol, with a yield of 40%. The molecular ion mass determined by mass spectrometry was 695.76 (theoretical value: 695.71).

[0117] Synthesis Example 3: Synthesis of S45

[0118]

[0119] Synthesis of intermediate S45-1:

[0120] At room temperature, add 2-chloro-3-isophenylpropyl-5-fluorobromobenzene (50g, 152.6mmol), 3,6-di-tert-butylcarbazole (51.17g, 183.1mmol), cesium carbonate (44.2g, 228.9mmol), DMF (500ml) to a 1L single-mouth bottle, and react at 120℃ overnight. Stop heating, add 500ml of water after cooling to room temperature, extract with 500ml of dichloromethane, dry with anhydrous sodium sulfate, and silica gel column chromatography (PE) to obtain 81g of white solid product with a yield of 90%. The molecular ion mass determined by mass spectrometry is: 586.05 (theoretical value: 587.04).

[0121] Synthesis of intermediate S45-2:

[0122] At room temperature, S45-1 (80 g, 66.5 mmol), 4,5-dideuterocarbazole (25.37 g, 149.9 mmol), Pd2(dba)3 (12.48 g, 13.63 mmol), tri-tert-butylphosphine (5.51 g, 27.3 mmol), sodium tert-butoxide (26.19 g, 272.5 mmol), and xylene (1000 ml) were added to a 2L single-mouth bottle, and nitrogen was pumped three times, and heated to 130°C for overnight reaction. The reaction solution was cooled to room temperature, filtered, and the filtrate was concentrated by mixing with silica gel. Column chromatography (PE: EA = 100: 1) obtained 89 g of crude product, and toluene / ethanol recrystallization obtained 77 g of white solid, with a yield of 84%. The molecular ion mass determined by mass spectrometry was 675.94 (theoretical value: 675.35).

[0123] Synthesis of compound S45:

[0124] S45-2 (20.00 g, 29.6 mmol) was added to a 1000 ml three-necked flask, and o-xylene (300 ml) was added. The flask was filled with nitrogen three times. In an ice-water bath, n-butyl lithium solution (21 ml, 1.6 M, 33 mmol) was added dropwise to the three-necked flask with a thick needle. The mixture was stirred for 1 hour. Boron tribromide (8.16 g, 32.5 mmol) was extracted with a thick needle in an ice-water bath and added to the reaction solution. The mixture was stirred for 30 minutes, heated to 45 ° C and stirred for 50 minutes. In an ice-water bath, N, N-diisopropylethylamine (7.6 g, 59.2 mmol) was extracted and added to the reaction system. The mixture was stirred for 30 minutes, heated to 120 ° C, and reacted overnight. The heating was stopped, and water (500 ml) was added to quench the mixture after the system cooled to room temperature. The lower organic phase was separated, and the aqueous phase was extracted three times with ethyl acetate (500 ml). The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was mixed with silica gel and concentrated, and 8 g of crude product was obtained by column chromatography, and 5 g of yellow solid was obtained by recrystallization from toluene / ethanol, with a yield of 26%. The molecular ion mass determined by mass spectrometry was 648.73 (theoretical value: 648.71).

[0125] Synthesis Example 4: Synthesis of S65

[0126]

[0127] Synthesis of intermediate S65-1:

[0128] Add 3,5-difluoro-2-chlorobromobenzene (50g, 220mmol), 3,6-di-tert-butylcarbazole (61.4g, 220mmol), cesium carbonate (107.4g, 330mmol), DMF (500ml) to a 1L single-mouth bottle at room temperature, and react at 120°C overnight. Stop heating, add 500ml of water after cooling to room temperature, extract with 500ml of dichloromethane, dry with anhydrous sodium sulfate, and mix with silica gel column chromatography (PE) to obtain 90g of white solid product with a yield of 90%. The molecular ion mass determined by mass spectrometry is 453.40 (theoretical value: 452.41).

[0129] Synthesis of intermediate S65-2:

[0130] At room temperature, S65-1 (90 g, 199 mmol), 4,5-dideuterocarbazole (37.03 g, 219 mmol), Pd2(dba)3 (18.22 g, 19.89 mmol), tri-tert-butylphosphine (8.05 g, 39.79 mmol), sodium tert-butoxide (38.24 g, 398 mmol), and xylene (1000 ml) were added to a 2L single-mouth bottle, and nitrogen was pumped three times, and heated to 130°C for overnight reaction. The reaction solution was cooled to room temperature, filtered, and the filtrate was concentrated by mixing with silica gel. Column chromatography (PE: EA = 100: 1) obtained 110 g of crude product, and toluene / ethanol recrystallization obtained 94 g of white solid, with a yield of 82%. The molecular ion mass determined by mass spectrometry was: 575.17 (theoretical value: 575.16).

[0131] Synthesis of intermediate S65-3:

[0132] S65-2 (95 g, 156 mmol), phenol (16.2 g, 172 mmol), potassium carbonate (32.44 g, 235 mmol), DMF (1000 ml) were added to a 2 L single-mouth bottle at room temperature, and the mixture was reacted at 120°C overnight. The heating was stopped, and 500 ml of water was added after cooling to room temperature, and the mixture was extracted with 500 ml of dichloromethane, dried over anhydrous sodium sulfate, and subjected to silica gel column chromatography (PE) to obtain 86 g of a white solid product with a yield of 85%. The molecular ion mass determined by mass spectrometry was 649.26 (theoretical value: 649.27).

[0133] Synthesis of compound S65:

[0134] S65-3 (20.00 g, 30.8 mmol) was added to a 1000 ml three-necked flask, and o-xylene (300 ml) was added. The flask was filled with nitrogen three times. In an ice-water bath, n-butyl lithium solution (21 ml, 1.6 M, 33 mmol) was added dropwise to the three-necked flask with a thick needle. The mixture was stirred for 1 hour. Boron tribromide (8.16 g, 32.5 mmol) was extracted with a thick needle in an ice-water bath and added to the reaction solution. The mixture was stirred for 30 minutes, heated to 45 ° C and stirred for 50 minutes. In an ice-water bath, N, N-diisopropylethylamine (7.96 g, 61.6 mmol) was extracted and added to the reaction system. The mixture was stirred for 30 minutes, heated to 120 ° C, and reacted overnight. The heating was stopped, and water (500 ml) was added to quench the mixture after the system cooled to room temperature. The lower organic phase was separated, and the aqueous phase was extracted three times with ethyl acetate (500 ml). The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was mixed with silica gel and concentrated, and 9 g of crude product was obtained by column chromatography, and 5.5 g of yellow solid was obtained by recrystallization from toluene / ethanol, with a yield of 28%. The molecular ion mass determined by mass spectrometry was 623.41 (theoretical value: 622.62).

[0135] Synthesis Example 4: Synthesis of S85

[0136]

[0137] Synthesis of intermediate S85-1:

[0138] Add phenyl-3-bromo-2-chloro-5-fluorophenyl sulfide (50g, 157mmol), 3,6-di-tert-butylcarbazole (48.3g, 173mmol), cesium carbonate (76.9g, 236mmol), DMF (500ml) to a 1L single-mouth bottle at room temperature, and react at 120°C overnight. Stop heating, add 500ml of water after cooling to room temperature, extract with 500ml of dichloromethane, dry with anhydrous sodium sulfate, and mix with silica gel column chromatography (PE) to obtain 80g of white solid product with a yield of 94%. The molecular ion mass determined by mass spectrometry is 542.59 (theoretical value: 542.58).

[0139] Synthesis of intermediate S85-2:

[0140] At room temperature, S85-1 (80 g, 147 mmol), 3,6-dideuterocarbazole (27.45 g, 162 mmol), Pd2(dba)3 (13.47 g, 14.71 mmol), tri-tert-butylphosphine (5.97 g, 29.49 mmol), sodium tert-butoxide (38.24 g, 398 mmol), and xylene (1000 ml) were added to a 2L single-mouth bottle, and nitrogen was pumped three times, and heated to 130°C for overnight reaction. The reaction solution was cooled to room temperature, filtered, and the filtrate was concentrated by mixing with silica gel. Column chromatography (PE: EA = 100: 1) obtained 100 g of crude product, and toluene / ethanol recrystallization obtained 83 g of white solid, with a yield of 85%. The molecular ion mass determined by mass spectrometry was 665.32 (theoretical value: 665.33).

[0141] Synthesis of compound S85:

[0142] S85-2 (20.49 g, 30.8 mmol) was added to a 1000 ml three-necked flask, and o-xylene (300 ml) was added. The flask was filled with nitrogen three times. In an ice-water bath, n-butyl lithium solution (21 ml, 1.6 M, 33 mmol) was added dropwise to the three-necked flask with a thick needle. The mixture was stirred for 1 hour. Boron tribromide (8.16 g, 32.5 mmol) was extracted with a thick needle in an ice-water bath and added to the reaction solution. The mixture was stirred for 30 minutes, heated to 45 ° C and stirred for 50 minutes. In an ice-water bath, N, N-diisopropylethylamine (7.96 g, 61.6 mmol) was extracted and added to the reaction system. The mixture was stirred for 30 minutes, heated to 120 ° C, and reacted overnight. The heating was stopped, and water (500 ml) was added to quench the mixture after the system cooled to room temperature. The lower organic phase was separated, and the aqueous phase was extracted three times with ethyl acetate (500 ml). The organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was mixed with silica gel and concentrated, and 11 g of crude product was obtained by column chromatography, and 6.2 g of yellow solid was obtained by recrystallization from toluene / ethanol, with a yield of 31%. The molecular ion mass determined by mass spectrometry was 638.69 (theoretical value: 638.68).

[0143] Next, the application of the compound of the present invention and the organic electroluminescent device prepared by using the compound of the present invention are described in detail.

[0144] The embodiment of the present invention also provides an organic electronic light-emitting device comprising the above-mentioned compound of the present invention. OLED is used as an organic electronic light-emitting device as an example of a device for illustration below, but it should be understood that the following detailed description is not a limitation of the present invention, and those skilled in the art can extend the following detailed description to other organic electronic light-emitting devices.

[0145] In an embodiment, the OLED includes a first electrode and a second electrode, and a plurality of organic material layers between the electrodes. The organic material layer can be divided into a plurality of regions. For example, the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.

[0146] In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may also be provided on the substrate used as a display.

[0147] The first electrode can be formed by sputtering or depositing the material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof can be used. When the first electrode is used as a cathode, a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof can be used.

[0148] The organic material layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc. The compound used as the organic material layer can be organic small molecules, organic macromolecules and polymers, and combinations thereof.

[0149] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a hole transport layer (HTL) of a single-layer structure, including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. The hole transport region can also be a multi-layer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).

[0150] The material of the hole transport region can be selected from, but not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives such as the compounds shown in HT-1 to HT-34 below; or any combination thereof.

[0151]

[0152]

[0153]

[0154] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can use one or more compounds of HT-1 to HT-34, or one or more compounds of HI-1 to HI-3 described below; or one or more compounds of HT-1 to HT-34 can be doped with one or more compounds of HI-1 to HI-3 described below.

[0155]

[0156] The light-emitting layer includes a light-emitting dye (i.e., a dopant) that can emit different wavelength spectra, and can also include a host material (Host). In one aspect of the present invention, the light-emitting layer adopts fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer can be selected from, but not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0157]

[0158]

[0159] The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an electron transport layer (ETL) of a single-layer structure, including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing multiple compounds. The electron transport region may also be a multilayer structure including at least one layer of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0160] In a specific example, the electron transport layer material can be selected from but not limited to one or more combinations of ET-1 to ET-57 listed below.

[0161]

[0162]

[0163]

[0164] In the example, the device may further include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes but is not limited to a combination of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li and / or Ca.

[0165] Device Example 1

[0166] In Example 1, the device structure is as follows:

[0167] ITO (150nm) / HI-2 (10nm) / HT-4 (40nm) / BFH-3:S5 (30nm, 5%wt) / ET-46:ET-57 (50%wt:50%wt) (25nm) / LiF (0.5nm) / Al (150nm). The organic electroluminescent device preparation process is as follows: a glass plate coated with a transparent conductive layer of ITO (thickness 150nm) is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol, baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam;

[0168] Place the glass substrate with the anode in a vacuum chamber and evacuate the chamber to a vacuum of less than 1×10 -5 Pa, HI-2 and HT-4 were vacuum evaporated on the above anode layer as hole injection layer and hole transport layer, respectively, with an evaporation rate of 0.1 nm / s and an evaporation film thickness of 10 nm and 40 nm, respectively;

[0169] "BFH-3: S5 (30nm, 5%wt)" was vacuum-deposited on the hole transport layer as the light-emitting layer of the organic electroluminescent device. The deposition rate was 0.1nm / s and the total deposition film thickness was 30nm. "5%wt" refers to the doping ratio of the blue light dye, that is, the weight ratio of the main material to the compound S5 of the present invention is 95:5.

[0170] Vacuum evaporation of ET-46:ET-57 (50% wt:50% wt) on the light-emitting layer as the electron transport layer of the organic electroluminescent device, with an evaporation rate of 0.1 nm / s and a total evaporation film thickness of 25 nm;

[0171] 0.5 nm of LiF as an electron injection layer and 150 nm of Al as a cathode were vacuum-deposited on the electron transport layer.

[0172] The manufacturing process of device examples 2-5 and comparative examples 1-2 is the same as that of device example 1, except that the dye S5 is replaced by compounds S25, S45, S65, S85 of the present invention and compounds R-1 and R-2 in the prior art, respectively. The structures of R-1 and R-2 are shown below:

[0173]

[0174] The organic electroluminescent device prepared by the above process was subjected to the following performance tests:

[0175] At the same brightness, the driving voltage and current efficiency of the organic electroluminescent devices prepared in Examples 1-5 and Comparative Examples 1-2, as well as the device life, were measured using a digital source meter and a brightness meter. Specifically, the voltage was increased at a rate of 0.1 V per second, and the brightness of the organic electroluminescent device was measured when it reached 1000 cd / m 2 The voltage at which the light is on is the driving voltage, and the current density at this time is measured at the same time; the ratio of brightness to current density is the current efficiency; the life test of LT95 is as follows: use a brightness meter at 1000cd / m 2 At the same brightness, the current is kept constant and the brightness of the organic electroluminescent device is measured to drop to 950cd / m 2 The time in hours.

[0176] The specific performance data of the organic electroluminescent devices prepared in the above-mentioned embodiments of the present invention are shown in Table 1 below, wherein the lifespan value of Comparative Example 1 is taken as Standard 1, and the lifespan values ​​in other embodiments are ratios thereof.

[0177] Table 1

[0178]

[0179] As can be seen from Table 1 above, when the compound of the present invention is used as the dye in the light-emitting layer, the voltage is reduced, the efficiency and life are improved compared with the comparative example compound, showing excellent device performance. This is because the compound of the present invention increases the molecular rigidity, improves its luminous efficiency, and increases the degree of molecular conjugation. In addition, replacing hydrogen in the molecule with deuterium improves the stability of the material and improves the device life.

[0180] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above description is only a specific embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

[0181] Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the invention.

Claims

1. A compound of the general formula, as shown in the following formula (1): in: R a , R b , R c and R n Each independently represents a single substituent up to the maximum permissible substituent, R a , R b , R c Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl; R a , R b and R c At least one of them is deuterium; R n Each independently selected from the following Hy 1 The structure: Among them, * indicates the connection site with the mother nucleus; Formula Hy 1 In the formula, n is 0. When n=0, it indicates a single bond. Hy 1 In, R e , R f Each independently represents a single substituent to the maximum permissible substituent, and each independently is selected from one of hydrogen, C1-C12 chain alkyl, and C3-C12 cycloalkyl; X 1 Selected from NR 1 , CR 2 R 3 , S and O, R 1 is selected from substituted or unsubstituted C6-C30 aryl groups; R 2 , R 3 are independently selected from a substituted or unsubstituted C1-C12 chain alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C6-C30 aryl; and when the X 1 NR 1 When R 1 With Ring 1 and / or R b Connected into a ring or not connected into a ring; Furthermore, at least one hydrogen in the compound structure represented by formula (1) is deuterated; When the above-mentioned substituted or unsubstituted groups have a substituent, the substituent is selected from one of deuterium, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, and deuterated C3-C12 cycloalkyl; And is not the following compound:

2. The compound according to claim 1, wherein in the formula (1), R a , R b and R c At least one of them is a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group.

3. The compound according to claim 1, wherein in the formula (1): When X 1 Selected from NR 1 When the R 1 is a substituted C6-C30 aryl group having at least one substituent group selected from deuterium, a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group; Or when X 1 Selected from CR 2 R 3 When the R 2 or R 3 At least one of them is a substituted C6-C30 aryl group having at least one substituent group selected from deuterium, a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group.

4. The compound according to claim 1, as shown in the following formulas (2-1) to (2-4): In formulas (2-1) to (2-4), R a , R b , R c , R n , R 1 , R 2 , R 3 The definition of is the same as that in formula (1), and at least one hydrogen in each of the compound structures represented by formulae (2-1) to (2-4) is deuterated.

5. The compound according to claim 1, as shown in the following formula (3-1) or (3-2): In formula (3-1) or (3-2), R a , R b , R c , R n The definition of is the same as that in formula (1); R d and R d’ Each independently represents a single substituent to the maximum permissible substituent, and each independently is selected from one of hydrogen, deuterium, C1-C12 chain alkyl, C3-C12 cycloalkyl, deuterated C1-C12 chain alkyl, and deuterated C3-C12 cycloalkyl; Furthermore, at least one hydrogen in each compound structure represented by formula (3-1) or (3-2) is deuterated.

6. The compound according to claim 5, wherein in formula (3-1) or (3-2), R a , R b and R c At least one of them is a deuterated C1-C12 chain alkyl group or a deuterated C3-C12 cycloalkyl group.

7. The compound according to claim 1, as shown in the following formula (4): in, R n1 , R n2 and R n3 Each independently selected from the following Hy 1 The structure: Among them, * indicates the connection site with the mother nucleus; Formula Hy 1 In the formula, n is 0. When n=0, it indicates a single bond. Hy 1 In, R e , R f Each independently represents a monosubstituent, and each independently is selected from one of hydrogen, C1-C12 chain alkyl, and C3-C12 cycloalkyl.

8. The compound according to any one of claims 1, 4, 5 or 7, wherein in the formula (1), formula (2-1) to (2-4), formula (3-1), (3-2) or formula (4), R a , R b and R c Each is independently selected from one of hydrogen, C1-C12 chain alkyl, and C3-C12 cycloalkyl.

9. The compound according to claim 1, wherein R e , R f When selected from C1-C12 chain alkyl or C3-C12 cycloalkyl, it is selected from the following structures:

10. The compound according to claim 1, selected from the following structural compounds:

11. Use of the compound according to any one of claims 1 to 10 as a light-emitting layer material in an organic electroluminescent device. 12 . Use of the compound according to claim 11 as a luminescent dye and / or a sensitizer in a light-emitting layer of an organic electroluminescent device.

13. An organic electroluminescent device, comprising an anode layer, a plurality of light-emitting functional layers and a cathode layer; the plurality of light-emitting functional layers comprise at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and an electron transport layer formed in sequence, the hole injection layer is formed on the anode layer, and the cathode layer is formed on the electron transport layer; wherein, The light-emitting layer contains the organic compound according to any one of claims 1 to 10.

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