CN110746344A - Compound and application thereof - Google Patents

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CN110746344A
CN110746344A CN201911136445.1A CN201911136445A CN110746344A CN 110746344 A CN110746344 A CN 110746344A CN 201911136445 A CN201911136445 A CN 201911136445A CN 110746344 A CN110746344 A CN 110746344A
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肖文静
高威
代文朋
张磊
牛晶华
高优
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Wuhan Tianma Microelectronics Co Ltd
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Shanghai Tianma AM OLED Co Ltd
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Abstract

The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I or a formula II, can increase the solubility of the compound, provides great convenience for the synthesis, purification, evaporation and cleaning of the baffle plate of the molecule, is favorable for reducing the sublimation temperature of the molecule, it is also extremely advantageous for the device fabrication process, and, since the conjugated structure is interrupted from the middle, can improve the triplet state energy level of the compound, in addition, both ends of the flexible carbon chain X contain an electron-donating unit and an electron-withdrawing unit, can realize dual-core emission and improve the luminous efficiency of luminous molecules, moreover, each luminous core of the structure is provided with a D-A connecting element, the push-pull electronic structure increases the carrier transmission rate, thereby reducing the driving voltage of the device during operation.

Description

Compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
An organic light-Emitting Diode (OLED), also known as an organic electroluminescent display or an organic light-Emitting semiconductor, belongs to a current-type organic light-Emitting device, and is a phenomenon of light emission caused by injection and recombination of carriers, and the light emission intensity is proportional to the injected current. Under the action of an electric field, holes generated by an anode and electrons generated by a cathode move, are respectively injected into a hole transport layer and an electron transport layer, and migrate to a light emitting layer. When the two meet at the light emitting layer, energy excitons are generated, thereby exciting the light emitting molecules to finally generate visible light.
Materials that can be used for the light emitting layer of the OLED mainly include fluorescent materials, phosphorescent materials, triplet-triplet annihilation (TTA) materials, and Thermally Activated Delayed Fluorescence (TADF) materials according to a light emitting mechanism.
Wherein the singlet excited state S of the fluorescent material1Transition back to the ground state S by radiation0According to the spin statistics, the ratio of singlet excitons to triplet excitons in excitons is 1:3, so that the maximum internal quantum yield of the fluorescent material does not exceed 25%. According to the lambertian light emitting mode, the light extraction efficiency is about 20%, so the EQE of the OLED device based on the fluorescent material is not more than 5%.
Triplet excited state T of phosphorescent material1Attenuation of direct radiation to the ground state S0Due to the heavy atom effect, the internal intersystem crossing of the molecule can be enhanced through the spin coupling effect, 75 percent of triplet excitons can be directly utilized, and the S-type quantum well quantum1And T1The maximum theoretical internal quantum yield can reach 100 percent by jointly participating in emission. However, the phosphorescent material is basically a heavy metal complex such as Ir, Pt, Os, Re, Ru and the like, and the production cost is high, so that the large-scale production is not facilitated. Under high current density, the phosphorescent material has serious efficiency roll-off phenomenon, and the stability of the phosphorescent device is not good.
Two triplet excitons of TTA material interact to generate a singlet exciton, and the singlet exciton jumps back to the ground state S through radiation0The theoretical maximum internal quantum yield can only reach 62.5%. In order to prevent the generation of the large efficiency roll-off phenomenon, the concentration of triplet excitons needs to be regulated during this process.
TADF Material when S1State and T1Small energy gap value between states and T1Long service life of the state exciton, T under a certain temperature condition1The exciton can realize T by reverse intersystem crossing (RISC)1→S1By the process of S1Attenuation of state radiation to the ground state S0The difference between the singlet excited state and the triplet excited state is small, reverse intersystem crossing occurs in the molecule, and T1Thermal up-conversion of state excitons to S by absorption of ambient heat1State of being able toBy using 75% of triplet excitons and 25% of singlet excitons at the same time, the theoretical maximum internal quantum yield can reach 100%. Mainly organic compounds, does not need rare metal elements and has low production cost. Chemical modification can be performed by a variety of methods.
With the rapid development of OLED devices, the performance of most of the existing TADF materials cannot meet the requirements of the existing devices, and the properties of the TADF materials cause more difficulties in the process of device preparation, such as poor material solubility, which causes inconvenience to the evaporation process and the shutter cleaning process.
Therefore, there is a need in the art to develop more varieties of TADF materials with higher performance, and to facilitate the device fabrication process as much as possible.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a compound. The compound is a novel dual-core luminous electroluminescent compound connected by a flexible alkyl chain. The compound has a high triplet state energy level, and can improve the luminous efficiency of a device and reduce the driving voltage when being applied to an organic photoelectric device.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I or a formula II;
Figure BDA0002279719240000021
in the formulas I and II, X is C1-C5 (such as C2, C3, C4 and the like) alkylene or C1-C5 (such as C2, C3, C4 and the like) alkylene substituted by fluorine atoms;
in the formulae I and II, L1、L2、L3And L4Each independently selected from a single bond, a substituted or unsubstituted C6-C40 (e.g., C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) aryl group, a substituted or unsubstituted C3-C40 (e.g., C6, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroaryl group;
in the formulae I and II, D1、D2、D3、D4、D5And D6Each independently selected from any one of substituted or unsubstituted C6-C40 (e.g. C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) aryl, substituted or unsubstituted C4-C40 (e.g. C6, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroaryl, substituted or unsubstituted C12-C40 (e.g. C14, C16, C18, C20, C26, C28, C30, etc.) arylamine group, and D387321、D2、D3、D4、D5And D6Are all electron donating groups;
in the formula I and the formula II, A is1、A2、A3、A4、A5And A6Each independently selected from any one of aryl containing an electron-withdrawing group;
the electron-withdrawing group comprises any one or at least two of carbonyl, sulfuryl, boron atom, phosphorus oxygen group, amide group, nitrogen-containing heteroaryl and cyano;
in formula I and formula II, n1, n2, n3 and n4 are each independently 0 or 1, n1 and n2 are not 0 at the same time, and n3 and n4 are not 0 at the same time;
when the group includes a substituent as described above, the substituent includes at least one of a halogen group, a cyano group, a phenoxy group, an alkyl group of C1 to C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C15, C18, etc.), an alkoxy group of C1 to C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C15, C18, etc.), an aryl group of C6 to C40 (e.g., C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.), an aryl group of C4 to C40 (e.g., C6, etc.), or a combination of at least two kinds of arylamine.g, C6.
The invention provides a novel electroluminescent compound, wherein a flexible carbon chain X is introduced into the structure, so that the solubility of the compound can be increased, great convenience is provided for the synthesis, purification, evaporation and cleaning of a baffle of molecules, the sublimation temperature of the molecules is favorably reduced, and the novel electroluminescent compound is also very favorable for a device preparation process; also, since the conjugated structure is interrupted from the middle, the triplet level of such compounds can be increased.
In addition, both ends of the flexible carbon chain X contain an electron-donating unit and an electron-withdrawing unit (D-A unit), so that dual-core emission can be realized, and the luminous efficiency of luminous molecules is improved. Furthermore, each light emitting core of the structure is provided with the D-A connection element, and the push-pull electronic structure increases the carrier transmission rate, so that the driving voltage of the device during operation is reduced.
Another object of the present invention is to provide an organic photoelectric device including an anode, a cathode, and at least one organic thin film between the anode and the cathode, wherein the organic thin film includes a light-emitting layer containing the compound according to one of the objects.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a novel electroluminescent compound, wherein a flexible carbon chain X is introduced into the structure, so that the solubility of the compound can be increased, great convenience is provided for the synthesis, purification, evaporation and cleaning of a baffle of molecules, the sublimation temperature of the molecules is favorably reduced, and the novel electroluminescent compound is also very favorable for a device preparation process; also, since the conjugated structure is interrupted from the middle, the triplet level of such compounds can be increased.
In addition, both ends of the flexible carbon chain X contain an electron-donating unit and an electron-withdrawing unit (D-A unit), so that dual-core emission can be realized, and the luminous efficiency of luminous molecules is improved. Furthermore, each light emitting core of the structure is provided with the D-A connection element, and the push-pull electronic structure increases the carrier transmission rate, so that the driving voltage of the device during operation is reduced.
Drawings
FIG. 1 is a schematic illustration of an organic optoelectronic device provided in an embodiment of the present invention;
wherein: 1-a substrate; 2-ITO anode; 3-a hole injection layer; 4-a hole transport layer; 5-a light-emitting layer; 6-electron transport layer; 7-electron injection layer; 8-a cathode; 9-capping layer.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
One of the objects of the present invention is a compound having a structure represented by formula I or formula II;
Figure BDA0002279719240000031
in the formulas I and II, X is C1-C5 (such as C2, C3, C4 and the like) alkylene or C1-C5 (such as C2, C3, C4 and the like) alkylene substituted by fluorine atoms;
in the formulae I and II, L1、L2、L3And L4Each independently selected from a single bond, a substituted or unsubstituted C6-C40 (e.g., C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) aryl group, a substituted or unsubstituted C3-C40 (e.g., C6, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroaryl group;
in the formulae I and II, D1、D2、D3、D4、D5And D6Each independently selected from any one of substituted or unsubstituted C6-C40 (e.g. C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) aryl, substituted or unsubstituted C4-C40 (e.g. C6, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroaryl, substituted or unsubstituted C12-C40 (e.g. C14, C16, C18, C20, C26, C28, C30, etc.) arylamine group, and D387321、D2、D3、D4、D5And D6Are all electron donating groups;
in the formula I and the formula II, A is1、A2、A3、A4、A5And A6Each independently selected from any one of aryl containing an electron-withdrawing group;
the electron-withdrawing group comprises any one or at least two of carbonyl, sulfuryl, boron atom, phosphorus oxygen group, amide group, nitrogen-containing heteroaryl and cyano;
in formula I and formula II, n1, n2, n3 and n4 are each independently 0 or 1, n1 and n2 are not 0 at the same time, and n3 and n4 are not 0 at the same time;
when the group includes a substituent as described above, the substituent includes at least one of a halogen group, a cyano group, a phenoxy group, an alkyl group of C1 to C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C15, C18, etc.), an alkoxy group of C1 to C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C15, C18, etc.), an aryl group of C6 to C40 (e.g., C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.), an aryl group of C4 to C40 (e.g., C6, etc.), or a combination of at least two kinds of arylamine.g, C6.
The invention provides a novel electroluminescent compound, wherein a flexible carbon chain X is introduced into the structure, so that the solubility of the compound can be increased, great convenience is provided for the synthesis, purification, evaporation and cleaning of a baffle of molecules, the sublimation temperature of the molecules is favorably reduced, and the novel electroluminescent compound is also very favorable for a device preparation process; also, since the conjugated structure is interrupted from the middle, the triplet level of such compounds can be increased.
In addition, both ends of the flexible carbon chain X contain an electron-donating unit and an electron-withdrawing unit (D-A unit), so that dual-core emission can be realized, and the luminous efficiency of luminous molecules is improved. Furthermore, each light emitting core of the structure is provided with the D-A connection element, and the push-pull electronic structure increases the carrier transmission rate, so that the driving voltage of the device during operation is reduced.
In one embodiment, in formula I and formula II, one of n1 and n2 is 0.
In one embodiment, in formula I and formula II, one of n3 and n4 is 0.
According to the invention, one end of the flexible carbon chain X preferably only contains one D-A unit, and one D-A unit contributes to the effective separation of HOMO orbital and LUMO orbital, so that the formation of smaller singlet state and triplet state is facilitatedDifference of state energy level Δ ESTAnd the reverse system crossover (RISC) is further promoted to form the TADF effect, and the structure is more favorable for improving the luminous efficiency of the device. When both ends of the flexible carbon chain X only contain one D-A luminous unit, the effect is optimal.
In one embodiment, in formula I and formula II, the A is1、A2、A3And A4Selected from the same group.
In one embodiment, in formula I and formula II, the D is1And D2Selected from the same group.
In one embodiment, in formula I and formula II, the D is3、D4、D5And D6Selected from the same group.
In one embodiment, in formula I and formula II, the A is5And A6Selected from the same group.
The invention prefers to select the same group in the same molecular structure, so that the compound has the advantages of easily obtained raw materials, simpler synthesis, reduced organic synthesis steps, improved organic reaction yield and reduced process cost.
In one embodiment, in formula I and formula II, the D is1、D2、D3、D4、D5And D6Each independently selected from any one of substituted or unsubstituted C12-C40 (such as C14, C16, C18, C20, C26, C28, C30 and the like) arylamine groups, substituted or unsubstituted C10-C40 carbazole groups, substituted or unsubstituted C12-C40 (such as C14, C16, C18, C20, C26, C28, C30 and the like) acridine groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted diphenyl ether groups and substituted or unsubstituted diindolopentadiene groups;
when the group contains a substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine.
Further preferred according to the invention D1、D2、D3、D4、D5And D6The electron donating groups are selected from the specific electron donating groups, have better electron donating capability, can be modified by groups to adjust the electron donating capability, and have better thermal stability and redox stability, so that the service life of the device is prolonged.
In the present invention, D3、D4、D5And D6Only contains one connecting position, and D has different values according to n1, n2, n3 and n41And D2May contain 2 or 3 linking positions, illustratively, D when only one of n1 and n2 takes 11With two attachment positions, but with both n1 and n2 taking 1, D1There are three attachment locations; a. the1、A2、A3、A4、A5And A6In the same way, A1、A2、A3And A4Containing only one connecting position, A5And A6May contain 2 or 3 attachment positions;
therefore, D is defined hereinafter1、D2、D3、D4、D5、D6、A1、A2、A3、A4、A5And A6The specific structure of (3) may be such that the number of the connecting sites is different.
In one embodiment, the substituted or unsubstituted C10-C40 carbazole group specifically includes the following substituted or unsubstituted groups:
Figure BDA0002279719240000051
y is selected from any one of carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms and silicon atoms;
a is an integer of 0-2;
the R is1Selected from hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstitutedAny one of C3-C30 heteroaryl;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
The series of carbazole groups with specific structures are further preferred, carbazole is diphenylamine molecules with an isoelectronic structure, particularly the groups with the structures have strong electron-donating capacity and good hole transmission capacity, active sites on the groups are more, various functional groups are easily introduced to functionalize the groups, and when the carbazole groups are applied to the compound, high-efficiency luminescent groups are easily introduced through modification of the molecular structures, so that the luminescent material with excellent performance is obtained.
In one embodiment, the substituted or unsubstituted C12-C40 acridine group specifically comprises the following substituted or unsubstituted groups:
Figure BDA0002279719240000061
y and Z are independently selected from any one of carbon atom, nitrogen atom, oxygen atom, sulfur atom and silicon atom;
a and b are each independently selected from integers of 0-2;
the R is1And R2Each independently selected from any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
Further preferred are a series of acridine groups having a specific structure, which have a macrocyclic conjugated system having a rigid planar structure, are excellent in fluorescence properties, and have a large pi-conjugated system structure. The material taking the group as the electron-donating group has high luminous efficiency, reasonable energy level structure and good host-guest energy transfer characteristics, and a device taking the material as the luminous layer has good luminous performance.
In one embodiment, the substituted or unsubstituted C12-C40 arylamine group specifically includes the following substituted or unsubstituted groups:
Figure BDA0002279719240000071
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
The arylamine groups with the specific structures are further preferably selected, the groups have good electron-giving capacity, good thermal stability and oxidation-reduction stability, and the molecular configuration has good non-planarity, so that intermolecular accumulation can be inhibited, and the luminous efficiency of the device is further improved.
In one embodiment, said D1、D2Each independently selected from any one of the following substituted or unsubstituted groups:
Figure BDA0002279719240000081
said D3、D4、D5And D6Each independently selected from any one of the following substituted or unsubstituted groups:
Figure BDA0002279719240000082
y is selected from any one of carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms and silicon atoms;
a is an integer of 0-2;
the R is1Any one selected from a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
Furthermore, it is preferable that the electron-donating group has the above-mentioned specific structure, and these groups have good electron-donating ability, and the electron-donating ability can be adjusted by modifying the groups, and in addition, these groups have good thermal stability and redox stability, thereby improving the lifetime of the device.
In one embodiment, said a1、A2、A3、A4Each independently selected from any one of the following substituted or unsubstituted groups:
Figure BDA0002279719240000091
Figure BDA0002279719240000101
Figure BDA0002279719240000111
a is described5And A6Each independently selected from any one of the following substituted or unsubstituted groups:
Figure BDA0002279719240000121
Figure BDA0002279719240000131
Figure BDA0002279719240000141
r is selected from any one of C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl and C4-C40 heteroaryl;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
Further, it is preferable that the electron-withdrawing group has the above-mentioned specific structure, and such a structure has a good electron-donating ability, and the electron-donating ability thereof can be easily adjusted by group modification. In addition, the structures have good thermal stability and oxidation-reduction stability, and the service life of the device can be prolonged.
In one embodiment, said L is1、L2、L3And L4Each independently selected from any one of single bond, phenylene, thienylene, naphthylene, anthrylene, phenanthrylene or pyrenylene.
In the present invention, it is preferable that the connection unit between the electron donating group and the electron withdrawing group is a single bond or the above group, so that it is possible to prevent the HOMO orbital and the LUMO orbital from being excessively separated, even if the HOMO orbital and the LUMO orbital of the molecule overlap to some extent, thereby improving the photoluminescence quantum yield (PLQY) of the molecule and improving the light emitting efficiency of the molecule.
In one embodiment, the compound has any one of the following structures represented by P1 to P63:
Figure BDA0002279719240000151
Figure BDA0002279719240000171
Figure BDA0002279719240000191
Figure BDA0002279719240000201
Figure BDA0002279719240000211
another object of the present invention is to provide an organic photoelectric device including an anode, a cathode, and at least one organic thin film between the anode and the cathode, wherein the organic thin film includes a light-emitting layer containing the compound according to one of the objects.
In one embodiment, the compound according to one of the objects serves as a host material, a dopant material, or a co-dopant material of the light-emitting layer.
In one embodiment, the organic thin layer further includes any one or at least two combinations of a hole transport layer, a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
In the organic photoelectric device, the anode material may be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof. The anode material may also be selected from metal oxides such as indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; the anode material may also be selected from conductive polymers such as polyaniline, polypyrrole, poly (3-methylthiophene), and the like. In addition, the anode material may also be selected from materials that facilitate hole injection in addition to the anode materials listed above, and combinations thereof, including known materials suitable for use as anodes.
In the organic photoelectric device, the cathode material may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof. The cathode material may also be selected from multi-layered metallic materials such as LiF/Al, LiO2/Al、BaF2Al, etc. In addition to the cathode materials listed above, the cathode materials can also be materials that facilitate electron injection and combinations thereof, including materials known to be suitable as cathodes.
In the embodiment of the present invention, the manufacturing process of the organic photoelectric device is as follows: an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer. The organic thin layer can be formed by a known film formation method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like. Finally, an organic optical cover layer CPL (cap layer) is prepared on the cathode. CPL can be prepared by evaporation or solution processing. Solution processing methods include ink jet printing, spin coating, doctor blade coating, screen printing, roll-to-roll printing, and the like.
The synthesis method of the compound with the structure of the chemical formula I provided by the invention comprises the following steps:
the donor moiety is attached to both ends of the alkyl chain by a suitable method (for example, by removing active hydrogen or bromine from the donor group using butyl lithium, and then reacting with an alkyl chain having bromine at both ends), and then the acceptor moiety is attached to the donor moiety by chemical coupling or the like.
The synthesis method of the compound with the structure of the chemical formula II provided by the invention comprises the following steps:
the acceptor moiety is attached to both ends of the alkyl chain by a suitable method (for example, removing active hydrogen or bromine from the acceptor group by using butyl lithium, and then reacting with the alkyl chain having bromine at both ends), and then the donor moiety is attached to the acceptor moiety by chemical coupling or the like.
The compounds of formula I and formula II of the present invention can be synthesized by the above-mentioned methods, but are not limited thereto.
The present invention provides several exemplary methods for the preparation of the compounds. In the subsequent preparation examples, the synthesis of compounds P1, P2, P3, P4, P55, P63 is exemplarily described.
Preparation example 1 Synthesis of Compound P1
Figure BDA0002279719240000221
S2(2mmol) is dissolved in Tetrahydrofuran (THF) under the protection of nitrogen at-78 ℃, BuLi (2mmol) is added dropwise, after half an hour of reaction, S1(1mmol) is diluted in a small amount of THF solution and added dropwise into a reaction bottle, after half an hour of reaction at-78 ℃, the reaction is carried out at normal temperature overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: chloroform (5:1) as eluent, and finally purified to obtain S3(0.86mmol, 86%) as a solid. TMS represents trimethyl.
MALDI-TOF MS：C43H42N2Si2Calculated m/z: 642.98, mol.wt.: 642.98; measurement values: 642.29.
s3(1mmol) and N-bromosuccinimide (NBS, 3mmol) were dissolved in Chloroform (CF) under nitrogen and stirred at room temperature overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: a mixed solvent of chloroform (5:1) was used as an eluent, and finally purified to obtain S4(0.92mmol, 92%) as a solid.
MALDI-TOF MS：C37H24Br2N2Calculated m/z: m656.41, ol.wt.: 656.41; measurement values: 656.03.
Figure BDA0002279719240000223
weighing the compounds S4(1mmol), S5(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal for 15 min), then 5mL of 1M (mol/L) K was added dropwise2CO3Aqueous solution (Advance N)215min deoxygenation), stirring overnight at 120 ℃. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give P1 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: C67H44N8: 961.12; test values are: 960.37. theoretical value of elemental analysis: c, 83.73; h, 4.61; n, 11.66; actual value C, 83.72; h, 4.62; n, 11.66.
Preparation example 2 Synthesis of Compound P2
Figure BDA0002279719240000231
S2(2mmol) was dissolved in THF at-78 deg.C under nitrogen protection, BuLi (2mmol) was added dropwise, after half an hour of reaction, S6(1mmol) was diluted in a small amount of THF solution, dropwise added to the reaction flask, after half an hour of reaction at-78 deg.C, and then, at room temperature overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography using a mixed solvent of n-hexane and chloroform (5:1) as an eluent to finally purify S7(0.86mmol, 86%) as a solid.
MALDI-TOF MS：C44H44N2Si2Calculated m/z: 657.00, mol.wt.: 657.00; measurement values: 656.30.
Figure BDA0002279719240000232
s7(1mmol) and NBS (3mmol) were dissolved in chloroform under nitrogen and stirred overnight at room temperature. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: a mixed solvent of chloroform (5:1) was used as an eluent, and finally purified to obtain S8(0.92mmol, 92%) as a solid.
MALDI-TOF MS：C38H26Br2N2Calculated m/z: 670.43, mol.wt.: 670.43; measurement values: 670.04.
Figure BDA0002279719240000233
weighing the compounds S8(1mmol), S5(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal for 15 min), then 5mL of 1M K were added dropwise2CO3Aqueous solution (Advance N)215min deoxygenation), stirring overnight at 120 ℃. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give P2 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c68H46N8975.15; test values are: 974.38.
theoretical value of elemental analysis: c, 83.75; h, 4.75; n, 11.49; actual value C, 83.74; h, 4.74; n, 11.52.
Preparation example 3 Synthesis of Compound P3
Figure BDA0002279719240000241
S2(2mmol) was dissolved in THF at-78 deg.C under nitrogen protection, BuLi (2mmol) was added dropwise, after half an hour of reaction, S9(1mmol) was diluted in a small amount of THF solution, dropwise added to the reaction flask, after half an hour of reaction at-78 deg.C, and then, at room temperature overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: chloroform (5:1) as eluent, and finally purified to obtain S10(0.86mmol, 86%) as a solid.
MALDI-TOF MS：C45H46N2Si2Calculated m/z: 671.03, mol.wt.: 671.03; measurement values: 670.32.
Figure BDA0002279719240000242
s10(1mmol) and NBS (3mmol) were dissolved in chloroform under nitrogen and stirred overnight at room temperature. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: a mixed solvent of chloroform (5:1) was used as an eluent, and finally purified to obtain S11(0.92mmol, 92%) as a solid.
MALDI-TOF MS：C39H28Br2N2Calculated m/z: 684.46, mol.wt.: 684.46; measurement values: 684.06.
Figure BDA0002279719240000243
weighing the compounds S11(1mmol), S5(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal for 15 min), then 5mL of 1M K were added dropwise2CO3Aqueous solution (Advance N)215min deoxygenation), stirring overnight at 120 ℃. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give P3 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c69H48N8989.17; test values are: 988.40. theoretical value of elemental analysis: c, 83.78; h, 4.89; n, 11.33; actual value C, 83.75; h, 4.90; n, 11.35.
Preparation example 4 Synthesis of Compound P4
Figure BDA0002279719240000244
S1(2mmol) was dissolved in THF at-78 deg.C under nitrogen protection, BuLi (2mmol) was added dropwise, after half an hour of reaction, S11(1mmol) was diluted in a small amount of THF solution, dropwise added to the reaction flask, after half an hour of reaction at-78 deg.C, and then, at room temperature overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: chloroform (5:1) as eluent, and finally purified to obtain S12(0.86mmol, 86%) as a solid.
MALDI-TOF MS：C46H48N2Si2Calculated m/z: 685.06, mol.wt.: 685.06; measurement values: 684.34.
Figure BDA0002279719240000251
s12(1mmol) and NBS (3mmol) were dissolved in chloroform under nitrogen and stirred overnight at room temperature. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: a mixed solvent of chloroform (5:1) was used as an eluent, and finally purified to obtain S13(0.92mmol, 92%) as a solid.
MALDI-TOF MS：C40H30Br2N2Calculated m/z: 698.49, mol.wt.: 698.49; measurement values: 698.08.
weighing the compounds S13(1mmol), S5(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal for 15 min), then 5mL of 1M K were added dropwise2CO3Aqueous solution (Advance N)215min deoxygenation), stirring overnight at 120 ℃. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give P4 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c70H50N81003.20; test values are: 1002.42.
theoretical value of elemental analysis: c, 83.81; h, 5.02; n, 11.17; actual value C, 83.82; h, 5.02; n, 11.16.
Preparation example 5 Synthesis of Compound P55
Figure BDA0002279719240000253
S14(2mmol) was dissolved in THF at-78 deg.C under nitrogen protection, BuLi (2mmol) was added dropwise, after half an hour of reaction, S9(1mmol) was diluted in a small amount of THF solution, dropwise added to the reaction flask, after half an hour of reaction at-78 deg.C, and then, at room temperature overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and all the solvent was removed by distillation under the reduced pressure to collect a crude product. The crude product was purified by silica gel chromatography column, eluting with n-hexane: chloroform (5:1) as eluent, and finally purified to obtain S15(0.86mmol, 86%) as a solid.
MALDI-TOF MS：C15H14Br2Calculated m/z: 354.08, mol.wt.: 354.08; measurement values: 353.94.
Figure BDA0002279719240000254
weighing the compounds S15(1mmol), S16(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal for 15 min), then 5mL of 1M K were added dropwise2CO3Aqueous solution (Advance N)215min deoxygenation), stirring overnight at 120 ℃. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give P55 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c69H52N8993.20; test values are: 992.43.
theoretical value of elemental analysis: c, 83.44; h, 5.28; n, 11.28; actual value C, 83.45; h, 5.26; n, 11.29.
Preparation example 6 Synthesis of Compound P63
Figure BDA0002279719240000261
Weighing the compounds S15(1mmol), S16(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen is removed in 15 min), and the mixture is heated under reflux for 12 h. After the reaction was completed, 15mL of deionized water was added, extraction was performed with methylene chloride, and the organic phase was collected and extracted with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give S17 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c39H30N2526.67; test values are: 526.24.
Figure BDA0002279719240000262
weighing the compounds S17(1mmol), S18(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol), sodium ethoxide (NaOEt, 0.5mmol) was added to a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal is carried out for 15 min), and heating reflux is carried out for 12 h. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give P63 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c123H82N141756.06; test values are: 1755.69.
theoretical value of elemental analysis: c, 84.13; h, 4.71; n, 11.17; actual value C, 84.11; h, 4.71; n, 11.18.
Comparative preparation example 1 Synthesis of Compound C1
Figure BDA0002279719240000271
Weighing the compounds S19(1mmol), S18(2mmol) and Pd (PPh) under the protection of nitrogen3)4(0.10mmol), NaOEt (0.5mmol) was charged into a 250mL two-necked flask. 60mL of toluene (N was introduced into the flask in advance)2Oxygen removal is carried out for 15 min), and heating reflux is carried out for 12 h. After the reaction was complete, 15mL of deionized water was added and a few drops of 2M HCl were added dropwise. Extracting with dichloromethane, collecting organic phase, and extracting with anhydrous Na2SO4And (5) drying. The dried solution was filtered and the solvent was removed using a rotary evaporator to give the crude product. The crude product was purified by silica gel chromatography to give C1 as a solid (0.72mmol, 72%).
MALDI-TOF MS: m/z, calculated value: c66H42N8947.09; test values are: 946.35.
theoretical value of elemental analysis: c, 83.70; h, 4.47; n, 11.83; actual value C, 83.71; h, 4.45; n, 11.84.
Performance test compound simulation calculations
The distribution of the molecular front orbitals is optimized and calculated by applying the Density Functional Theory (DFT) to the compounds of the invention used in the examples and the comparative examples under the calculation level of B3LYP/6-31G (d) by utilizing the Gaussian 09 program package; meanwhile, based on the time-density functional theory (TD-DFT), the singlet state energy level S of the molecule is calculated in a simulation mode1And triplet state energy level T1The results are shown in Table 1, wherein △ EST＝S1-T1，Eg＝HOMO-LUMO，EgThe absolute value of (a) is taken.
TABLE 1
Compound (I) HOMO(eV) LUMO(eV) S1(eV) T1(eV) △EST(eV) Eg(eV)
P1 -5.205 -1.943 3.035 2.803 0.23 3.26
P2 -5.208 -1.952 3.01 2.790 0.22 3.26
P3 -5.206 -1.961 3.0112 2.791 0.22 3.25
P4 -5.231 -1.951 3.027 2.792 0.23 3.28
P55 -5.340 -1.967 3.116 2.826 0.29 3.37
P63 -5.621 -1.776 3.532 2.741 0.79 3.84
C1 -5.000 -1.963 2.875 2.431 0.44 3.04
As can be seen from table 1, the dual-core luminescent material designed in this case has deeper singlet and triplet energy levels, and simultaneously has a HOMO energy level and a LUMO energy level in an appropriate range, and can be well matched with a general electron transport layer material or a hole transport layer material, and is suitable for a host material in a blue luminescent layer.
As shown in fig. 1, another aspect of the present invention provides an organic photoelectric device including: the structure of the thin film transistor comprises a substrate 1, an ITO anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8 (a magnesium silver electrode, the mass ratio of magnesium to silver is 9:1) and a cap layer (CPL)9, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the hole injection layer 3 is 10nm, the thickness of the hole transport layer 4 is 110nm, the thickness of the light emitting layer 5 is 30nm, the thickness of the electron transport layer 6 is 30nm, the thickness of the electron injection layer 7 is 5nm, the thickness of the cathode 8 is 15nm and the thickness of the cap layer 9 is 100 nm. The arrows in fig. 1 represent the light extraction direction of the organic electroluminescent device.
Example 1
In this embodiment, the compound of the present invention is used as a blue light host material to prepare an organic photoelectric device, and the preparation steps are as follows:
1) the glass substrate was cut into a size of 50mm × 50mm × 0.7mm, sonicated in isopropanol and deionized water, respectively, for 30 minutes, and then exposed to ozone for about 10 minutes to clean. Mounting the resulting glass substrate with Indium Tin Oxide (ITO) anode on a vacuum deposition apparatus;
2) evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
3) vacuum evaporating a hole transport layer material TAPC on the hole injection layer 3, wherein the thickness of the hole transport layer material TAPC is 110nm and is used as a hole transport layer 4;
4) a luminescent layer 5 is vacuum-evaporated on the hole transport layer 4, wherein the compound P1 is used as a host material, BCzVBi is used as a fluorescent doping material, the doping proportion is 3% (mass ratio), and the thickness is 30 nm;
5) vacuum evaporating an electron transport layer material TPBI on the light-emitting layer 5, wherein the thickness of the electron transport layer material TPBI is 30nm, and the electron transport layer material TPBI is used as an electron transport layer 6;
6) vacuum evaporation of electron injection layer material Alq on the electron transport layer 635nm thick as an electron injection layer 7;
7) a magnesium silver electrode is evaporated on the electron injection layer 7 in vacuum, wherein the ratio of Mg to Ag is 9:1, the thickness is 15nm, and the magnesium silver electrode is used as a cathode 8;
8) HT was vacuum-deposited on the cathode 8 to a thickness of 100nm, and used as a cap layer 9.
Figure BDA0002279719240000281
Examples 2 to 6 and comparative example 1 differ from example 1 only in the replacement of the host material of the light-emitting layer, as detailed in table 2.
Performance evaluation of Performance test organic optoelectronic devices
The current at different voltages of the organic photoelectric devices manufactured according to the examples and comparative examples was measured using a Keithley 2365A digital nano-voltmeter, and then the current was divided by the light emitting area to obtain the current densities at different voltages of the organic photoelectric devices. Organic optoelectronic devices fabricated according to the examples and comparative examples were tested on various devices using a Konicaminolta CS-2000 spectroradiometerBrightness at voltage and radiant fluence. According to the current density and the brightness of the organic photoelectric device under different voltages, the current density (10 mA/cm) under the same current density is obtained2) Current efficiency (CE, cd A)-1) (ii) a Corresponding to 10mA/cm in the above-measured current-voltage-luminance curve2The lower voltage is the driving voltage V of the deviceon；
The test results are shown in table 2.
TABLE 2
Figure BDA0002279719240000282
Figure BDA0002279719240000291
As is apparent from Table 2, V of the organic light emitting device using P1, P2, P53, P4, P55, P63 as host materials was compared with comparative device example 1 using Compound C1 in the comparative example as blue fluorescent host materialonAre all significantly lower than the comparative devices and the current efficiencies are all significantly higher than the comparative devices. The appropriate energy level positions and singlet state energy levels of P1, P2, P53, P4, P55 and P63 dual-core emission host materials and excellent hole and electron transport efficiency are mainly benefited, so that the driving voltage of the device is reduced, and the efficiency of the device is improved.
The applicant states that the present invention is illustrated by the above examples to show the detailed process equipment and process flow of the present invention, but the present invention is not limited to the above detailed process equipment and process flow, i.e. it does not mean that the present invention must rely on the above detailed process equipment and process flow to be implemented. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (18)

1. A compound having a structure according to formula I or formula II;
Figure FDA0002279719230000011
in the formula I and the formula II, X is C1-C5 alkylidene or C1-C5 alkylidene substituted by fluorine atoms;
in the formulae I and II, L1、L2、L3And L4Each independently selected from any one of single bond, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C3-C40 heteroaryl;
in the formulae I and II, D1、D2、D3、D4、D5And D6Each independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl and substituted or unsubstituted C12-C40 arylamine groups, and D1、D2、D3、D4、D5And D6Are all electron donating groups;
in the formula I and the formula II, A is1、A2、A3、A4、A5And A6Each independently selected from any one of aryl containing an electron-withdrawing group;
the electron-withdrawing group comprises any one or at least two of carbonyl, sulfuryl, boron atom, phosphorus oxygen group, amide group, nitrogen-containing heteroaryl and cyano;
in formula I and formula II, n1, n2, n3 and n4 are each independently 0 or 1, n1 and n2 are not 0 at the same time, and n3 and n4 are not 0 at the same time;
when the group contains a substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine.
2. The compound of claim 1, wherein one of n1 and n2 is 0 in formula I and formula II.
3. The compound of claim 1, wherein one of n3 and n4 is 0 in formula I and formula II.
4. The compound of claim 1, wherein in formula I and formula II, a is1、A2、A3And A4Selected from the same group.
5. The compound of claim 1, wherein D is as defined in formula I and formula II1And D2Selected from the same group.
6. The compound of claim 1, wherein D is as defined in formula I and formula II3、D4、D5And D6Selected from the same group.
7. The compound of claim 1, wherein in formula I and formula II, a is5And A6Selected from the same group.
8. The compound of claim 1, wherein D is as defined in formula I and formula II1、D2、D3、D4、D5And D6Each independently selected from any one of substituted or unsubstituted C12-C40 arylamine groups, substituted or unsubstituted C10-C40 carbazole groups, substituted or unsubstituted C12-C40 acridine groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted diphenyl ether groups and substituted or unsubstituted diindolopentadiene groups;
when the group contains a substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine.
9. The compound of claim 8, wherein the substituted or unsubstituted C10-C40 carbazole group specifically includes the following substituted or unsubstituted groups:
y is selected from any one of carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms and silicon atoms;
a is an integer of 0-2;
the R is1Any one selected from a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
10. The compound according to claim 8, wherein said substituted or unsubstituted C12-C40 acridine group specifically comprises the following substituted or unsubstituted groups:
Figure FDA0002279719230000041
Figure FDA0002279719230000051
y and Z are independently selected from any one of carbon atom, nitrogen atom, oxygen atom, sulfur atom and silicon atom;
a and b are each independently selected from integers of 0-2;
the R is1And R2Each independently selected from the group consisting of hydrogen atoms, and hydrogen atomsAny one of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
11. The compound of claim 8, wherein the substituted or unsubstituted C12-C40 aromatic amine groups specifically include the following substituted or unsubstituted groups:
Figure FDA0002279719230000061
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
12. The compound of claim 1, wherein D is1、D2Each independently selected from any one of the following substituted or unsubstituted groups:
Figure FDA0002279719230000062
Figure FDA0002279719230000071
said D3、D4、D5And D6Each independently selected from the group consisting of substituted and unsubstitutedAny one of the groups:
y is selected from any one of carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms and silicon atoms;
a is an integer of 0-2;
the R is1Any one selected from a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
13. The compound of claim 1, wherein a is1、A2、A3、A4Each independently selected from any one of the following substituted or unsubstituted groups:
Figure FDA0002279719230000081
Figure FDA0002279719230000101
a is described5And A6Each independently selected from any one of the following substituted or unsubstituted groups:
Figure FDA0002279719230000111
Figure FDA0002279719230000131
r is selected from any one of C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl and C4-C40 heteroaryl;
when the groups contain the substituent, the substituent comprises any one or at least two of halogen, cyano, phenoxy, C1-C20 alkyl, C1-C20 alkoxy, C6-C40 aryl, C4-C40 heteroaryl and C6-C40 arylamine;
wherein, # denotes the attachment position of the group.
14. The compound of claim 1, wherein L is1、L2、L3And L4Each independently selected from any one of single bond, phenylene, thienylene, naphthylene, anthrylene, phenanthrylene or pyrenylene.
15. The compound of claim 1, wherein the compound has any one of the following structures P1-P63:
Figure FDA0002279719230000151
Figure FDA0002279719230000161
Figure FDA0002279719230000171
Figure FDA0002279719230000191
Figure FDA0002279719230000201
16. an organic photoelectric device comprising an anode, a cathode, and at least one organic thin film between the anode and the cathode, wherein the organic thin film comprises a light-emitting layer containing the compound according to any one of claims 1 to 15.
17. The organic photoelectric device according to claim 16, wherein the compound according to any one of claims 1 to 16 is used as a host material, a dopant material, or a co-dopant material of a light-emitting layer.
18. The organic photoelectric device according to claim 16, wherein the organic thin layer further comprises any one or a combination of at least two of a hole transport layer, a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
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