CN112321630A - Electron donor compound, method for producing the same, light-emitting device, and display device - Google Patents

Electron donor compound, method for producing the same, light-emitting device, and display device Download PDF

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CN112321630A
CN112321630A CN201911376831.8A CN201911376831A CN112321630A CN 112321630 A CN112321630 A CN 112321630A CN 201911376831 A CN201911376831 A CN 201911376831A CN 112321630 A CN112321630 A CN 112321630A
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electron donor
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苏亮
周兴邦
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Guangdong Juhua Printing Display Technology Co Ltd
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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Abstract

The invention relates to an electron donor compound, a light-emitting device, a preparation method thereof and a display device. The electron donor compound has a group having a structure shown below:
Figure DDA0002341194080000011
each R is1Independently selected from hydrogen, trimethylsilyl, cyclohexyl, 3-pentyl, 4- (9,9' -spirobifluorene) yl, 2- (9, 9-diphenylfluorene) yl or tetraphenylvinyl; and each R1Not hydrogen at the same time. When the electron donor compound is used as an electron donor material and applied to an interface heterojunction exciplex system, the original electron donor and electronThe contact points of the sub-receptors are isolated by the non-hydrogen substituent, so that electrons and holes are separated in space, and the electrons of the electron receptor layer can be prevented or hindered from easily moving into the electron donor layer, so that the electrification problem of the quantum dots is avoided or relieved, and the efficiency and the service life of the light-emitting device are improved.

Description

Electron donor compound, method for producing the same, light-emitting device, and display device
Technical Field
The invention relates to the technical field of display, in particular to an electron donor compound, a light-emitting device, a preparation method of the light-emitting device and a display device.
Background
The Organic Light Emitting Diode (OLED) is well optimized after years of development, and the product is verified by the market. However, the luminous efficiency and the lifetime of the OLED have yet to be improved based on market demands.
Quantum dot electroluminescent diodes (QLEDs) have recently been receiving wide attention and research in the display field due to their unique optical properties, such as continuously adjustable emission wavelength with size and composition, narrow emission spectrum, high fluorescence efficiency, and good stability.
Through years of research, the development of QLEDs has formed two basic light emitting mechanisms: direct charge injection and energy transfer. In the direct charge injection mechanism, the introduction of a ZnO electron transport layer and the optimization of a quantum dot core-shell structure are benefited, so that the performance of the QLED is greatly improved, for example: the maximum external quantum efficiency of the red and green QLEDs is over 20 percent, and the maximum external quantum efficiency of the blue QLED is increasingly close to 20 percent. However, the QLED has the problems of excessive electrons, and the unfavorable results of quantum dot Auger recombination, hole transport layer degradation and the like caused by the problems, so that the stability and the service life of the QLED are seriously limited.
Therefore, the quantum dot obtained by utilizing the energy transfer principle is increasingly and widely concerned, and under the mode, the quantum dot is not charged, but only receives excitons transferred by the host material, so that the problem of excessive charge does not exist theoretically, and a new thought is provided for improving the stability and the service life of the QLED. Therefore, exciplex systems (consisting of electron donor molecules and electron acceptor molecules) are widely studied in the field of QLEDs. However, the inventors have studied and found that, in a conventional light emitting device in which a quantum dot is directly doped in an exciplex system, since the conduction band bottom level of the quantum dot is greater than the LUMO level of an electron acceptor in the exciplex system, an electron is very easily trapped by the quantum dot, a sufficient exciplex exciton cannot be efficiently formed, and a charging effect cannot be avoided by the quantum dot. Therefore, in the prior art, the efficiency of preparing the QLED based on the energy transfer mechanism is low by using the exciplex system as a host and the quantum dot as a guest.
Disclosure of Invention
In view of the above, it is necessary to provide an electron donor compound, a light emitting device, a method for producing the same, and a display device, in order to solve the problems that the efficiency and lifetime of the conventional light emitting device are to be improved.
An electron donor compound having a group of the structure shown below:
Figure BDA0002341194060000021
each R is1Independently selected from hydrogen, trimethylsilyl, cyclohexyl, 3-pentyl, 4- (9,9' -spirobifluorene) yl, 2- (9, 9-diphenylfluorene) yl or tetraphenylvinyl; and each R1Not hydrogen at the same time.
Based on the above, the substituent is introduced into the peripheral site of the electron donor compound to obtain a new electron donor compound, the substituent has steric hindrance effect and is shown as insulating property, when the new electron donor compound is used as an electron donor material in an interface heterojunction exciplex system, the contact point of the original electron donor and the electron acceptor is isolated by the non-hydrogen substituent, so that electrons and holes are separated in space, electrons in the electron acceptor layer can be prevented or hindered from easily moving into the electron donor layer, the charging problem of quantum dots is avoided or relieved, and the efficiency and the service life of a light-emitting device are improved.
In one embodiment, the electron donor compound has the general structural formula shown in formula (I):
Figure BDA0002341194060000031
wherein L is a single bond or
Figure BDA0002341194060000032
In one embodiment, the electron donor compound has the general formula shown in formula (Ia) or formula (Ib):
Figure BDA0002341194060000033
in one embodiment, the compound is selected from one of the following compounds M1-M12:
Figure BDA0002341194060000034
Figure BDA0002341194060000041
the invention provides a preparation method of an electron donor compound, which comprises the following steps:
a compound of formula (II) and a compound containing R1The compound of the group is prepared by coupling reaction; said compound containing R1The compound of the group is trimethyl chlorosilane, 1-cyclohexane borate, 3-pentane borate, 4-spirobifluorene borate, 2-9, 9-diphenylfluorene borate or 1- (4-phenyl borate) -1,2, 2-triphenylethylene;
the general formula of the compound shown in the formula (II) is as follows:
Figure BDA0002341194060000042
wherein L is a single bond or
Figure BDA0002341194060000051
Each R is2Independently selected from hydrogen or halogen groups.
The invention provides a composition comprising the electron donor compound or the electron donor compound prepared by the preparation method and at least one organic solvent.
The invention also provides the application of the electron donor compound, the electron donor compound prepared by the preparation method, or the composition in preparing a light-emitting device.
A light emitting device comprising an electron donor molecule having a structure comprising trimethylsilyl, cyclohexyl, 3-pentyl, 4- (9,9' -spirobifluorene) yl, 2- (9, 9-diphenylfluorene) yl, or tetraphenylvinyl.
In one embodiment, the electron donor molecule is any of the electron donor compounds described herein or an electron donor compound prepared by the preparation method described herein.
In one embodiment, the light emitting device further comprises an electron donor layer containing the electron donor molecules.
In one embodiment, the light emitting device further comprises an electron acceptor layer in direct contact with the electron donor layer, the electron donor layer and the electron acceptor layer being capable of forming an interfacial heterojunction exciplex therebetween.
In one embodiment, the electron donor layer further comprises a quantum dot material intermixed with the electron donor molecules.
In one embodiment, the material of the electron acceptor layer is selected from at least one of 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline and tris (2,4, 6-trimethyl-3- (pyridin-3-yl) phenyl) borane.
The invention provides a display device including the light-emitting device of any one of the above.
Drawings
Fig. 1 is a schematic structural view of a light-emitting device according to an embodiment of the present invention.
Detailed Description
The present invention will be described in detail with reference to the accompanying drawings, which illustrate embodiments of the present invention. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The invention provides an electron donor compound, and a preparation method thereof, wherein the electron donor compound has a group with a structure shown as the following formula:
Figure BDA0002341194060000061
each R is1Independently selected from hydrogen, trimethylsilyl, cyclohexyl, 3-pentyl, 4- (9,9' -spirobifluorene) yl, 2- (9, 9-diphenylfluorene) yl or tetraphenylvinyl; and each R1Not hydrogen at the same time.
The substituent group is introduced into the peripheral site of the electron donor compound to obtain a new electron donor compound, the substituent group has steric hindrance effect and is shown as insulating property, when the new electron donor compound is used as an electron donor material in an interface heterojunction exciplex system, the contact point of the original electron donor and the electron acceptor is isolated by the non-hydrogen substituent group, so that electrons and holes are separated in space, electrons in the electron acceptor layer can be prevented or hindered from easily moving into the electron donor layer, the charge problem of quantum dots is avoided or relieved, and the efficiency and the service life of a light-emitting device are improved.
In one embodiment, the electron donor compound has the general structural formula shown in formula (I):
Figure BDA0002341194060000071
wherein L is a single bond or
Figure BDA0002341194060000072
In one embodiment, the electron donor compound has the general formula shown in formula (Ia) or formula (Ib):
Figure BDA0002341194060000073
in one embodiment, the electron donor compound is selected from one of the following compounds represented by M1-M12:
Figure BDA0002341194060000081
further, the present invention also provides a method for preparing an electron donor compound, comprising the steps of:
a compound of formula (II) and a compound containing R1The compound of the group is prepared by coupling reaction; said compound containing R1The compound of the group is trimethyl chlorosilane, 1-cyclohexane borate, 3-pentane borate, 4-spirobifluorene borate, 2-9, 9-diphenylfluorene borate or 1- (4-phenyl borate) -1,2, 2-triphenylethylene;
the general formula of the compound shown in the formula (II) is as follows:
Figure BDA0002341194060000091
wherein L is a single bond or
Figure BDA0002341194060000092
Each R is2Independently selected from hydrogen or halogen groups.
Further, when R is2In the case of halogen radicals, R is present after completion of the reaction2By R1Preferably, the halogen group is bromo.
Further, the compound represented by formula (II) may be hexabromo-TCTA or 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl, and the structural formula is as follows:
Figure BDA0002341194060000093
in one embodiment, the coupling reaction of the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl with trimethylchlorosilane comprises the steps of: under the atmosphere of protective gas, a compound hexabromo-TCTA or a compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl is placed in a tetrahydrofuran solvent (THF), n-butyl lithium (n-BuLi) is dropwise added at the temperature of-80 ℃ and the temperature of 8-70 ℃, the reaction is carried out for 2H84H, and then trimethylchlorosilane ((CH)3)3SiCl) at-80 ℃ for 2h at 8-70 ℃ and then at room temperature for 20h824h, the synthetic route is as follows:
Figure BDA0002341194060000101
further, the mass ratio of the compound hexabromo-TCTA to trimethylchlorosilane is 1 (687), and the mass ratio of the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl to trimethylchlorosilane is 1 (283).
In one embodiment, the SUZUKI coupling reaction of the hexabromo-TCTA compound or the 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl with 1-boronic acid cyclohexane comprises the following specific steps: the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl and 1-boracic acid cyclohexane are put in a mixed solvent (toluene/ethanol/pure water) and in palladium (Pd) tetratriphenylphosphine (PPh)3)4Potassium carbonate K2CO3And refluxing and reacting for 10h815h under the condition of nitrogen atmosphere, and the synthetic route is shown as follows.
Figure BDA0002341194060000102
Figure BDA0002341194060000111
Further, the mass ratio of the compound hexabromo-TCTA to cyclohexane-1-borate is 1 (687), and the mass ratio of the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl to cyclohexane-1-borate is 1 (283).
In one embodiment, the preparation steps of the 1-boric acid cyclohexane are as follows: 1-bromocyclohexane and boric acid ester are added into tetrahydrofuran solvent, n-butyllithium is dripped at-80 ℃ and 8-70 ℃ under the atmosphere of nitrogen, the reaction is carried out for 2h83h at-80 ℃ and 8-70 ℃, and then the reaction is carried out for 10h815h at room temperature, and the synthetic route is as follows:
Figure BDA0002341194060000112
in one embodiment, the SUZUKI coupling reaction of the hexabromo-TCTA compound or the 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl with 3-pentane borate comprises the following steps: the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl and 3-pentane borate are mixed in a mixed solvent (toluene/ethanol/pure water) and in palladium tetratriphenylphosphine Pd (PPh)3)4Potassium carbonate K2CO3And carrying out reflux reaction for 10h815h under the condition of nitrogen atmosphere, wherein the synthetic route is as follows:
Figure BDA0002341194060000113
Figure BDA0002341194060000121
further, the mass ratio of the compound hexabromo-TCTA to 3-pentaborate was 1 (687), and the mass ratio of the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl to 3-pentaborate was 1 (283).
In one embodiment, the preparation steps of the 3-pentane borate are as follows: 3-bromopentane and boric acid ester are added into tetrahydrofuran solvent, n-butyl lithium is dripped at-80 ℃ and 8-70 ℃ under the atmosphere of nitrogen, the reaction is carried out for 2h84h at-80 ℃ and 8-70 ℃, and then the reaction is carried out for 10h815h at room temperature, and the synthetic route is as follows:
Figure BDA0002341194060000122
in one embodiment, the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl is subjected to a SUZUKI coupling reaction with 4-boronic acid spirobifluorene, which comprises the following specific steps: the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl and 4-boronic acid spirobifluorene are added in a mixed solvent (toluene/ethanol/pure water) in palladium tetratriphenylphosphine Pd (PPh)3)4Potassium carbonate K2CO3And carrying out reflux reaction for 10h815h under the condition of nitrogen atmosphere, wherein the synthetic route is as follows:
Figure BDA0002341194060000123
Figure BDA0002341194060000131
further, the mass ratio of the compound hexabromo-TCTA to the 4-boronic acid spirobifluorene is 1 (687), or the mass ratio of the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl to the 4-boronic acid spirobifluorene is 1 (283).
In one embodiment, the preparation steps of the 4-boronic acid spirobifluorene are as follows: 4-bromospirobifluorene and boric acid ester are added into tetrahydrofuran solvent, n-butyl lithium is dripped into the tetrahydrofuran solvent under the atmosphere of nitrogen and the temperature of minus 80 ℃ and the temperature of 8 ℃ to 70 ℃, the reaction is carried out for 2h84h at the temperature of minus 80 ℃ and the temperature of 8 ℃ to 70 ℃, and then the reaction is carried out for 10h815h at the room temperature, and the synthetic route is as follows:
Figure BDA0002341194060000132
in one embodiment, the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl is subjected to a SUZUKI coupling reaction with 2-boronic acid-9, 9-diphenylfluorene, which comprises the following specific steps: compound hexabromo-TCTAOr the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl and 2-boric acid-9, 9-diphenylfluorene are mixed in a mixed solvent (toluene/ethanol/pure water) in palladium (Pd) tetratriphenylphosphine (PPh)3)4Potassium carbonate K2CO3And carrying out reflux reaction for 10h815h under the condition of nitrogen atmosphere, wherein the synthetic route is as follows:
Figure BDA0002341194060000141
further, the mass ratio of the compound hexabromo-TCTA to 2-boronic acid-9, 9-diphenylfluorene is 1 (687), and the mass ratio of the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl to 2-boronic acid-9, 9-diphenylfluorene is 1 (283).
In one embodiment, the preparation steps of the 2-boric acid-9, 9-diphenylfluorene are as follows: the preparation method comprises the following steps of putting 2-bromo-9, 9-diphenylfluorene and boric acid ester in a tetrahydrofuran solvent, dropwise adding n-butyllithium in the tetrahydrofuran solvent at-80 ℃ and 8-70 ℃ in a nitrogen atmosphere, reacting at-80 ℃ and 8-70 ℃ for 2h84h, and then reacting at room temperature for 10h815h, wherein the synthetic route is as follows:
Figure BDA0002341194060000142
in one embodiment, the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl is subjected to a SUZUKI coupling reaction with 1- (4-boranophenyl) -1,2, 2-triphenylethylene, which comprises the following specific steps: the compound hexabromo-TCTA or the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl and 1- (4-boranophenyl) -1,2, 2-triphenylethylene are mixed in a mixed solvent (toluene/ethanol/pure water) in palladium (Pd) tetratriphenylphosphine (PPh)3)4Potassium carbonate K2CO3And carrying out reflux reaction for 10h815h under the condition of nitrogen atmosphere, wherein the synthetic route is as follows:
Figure BDA0002341194060000151
further, the mass ratio of the compound hexabromo-TCTA to 1- (4-boranophenyl) -1,2, 2-triphenylethylene was 1 (687), and the mass ratio of the compound 4,4 '-bis (3-bromo-9H-carbazol-9-yl) -1,1' -biphenyl to 1- (4-boranophenyl) -1,2, 2-triphenylethylene was 1 (283).
In one embodiment, the preparation steps of the 1- (4-boraphenyl) -1,2, 2-triphenylethylene are as follows: 1- (4-bromophenyl) -1,2, 2-triphenylethylene and boric acid ester are added into tetrahydrofuran solvent, n-butyllithium is dripped at-80 ℃ and 8-70 ℃ under the atmosphere of nitrogen, the mixture reacts at-80 ℃ and 8-70 ℃ for 2h84h, and then the mixture reacts at room temperature for 10h815h, and the synthetic route is as follows:
Figure BDA0002341194060000161
it is understood that the reaction of the above compounds may further comprise the steps of isolation, purification and drying, and the specific isolation, purification and drying manner may be performed by the conventional operation in the art.
The invention also provides a composition comprising an electron donor compound as defined in any of the above or obtained by the above process, and at least one organic solvent.
The invention also provides the application of any electron donor compound or the electron donor compound prepared by the preparation method or the composition in preparing a light-emitting device.
The invention provides a light-emitting device which comprises an electron donor molecule, wherein the electron donor molecule structurally comprises trimethylsilyl, cyclohexyl, 3-pentyl, 4- (9,9' -spirobifluorene) group, 2- (9, 9-diphenylfluorene) group or tetraphenylvinyl.
The light-emitting device comprises the electron donor molecule, the electron donor molecule structurally comprises the substituent, the substituent has a steric hindrance effect and is shown as an insulating property, so that when the electron donor molecule is used as an electron donor material in an interface heterojunction exciplex system, the contact point of an original electron donor and an original electron acceptor is isolated by a non-hydrogen substituent, electrons and holes are separated in space, electrons of the electron acceptor layer can be prevented or hindered from easily moving into the electron donor layer, the charging problem of quantum dots is avoided or relieved, and the efficiency and the service life of the light-emitting device are improved.
In some embodiments, the electron donor molecule is an electron donor compound as described above or an electron donor compound prepared by the preparation methods described above.
Referring to fig. 1, in some embodiments, the light emitting device 100 includes a substrate 110, which may be made of any material and disposed in any manner known in the art, and is not limited herein. Specifically, the substrate 110 may be a common rigid substrate such as glass, a common flexible substrate such as PI film, or the like.
In some embodiments, the light emitting device further includes an electron donor layer 120, and the electron donor layer 120 contains the electron donor molecules described above.
In some embodiments, the light emitting device 100 further includes an electron acceptor layer 130, the electron acceptor layer 130 being in direct contact with the electron donor layer 120, the electron donor layer 120 and the electron acceptor layer 130 being capable of forming an interfacial heterojunction exciplex therebetween.
The exciplex enlarges the space distance of electron holes, forms long-range exciplex excitons, and enables electrons to be far away from quantum dots, thereby effectively avoiding the electrons from being captured by the quantum dots.
According to the theory of organic electronics: in a bimolecular exciplex system, appropriate spatial separation of electrons and holes can reduce the overlapping degree of HOMO and LUMO, so that the singlet-triplet energy level difference (delta Est) is reduced, which is beneficial to improving the efficiency of exciplex excitons converted from triplet state to singlet state, further reducing the probability of triplet exciton annihilation and improving the efficiency of exciplex excitons transferred to quantum dots.
The exciton energy of the exciplex is required to be smaller than the exciton energy of the electron donor molecule and the electron acceptor molecule which form the exciplex system, so that the exciplex excitons are limited in the exciplex system, and the exciplex excitons are prevented from being separated due to the action of an electric field.
The exciton energy of the exciplex is controlled to be larger than that of the quantum dot, and the emission spectrum of the exciplex exciton and the absorption spectrum of the quantum dot are obviously overlapped at the first exciton absorption peak of the quantum dot, so that the quantum dot can fully absorb the exciton energy of the exciplex, the energy transfer efficiency can be maximized, and the efficient quantum dot light emission and the high light emission purity can be obtained.
In one embodiment, the electron donor layer 120 further includes a quantum dot material mixed with the electron donor molecules. In this way, the electron donor layer 120 simultaneously functions as a light emitting layer, and the quantum dots are doped in the electron donor layer, so that electrons in the electron acceptor layer can be effectively prevented from being captured by the quantum dots.
Further, the quantum dot material may be a II-VI compound semiconductor, such as: CdSe, ZnCdS, CdSeS, ZnCdSeS, CdSe/ZnS, CdSeS/ZnS, CdSe/CdS/ZnS, ZnCdS/ZnS, CdS/ZnS, ZnCdSeS/ZnS, etc.; may be a group III-V compound semiconductor, for example: InP, InP/ZnS, etc.; may be a group I-III-VI compound semiconductor, for example: CuInS, AgInS, CuInS/ZnS, AnInS/ZnS, etc.; can be a group IV elementary semiconductor, such as Si or C or Graphene, and the like; may be perovskite quantum dots, etc.
Further, the material of the electron acceptor layer 130 is selected from at least one of 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline, and tris (2,4, 6-trimethyl-3- (pyridin-3-yl) phenyl) borane.
In one embodiment, the light emitting device further includes an anode 140 and a cathode 150, the anode 140 being disposed on a side of the electron donor layer 120 away from the electron acceptor layer 130, and the cathode 150 being disposed on a side of the electron acceptor layer 130 away from the electron donor layer 120.
It is understood that in one embodiment, the anode 140 is disposed on the substrate 110, the electron donor layer 120 and the electron acceptor layer 130 are sequentially disposed on the anode 140, and the cathode 150 is disposed on the electron acceptor layer 130, as shown in fig. 1. In another specific example, the cathode may be provided on the substrate, the electron acceptor layer and the electron donor layer may be provided on the cathode in this order, and the anode may be provided on the electron donor layer.
In an embodiment, the light emitting device further includes a hole injection layer 160 disposed between the anode 140 and the electron donor layer 120, and a hole transport layer 170 disposed between the hole injection layer 160 and the electron donor layer 120.
Further, the material of the hole injection layer 160 may be a conductive polymer, such as: PEDOT: PSS; it may also be a high work function n-type semiconductor, such as: HAT-CN, MoO3、WO3、V2O5、Rb2O, and the like.
Further, the hole transport layer 170 may be an organic hole transport layer, such as: Poly-TPD, TFB, PVK, 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 4' -bis (9-Carbazol) Biphenyl (CBP), NPB, NPD, etc.; or an inorganic hole transport layer, e.g. NiO, Cu2O, and the like.
In one embodiment, the electron donor layer 120 is disposed between the hole transport layer 170 and the cathode 150, the electron acceptor layer 130 is disposed between the electron donor layer 120 and the cathode 150,
in one embodiment, the light emitting device 100 further includes an electron transport layer 180 disposed between the electron acceptor layer 130 and the cathode 150, and an electron injection layer 190 disposed between the electron transport layer 180 and the cathode 150.
Further, the material of the electron transport layer 180 may be 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), TmPyPb, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), Bphen, TmPyTz, tris (2,4, 6-trimethyl-3- (pyridin-3-yl) phenyl) borane (3TPYMB), 4, 6-bis (3, 5-bis (pyridin-3-yl) phenyl) -2-methyl (B3PYMPM), 1, 3-dicarbazole-9-ylbenzene (PO-T2T), or the like.
Further, the material of the electron injection layer 190 may be an alkali metal salt, for example: LiF, NaF, CsF, Cs2CO3Etc.; may be a low work function metal such as: mg, Yb, Ba, etc.
The present invention also provides a display device including any one of the above light emitting devices.
It is understood that the display device may be a mobile phone, a computer, a tablet, a television, or the like for displaying.
The following are specific examples
Example 1812 is an example of the synthesis of an electron donor compound.
Example 1
Sequentially adding 2mmol of hexabromo-TCTA into a 150mL two-neck bottle, adding 80mL of tetrahydrofuran solvent subjected to water removal and oxygen removal under the nitrogen atmosphere, uniformly stirring, placing the mixture at-78 ℃, dropwise adding 12.5mmol of n-butyllithium, reacting at-78 ℃ for 3h, adding 13mmol of trimethylchlorosilane, reacting at-78 ℃ for 2h, recovering to room temperature, reacting for 24h, pouring the reaction solution into water after the reaction is finished, extracting for 3 times by using dichloromethane, and then using anhydrous MgSO (MgSO)4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating with n-hexane/dichloromethane as eluent to remove solvent to obtain tris (4- (3, 6-bis (trimethylsilyl) -9H-carbazol-9-yl) phenyl) amine (compound M1). The yield was 42%, and HPLC-MS was used to identify this compound, formula C69H78N4Si6Detection value [ M +1 ]]+1131.62, calculate value 1130.48.
Example 2
Sequentially adding 2mmol of 4,4 '-bis (3-bromo-9H-carbazole-9-yl) -1,1' -biphenyl into a 150mL two-neck flask, adding 80mL of tetrahydrofuran solvent subjected to water removal and oxygen removal under the atmosphere of nitrogen, uniformly stirring, placing the mixture at-78 ℃, then dropwise adding 4.5mmol of n-butyllithium, reacting at-78 ℃ for 3 hours, then adding 13mmol of 5mmol of trimethylchlorosilane, reacting at-78 ℃ for 2 hours, then returning to room temperature for reaction for 24 hours, pouring the reaction solution into water after the reaction is completed, extracting for 3 times by using dichloromethane, and then using anhydrous MgSO4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating with n-hexane/dichloromethane as eluent to remove solvent to obtain 4,4 '-bis (3- (trimethylsilyl) -9H-carbazol-9-yl) -1,1' -biphenyl (compound M7) with a yield of 56%. This compound, formula C, was identified using HPLC-MS42H40N2Si2Detection value [ M +1 ]]+629.58, calculate value 628.27.
Example 3
Sequentially adding 5mmol of 1-bromocyclohexane into a 150mL two-neck flask, adding 80mL of tetrahydrofuran solvent (THF) subjected to water removal and oxygen removal under the atmosphere of nitrogen, then adding 5.5mmol of boric acid ester, uniformly stirring, placing at-78 ℃, then dropwise adding 5.1mmol of n-butyllithium, reacting at-78 ℃ for 3h, then returning to room temperature for reaction for 12h, pouring the reaction solution into water after the reaction is finished, extracting for 3 times by using dichloromethane, and then using anhydrous MgSO4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating and drying to remove solvent with n-hexane/dichloromethane as eluent to obtain 1-boric acid cyclohexane with yield of 51%. HPLC-MS was used to identify these two compounds, formula C6H13BO2Detection value [ M +1 ]]+129.42, calculate value 128.10.
In a 150mL two-neck flask are sequentially added 6mmol of 1-cyclohexane borate, 1mmol of hexabromo-TCTA and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh)3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying by using a silica gel chromatographic column, collecting a product by using n-hexane/dichloromethane as an eluent by rotary evaporation to remove the solvent, and finally obtaining the compound tris (4- (3, 6-dicyclohexyl-9H-carbazole-9-yl) phenyl) amine (compound M2) with the separation yield of 45%. The compound, formula C, was identified using HPLC-MS90H96N4Detection value [ M +1 ]]+1233.54, calculate value 1232.76.
Example 4
Sequentially adding 6mmol of 1-cyclohexane borate, 3mmol of 4,4 '-bis (3-bromo-9H-carbazole-9-yl) -1,1' -biphenyl and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding a mixed solvent of toluene/ethanol/pure water (V/V/V is 8:1:1)8 under the nitrogen atmosphere0ml, and then refluxing and reacting for 12 hours; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, collecting product by rotary evaporation with n-hexane/dichloromethane as eluent, and obtaining compound 4,4 '-bis (3-cyclohexyl-9H-carbazol-9-yl) -1,1' -biphenyl (compound M8) with separation yield of 53%, which is identified by HPLC-MS with molecular formula C48H44N2Detection value [ M +1 ]]+649.67, calculate value 648.35.
Example 5
Sequentially adding 5mmol of 3-bromopentane into a 150mL two-neck flask, adding 80mL of tetrahydrofuran solvent (THF) subjected to water removal and oxygen removal under the atmosphere of nitrogen, then adding 5.5mmol of boric acid ester, uniformly stirring, placing at-78 ℃, then dropwise adding 5.1mmol of n-butyllithium, reacting at-78 ℃ for 3h, then returning to room temperature for reaction for 12h, pouring the reaction solution into water after the reaction is finished, extracting for 3 times by using dichloromethane, and then using anhydrous MgSO (MgSO)4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating and drying to remove solvent with n-hexane/dichloromethane as eluent to obtain 3-pentane borate with yield of 62%. The compound, formula C, was identified using HPLC-MS5H13BO2Detection value [ M +1 ]]+117.63, calculate value 116.10.
In a 150mL two-mouth bottle, 6mmol of 3-pentane borate, 1mmol of hexabromo-TCTA and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) are sequentially added3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, eluting with n-hexane/dichloromethane, collecting product by rotary evaporation to obtainThe compound tris (4- (3, 6-bis (pent-3-yl) -9H-carbazol-9-yl) phenyl) amine (compound M3) was isolated in 52% yield. The compound, formula C, was identified using HPLC-MS84H96N4Detection value [ M +1 ]]+1161.86, calculate value 1160.76.
Example 6
Sequentially adding 6mmol of 3-pentane borate, 3mmol of 4,4 '-bis (3-bromo-9H-carbazole-9-yl) -1,1' -biphenyl and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, collecting product by rotary evaporation with n-hexane/dichloromethane as eluent, to obtain compound 4,4 '-bis (3- (pent-3-yl) -9H-carbazol-9-yl) -1,1' -biphenyl (compound M9) with separation yield of 61%, identifying the compound with molecular formula C by HPLC-MS46H44N2Detection value [ M +1 ]]+625.69, calculate value 624.35.
Example 7
Sequentially adding 5mmol of 4-bromospirobifluorene into a 150mL two-neck flask, adding 80mL of tetrahydrofuran solvent (THF) subjected to water removal and oxygen removal under the atmosphere of nitrogen, then adding 5.5mmol of boric acid ester, uniformly stirring, placing the mixture at-78 ℃, then dropwise adding 5.1mmol of n-butyl lithium, reacting for 3h at-78 ℃, then returning to room temperature for reacting for 12h, pouring the reaction liquid into water after the reaction is finished, extracting for 3 times by using dichloromethane, and then using anhydrous MgSO4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating with n-hexane/dichloromethane as eluent to remove solvent to obtain 4-spirobifluorene borate with yield of 33%. The compound, formula C, was identified using HPLC-MS25H17BO2Detecting value [ M +1 ]]+361.41, calculate 360.13.
6mmol of 4-spirobifluorene borate, 1mmol of hexabromo-TCTA and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) are sequentially added into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing the solvent by rotary evaporation, separating and purifying by using a silica gel chromatographic column, collecting the product by rotary evaporation by using normal hexane/dichloromethane as an eluent, and finally obtaining the compound tris (4- (3, 6-bis (4- (9,9' -spirobifluorene) yl) -9H-carbazol-9-yl) phenyl) amine (compound M4) with the separation yield of 32%. The compound, formula C, was identified using HPLC-MS204H120N4Detecting value [ M +1 ]]+2625.86, calculate value 2624.95.
Example 8
6mmol of 4-boric acid spirobifluorene, 3mmol of 4,4 '-bis (3-bromo-9H-carbazole-9-yl) -1,1' -biphenyl and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) are sequentially added into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing the solvent by rotary evaporation, separating and purifying by using a silica gel chromatographic column, collecting the product by rotary evaporation by using normal hexane/dichloromethane as an eluent, and finally obtaining the compound 4,4' -bis (3- (9,9' -spirobifluoren-4-yl) -9H-carbazol-9-yl) -1,1' -biphenyl (compound M10) with the separation yield of 58%. The compound, formula C, was identified using HPLC-MS86H52N2Detecting value [ M +1 ]]+1113.62, calculate value 1112.41.
Example 9
Adding 5mmol of 2-bromo-9, 9-diphenylfluorene into a 150mL two-mouth bottle in sequence, and adding the mixture under the nitrogen atmosphereAdding 80mL of tetrahydrofuran solvent (THF) after water and oxygen removal, then adding 5.5mmol of boric acid ester, uniformly stirring, placing the mixture at-78 ℃, then dropwise adding 5.1mmol of n-butyllithium, reacting at-78 ℃ for 3h, then returning to room temperature for reaction for 12h, pouring the reaction solution into water after the reaction is finished, extracting with dichloromethane for 3 times, and then using anhydrous MgSO4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating with n-hexane/dichloromethane as eluent to remove solvent to obtain 2-boric acid-9, 9-diphenylfluorene with yield of 78%. The compound, formula C, was identified using HPLC-MS25H19BO2Detecting value [ M +1 ]]+363.38, calculate value 362.14.
6mmol of 2-boric acid-9, 9-diphenylfluorene, 1mmol of hexabromo-TCTA and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) are sequentially added into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, collecting product by rotary evaporation with n-hexane/dichloromethane as eluent, and obtaining compound tris (4- (3, 6-bis (2- (9, 9-diphenyl-9H-fluorene) yl) -9H-carbazol-9-yl) phenyl) amine (compound M5) with separation yield of 32%, which is identified by HPLC-MS with molecular formula C204H132N4Detecting value [ M +1 ]]+2638.23, calculate value 2637.04.
Example 10
Sequentially adding 6mmol of 2-boric acid-9, 9-diphenylfluorene, 3mmol of 4,4 '-bis (3-bromo-9H-carbazole-9-yl) -1,1' -biphenyl and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after the reaction is finished, cooling to room temperature, pouring the reaction liquid into waterIn the reaction solution, the mixture was extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, collecting product by rotary evaporation with n-hexane/dichloromethane as eluent to obtain compound 4,4 '-bis (3- (9, 9-diphenyl-9H-fluoren-2-yl) -9H-carbazol-9-yl) -1,1' -biphenyl (compound M11) with separation yield of 43%, and identifying the compound with molecular formula C by HPLC-MS86H56N2Detecting value [ M +1 ]]+1117.83, calculate value 1116.44.
Example 11
Adding 5mmol of 1- (4-bromophenyl) -1,2, 2-triphenylethylene into a 150mL two-neck flask in sequence, adding 80mL of tetrahydrofuran solvent (THF) obtained after water and oxygen removal under nitrogen atmosphere, then adding 5.5mmol of boric acid ester, uniformly stirring, placing the mixture at-78 ℃, then dropwise adding 5.1mmol of n-butyllithium, reacting at-78 ℃ for 3h, then returning to room temperature for reaction for 12h, pouring the reaction solution into water after the reaction is completed, extracting with dichloromethane for 3 times, and then using anhydrous MgSO4Drying, filtering, rotary evaporating to remove solvent, separating and purifying with silica gel chromatographic column, and rotary evaporating with n-hexane/dichloromethane as eluent to remove solvent to obtain 1- (4-boraphenyl) -1,2, 2-triphenylethylene with yield of 69%. The compound, formula C, was identified using HPLC-MS26H21BO2Detecting value [ M +1 ]]+377.46, calculate value 376.16.
6mmol of 2-boric acid-9, 9-diphenylfluorene, 1mmol of hexabromo-TCTA and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) are sequentially added into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, eluting with n-hexane/dichloromethane, collecting product by rotary evaporation to obtain the final productThe compound tris (4- (3, 6-bis (4- (1,2, 2-triphenylvinyl) phenyl) -9H-carbazol-9-yl) phenyl) amine (compound M6) was isolated in 32% yield and was identified using HPLC-MS, formula C210H144N4Detecting value [ M +1 ]]+2722.35, calculate value 2721.14.
Example 12
Sequentially adding 6mmol of 2-boric acid-9, 9-diphenylfluorene, 3mmol of 4,4 '-bis (3-bromo-9H-carbazole-9-yl) -1,1' -biphenyl and 0.1mmol of tetratriphenylphosphine palladium Pd (PPh) into a 150mL two-mouth bottle3)44mmol of potassium carbonate K2CO3Adding 80ml of mixed solvent toluene/ethanol/pure water (V/V/V is 8:1:1) under the nitrogen atmosphere, and then carrying out reflux reaction for 12 h; after completion of the reaction, the reaction mixture was cooled to room temperature, poured into water, extracted with dichloromethane 3 times, and the organic layer was successively washed with concentrated brine and pure water, and then with anhydrous MgSO4Drying, filtering, removing solvent by rotary evaporation, separating and purifying with silica gel chromatographic column, collecting product by rotary evaporation with n-hexane/dichloromethane as eluent, to obtain 4,4 '-bis (3- (4- (1,2, 2-triphenylvinyl) phenyl) -9H-carbazol-9-yl) -1,1' -biphenyl (compound M12) with separation yield of 54%, and identifying the compound with HPLC-MS (molecular formula C)88H60N2Detecting value [ M +1 ]]+1145.73, calculate value 1144.48.
Embodiment 13821 is an example of a light-emitting device.
Example 13
The transparent conductive film ITO is used as an anode, and the thickness is 50 nm.
PSS as a hole injection layer with a thickness of 30nm was deposited on the anode using a solution method.
TFB was deposited as a hole transport layer on the hole injection layer using a solution method to a thickness of 30 nm.
A compound M7: CdZnSe/ZnSe (mass ratio: 8:2) as an electron donor layer was deposited on the hole transport layer by a solution method to a thickness of 40 nm.
B3PYMPM was deposited as an electron acceptor layer on the electron donor layer by an evaporation method to a thickness of 30 nm.
B3PYMPM was deposited as an electron transport layer on the electron acceptor layer by evaporation to a thickness of 30 nm.
Liq was deposited as an electron injection layer on the electron transport layer by evaporation to a thickness of 2 nm.
And depositing Al on the electron injection layer by using an evaporation method to be used as a cathode, wherein the thickness of the Al is 120nm, and thus obtaining the light-emitting device.
Example 14
The light-emitting device of example 14 was produced in a similar manner to example 13 except that: the compound M7: CdZnSe/ZnSe (mass ratio: 7:3) as an electron donor layer.
Example 15
The light-emitting device of example 15 was produced in a similar manner to example 13 except that: the compound M7: CdZnSe/ZnSe (mass ratio 6:4) as an electron donor layer.
Example 16
The light-emitting device of example 16 was produced in a similar manner to example 13 except that: the compound M7: CdZnSe/ZnSe (mass ratio 5:5) as an electron donor layer.
Example 17
A light-emitting device of example 17 was produced in a similar manner to example 13 except that: the compound M3: ZnCdSe/ZnSe (mass ratio 7:3) as an electron donor layer.
Example 18
A light-emitting device of example 18 was produced in a similar manner to example 13 except that: the compound M4: ZnCdSe/ZnSe (mass ratio 7:3) as an electron donor layer.
Example 19
The light-emitting device of example 19 was produced in a similar manner to example 13 except that: the compound M6: ZnCdSe/ZnSe (mass ratio 7:3) as an electron donor layer.
Example 20
The light-emitting device of this example 20 was produced in a similar manner to example 13 except that: the compound M8: ZnCdSe/ZnSe (mass ratio 7:3) as an electron donor layer.
Example 21
A light-emitting device of example 21 was produced in a similar manner to example 13 except that: the compound M10: ZnCdSe/ZnSe (mass ratio 7:3) as an electron donor layer.
Performance testing
The light-emitting device prepared in example 13821 was tested, and the test results are shown in table 1:
TABLE 1
Item Maximum external quantum efficiency EQE Life LT95@1000nits (h)
Example 13 10.2％ 2120
Example 14 12.5％ 2843
Example 15 11.4％ 2551
Example 16 10.8％ 2368
Example 17 12.9％ 2745
Example 18 14.2％ 2957
Example 19 13.8％ 2888
Example 20 12.7％ 2752
Example 21 13.4％ 2644
LT95 time taken for the device to drop from 1000nit to 95% brightness (i.e., 950nit) by illuminating the device with a constant current and adjusting the brightness of the device to 1000 nit.
External quantum efficiency: the ratio of the number of photons emitted from the device to the number of electrons injected into the device is numerically equal, and the photoelectric conversion efficiency of the device is represented and can be obtained by testing of a special testing system.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (14)

1. An electron donor compound characterized by having a group of the structure shown below:
Figure FDA0002341194050000011
each R is1Independently selected from hydrogen, trimethylsilyl, cyclohexyl, 3-pentyl, 4- (9,9' -spirobifluorene) yl, 2- (9, 9-diphenylfluorene) yl or tetraphenylvinyl; and each R1Not hydrogen at the same time.
2. The electron donor compound according to claim 1, characterized in that it has the general structural formula shown in formula (I):
Figure FDA0002341194050000012
wherein L is a single bond or
Figure FDA0002341194050000013
3. Electron donor compound according to claim 2, characterized in that it has a general formula as shown in formula (Ia) or formula (Ib):
Figure FDA0002341194050000021
4. the electron donor compound according to claim 1, characterized in that it is selected from one of the following compounds M1-M12:
Figure FDA0002341194050000022
Figure FDA0002341194050000031
5. a process for the preparation of an electron donor compound, comprising the steps of:
a compound of formula (II) and a compound containing R1The compound of the group is prepared by coupling reaction; said compound containing R1The compound of the group is trimethyl chlorosilane, 1-cyclohexane borate, 3-pentane borate, 4-spirobifluorene borate, 2-9, 9-diphenylfluorene borate or 1- (4-phenyl borate) -1,2, 2-triphenylethylene;
the general formula of the compound shown in the formula (II) is as follows:
Figure FDA0002341194050000032
wherein L is a single bond or
Figure FDA0002341194050000033
Each R is2Independently selected from hydrogen or halogen groups.
6. Composition comprising an electron donor compound according to any one of claims 1 to 4 or obtained by a process according to claim 5, and at least one organic solvent.
7. Use of an electron donor compound according to any one of claims 1 to 4, or an electron donor compound obtained by the preparation process according to claim 5, or a composition according to claim 6, for the preparation of a light-emitting device.
8. A light-emitting device comprising an electron donor molecule having a structure comprising a trimethylsilyl group, a cyclohexyl group, a 3-pentyl group, a 4- (9,9' -spirobifluorene) group, a 2- (9, 9-diphenylfluorene) group or a tetraphenylvinyl group.
9. The light-emitting device according to claim 8, wherein the electron donor molecule is the electron donor compound according to any one of claims 1 to 4 or the electron donor compound obtained by the preparation method according to claim 5.
10. The light-emitting device according to claim 8, further comprising an electron donor layer containing the electron donor molecule.
11. A light emitting device in accordance with claim 10, further comprising an electron acceptor layer in direct contact with the electron donor layer, wherein an interfacial heterojunction exciplex can be formed between the electron donor layer and the electron acceptor layer.
12. A light emitting device according to claim 10 or 11, wherein the electron donor layer further comprises a quantum dot material intermixed with the electron donor molecules.
13. A light-emitting device according to claim 11, wherein the material of the electron acceptor layer is at least one selected from the group consisting of 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline and tris (2,4, 6-trimethyl-3- (pyridin-3-yl) phenyl) borane.
14. A display device comprising the light-emitting device according to any one of claims 8 to 13.
CN201911376831.8A 2019-12-27 2019-12-27 Electron donor compound, method for producing the same, light-emitting device, and display device Pending CN112321630A (en)

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