CN110964009B - Compound containing phenanthroline structure, application thereof and organic electroluminescent device - Google Patents

Compound containing phenanthroline structure, application thereof and organic electroluminescent device Download PDF

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CN110964009B
CN110964009B CN201911176899.1A CN201911176899A CN110964009B CN 110964009 B CN110964009 B CN 110964009B CN 201911176899 A CN201911176899 A CN 201911176899A CN 110964009 B CN110964009 B CN 110964009B
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organic electroluminescent
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吕瑶
冯美娟
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Beijing Green Guardee Technology Co ltd
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Abstract

The invention relates to the field of organic electroluminescent devices, and discloses a compound containing a phenanthroline structure, application thereof and an organic electroluminescent device, wherein the compound has a structure shown in a formula (I). The compound of the invention can obviously reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency and prolong the service life.

Description

Compound containing phenanthroline structure, application thereof and organic electroluminescent device
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to a compound containing a phenanthroline structure, application of the compound in an organic electroluminescent device and an organic electroluminescent device containing the compound.
Background
The organic electroluminescence phenomenon is discovered by Pope et al in 1963, and the organic electroluminescence phenomenon is discovered by the Pope et al, and the single-layer crystal of anthracene can emit weak blue light under the driving of a voltage of more than 100V, but the driving voltage is high, the thickness of single-crystal anthracene is large, and the single-layer crystal of anthracene does not attract wide attention of people. Until 1987, Dungqing cloud Boshi of Kodak company reported that based on two organic semiconductor materials of 8-hydroxyquinoline aluminum with high fluorescence efficiency and good electron transport property and aromatic diamine with good hole transport property, the device is a sandwich type OLED prepared by vacuum thermal evaporation, and under the voltage that the driving voltage is less than 10V, the external quantum efficiency reaches 1%, so that the organic electroluminescent material and the device have the possibility of practicability, and the research on the OLED material and the device is greatly promoted.
With the continuous development of the OLED technology, the performance of the OLED device is also widely concerned, and in the research process, it is found that a device with high efficiency, long service life and excellent performance needs excellent device materials and matching among various layers of the device.
The principle of organic electroluminescence is to convert electric energy into light energy by using organic substances, and a common organic light-emitting element generally comprises a cathode and an anode and a structure of an organic layer between the cathode and the anode, wherein the organic layer mainly comprises a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material and the like.
In the organic electroluminescent device, the conventional electron transport layer material Alq3Has low electron mobility, and makes carrier recombination unbalanced.
In order to obtain a high-performance electron transport material, the material is required to have high electron mobility so as to improve the light emission efficiency and the lifetime of the device.
The working principle of the solar cell relates to the absorption of photons and the generation process of excitons, the injection and transmission process of electrons and holes to an electron and hole transport layer respectively, and the collection process of electrodes. Among them, the electron transport material is required to have a high electron mobility to improve the device efficiency.
Disclosure of Invention
The invention aims to overcome the defects of high driving voltage, low luminous efficiency and short service life of the organic electroluminescent device in the prior art.
In order to achieve the above objects, the first aspect of the present invention provides a phenanthroline-containing structure-containing compound having a structure represented by formula (I),
Figure BDA0002290195040000021
wherein, in the formula (I),
a is a structure represented by formula (II), and in formula (II), X is O or S;
L1is absent or L1Is phenyl represented by formula (III);
L2is absent fromOr L2Is phenyl represented by formula (III);
X1、X2and X3Each independently selected from N and C, and X1、X2And X3At least two of which are N;
R1and R2Each independently selected from phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, fluorenyl represented by formula (IV).
A second aspect of the present invention provides the use of a compound according to the first aspect as hereinbefore described in an organic electroluminescent device.
A third aspect of the present invention provides an organic electroluminescent device comprising the compound of the first aspect, which is present in at least one of an electron transporting layer, a light-emitting layer and a hole blocking layer of the organic electroluminescent device.
The compound provided by the invention has proper HOMO energy level and LUMO energy level, wherein the HOMO energy level and the LUMO energy level are relatively deep, the deep HOMO energy level can block holes, and the deep LUMO energy level is beneficial to the injection of electrons.
Meanwhile, the compound of the invention can realize the adjustment of the LUMO energy level in a small range, so that the matching degree of the LUMO energy level of the compound and the LUMO energy level of a light-emitting layer is high, and the driving voltage of an organic electroluminescent device is reduced.
In addition, the compound of the present invention has high electron mobility and thus high electron transport capacity. Therefore, when the compound is applied to an organic electroluminescent device, the recombination capability of carriers can be improved, so that the luminous efficiency of the organic electroluminescent device is improved. Meanwhile, when the compound is applied to a solar cell, the efficiency of the device can be improved.
Furthermore, the compound has higher glass transition temperature, so that the thermal stability of the film is good, and the service life of the organic electroluminescent device is prolonged.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
As described above, the first aspect of the present invention provides a phenanthroline-containing compound having a structure represented by formula (I),
Figure BDA0002290195040000041
wherein, in the formula (I),
a is a structure represented by formula (II), and in formula (II), X is O or S;
L1is absent or L1Is phenyl represented by formula (III);
L2is absent or L2Is phenyl represented by formula (III);
X1、X2and X3Each independently selected from N and C, and X1、X2And X3At least two of which are N;
R1and R2Each independently selected from phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, fluorenyl represented by formula (IV).
Preferably, in formula (I), R1And R2Each independently selected from the group consisting of:
Figure BDA0002290195040000042
Figure BDA0002290195040000051
more preferably, in formula (I), R1And R2Identical and selected from the following groups:
Figure BDA0002290195040000052
Figure BDA0002290195040000061
several preferred embodiments of the compounds of the present invention are provided below.
Embodiment mode 1:
in the formula (I), the compound represented by the formula (I),
a is a structure represented by formula (II), and in formula (II), X is O or S;
L1is absent or L1Is phenyl represented by formula (III);
L2is absent or L2Is phenyl represented by formula (III);
X1、X2and X3Are all N;
R1and R2Each independently selected from phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, fluorenyl represented by formula (IV).
Embodiment mode 2:
in the formula (I), the compound represented by the formula (I),
a is a structure represented by formula (II), and in formula (II), X is O or S;
L1is absent or L1Is phenyl represented by formula (III);
L2is absent or L2Is phenyl represented by formula (III);
X1、X2and X3Are all N;
R1and R2And the same or different and is selected from phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, fluorenyl represented by formula (IV).
Embodiment mode 3:
in the formula (I), the compound represented by the formula (I),
a is a structure represented by formula (II), and in formula (II), X is O or S;
L1is absent or L1Is phenyl represented by formula (III);
L2is absent or L2Is phenyl represented by formula (III);
X1、X2and X3Any two of which are N, and the remaining one is C;
R1and R2Each independently selected from phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, fluorenyl represented by formula (IV).
Embodiment 4:
in the formula (I), the compound represented by the formula (I),
a is a structure represented by formula (II), and in formula (II), X is O or S;
L1is absent or L1Is phenyl represented by formula (III);
L2is absent or L2Is phenyl represented by formula (III);
X1、X2and X3Any two of which are N, and the remaining one is C;
R1and R2And the same or different and is selected from phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, fluorenyl represented by formula (IV).
Embodiment 5:
the compound with the structure shown in the formula (I) is selected from at least one of the following compounds:
Figure BDA0002290195040000071
Figure BDA0002290195040000081
Figure BDA0002290195040000091
embodiment 6:
the compound with the structure shown in the formula (I) is selected from at least one of the following compounds:
Figure BDA0002290195040000092
the present invention is not particularly limited to the preparation method of the compound having the structure represented by formula (I), and those skilled in the art can determine an appropriate synthesis method according to the structural formula of the compound provided by the present invention in combination with the preparation method of the preparation example.
Further, the preparation examples of the present invention are given as examples of the preparation methods of some compounds, and those skilled in the art can obtain all the compounds of the present invention according to the preparation methods of these examples. The present invention will not be described in detail herein with respect to specific methods of preparing the various compounds of the present invention, which should not be construed as limiting the invention to those skilled in the art.
As mentioned above, the second aspect of the present invention provides the use of a compound according to the first aspect in an organic electroluminescent device.
According to a preferred embodiment, the present invention provides an organic electroluminescent device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the one or more organic material layers comprise a compound of the present invention.
In the present invention, one of the first electrode and the second electrode is an anode, and the other is a cathode.
According to a preferred embodiment of the present invention, the organic electroluminescent device of the present invention includes a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron injection layer, and the like as the organic material layer.
Particularly preferably, as described above, the third aspect of the present invention provides an organic electroluminescent device comprising the compound according to the first aspect, the compound being present in at least one of an electron transporting layer, a light-emitting layer and a hole blocking layer of the organic electroluminescent device.
Particularly preferably, the compound is present in an electron transport layer and/or a hole blocking layer of the organic electroluminescent device.
The compound is further preferably used as an electron transport material in an electron transport layer of the organic electroluminescent device.
The inventor of the invention finds that when the compound is used as an electron transport material in an electron transport layer of an organic electroluminescent device, the driving voltage of the organic electroluminescent device can be obviously reduced, the luminous efficiency is improved, and the service life is prolonged.
According to a preferred embodiment of the present invention, the organic electroluminescent device further comprises a cover layer disposed on the outer surface of the cathode, wherein the cover layer comprises at least one compound of the present invention.
The organic electroluminescent device of the invention is preferably coated in one layer or in a plurality of layers by means of a sublimation process. In this case, in the vacuum sublimation system, the temperature is less than 10 DEG-3Pa, preferably less than 10-6The compound provided by the present invention is applied by vapor deposition at an initial pressure of Pa.
The organic electroluminescent device according to the invention is also preferably coated with one or more layers by an organic vapor deposition method or sublimation with the aid of a carrier gas. In this case, 10-6Applying the compound at a pressure of Pa to 100 Pa. A particular example of such a process is an organic vapor deposition jet printing process, wherein the compounds provided by the present invention are applied directly through a nozzle and form a device structure.
The organic electroluminescent device according to the invention is preferably prepared by formulating the compounds according to the invention in solution to form a layer or a layer structure by spin coating or by means of any printing means, such as screen printing, flexographic printing, ink-jet printing, lithographic printing, more preferably photo-induced thermal imaging or ink-jet printing. In general, when a plurality of layers are manufactured by the method, the damage between the layers is easy to occur, namely when one layer is manufactured and another layer is manufactured by using a solution, the formed layer can be damaged by a solvent in the solution, and the manufacture of the organic electroluminescent device is not facilitated. However, the compounds provided by the present invention are capable of undergoing crosslinking upon heating or ultraviolet exposure, thereby maintaining an intact layer without being damaged. The compounds according to the invention can additionally be applied from solution and fixed in the respective layer by subsequent crosslinking in the polymer network.
The organic electroluminescent device of the invention can be produced as a mixed system by solution application of one or more layers and by vapor deposition application of one or more further layers.
According to some embodiments of the invention, the anode material forming the anode, generally preferred is a material with a large work function, e.g. the anode material used in the present invention is selected from one or more of the following materials, metals such as vanadium, chromium, copper and gold, or other alloys: metal oxides, such as: zinc oxide, indium tin oxide, indium zinc oxide and tin dioxide, combinations of metals and oxides, such as: zinc oxide: but is not limited thereto.
According to some embodiments of the present invention, the hole injection layer is formed of a material having an ability to transport holes, and thus, the material of the hole injection layer has a hole effect of injecting holes into the anode, has an excellent hole injection effect on the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and further, has an excellent thin film formation ability. The HOMO of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
According to some embodiments of the present invention, the hole transport layer is formed of a material capable of receiving holes from the anode or the hole injection layer, moving the holes to the light emitting layer, and having high mobility to the holes.
According to some embodiments of the present invention, the hole injection material and the hole transport material include at least one of aromatic amine derivatives (e.g., NPB, SqMA1), hexaazatriphenylene derivatives (e.g., HACTN), indolocarbazole derivatives, conductive polymers (e.g., PEDOT/PSS), phthalocyanine or porphyrin derivatives, dibenzoindenofluorenamine, spirobifluorenamine, but are not limited thereto.
According to some embodiments of the present invention, the hole injection layer and the hole transport layer may be formed, for example, using an aromatic amine derivative of the general formula:
Figure BDA0002290195040000121
the groups R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine.
According to some embodiments of the present invention, the material for forming the electron blocking layer is not particularly limited, and in general, compounds capable of satisfying the following conditions 1 or/and 2 can be considered:
1, the method comprises the following steps: a shallower LUMO level (smaller absolute value) is provided in order to reduce the number of electrons leaving the light-emitting layer and thereby increase the probability of recombination of electrons and holes in the light-emitting layer.
And 2, a step of: the light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
According to some embodiments of the present invention, the material forming the electron blocking layer includes, but is not limited to, aromatic amine derivatives (e.g., NPB), spirobifluorene amines (e.g., SpMA2), wherein the structures of a portion of the electron blocking material and the hole injecting material and the hole transporting material are similar.
According to some embodiments of the present invention, the light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and preferably a material having good quantum efficiency for fluorescence or phosphorescence.
According to some embodiments of the present invention, the light emitting layer may include a host material and a guest material.
According to some embodiments of the present invention, the host material may include anthracene derivatives, carbazole derivatives, fluorene derivatives, arylamine derivatives, organosilicon derivatives, carbazole-triazine derivatives, and phosphoxy derivatives, but is not limited thereto.
In some preferred embodiments of the invention, the anthracene derivative has the general formula:
Figure BDA0002290195040000131
the phosphorus oxy derivative has the following general formula:
Figure BDA0002290195040000141
in the general formulae of the above anthracene derivatives and phosphonoxy derivatives, R11、R12、R13、R14、R15And R16Each independently selected from the group represented by a single bond, hydrogen, deuterium, an alkyl group, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and a substituent thereof.
According to some embodiments of the invention, the guest material is preferably a compound that produces emission via at least one of phosphorescence, fluorescence, TADF (thermally activated delayed fluorescence), MLCT (metal to ligand charge transfer), HLCT (with hybrid CT states), and triplet-triplet annihilation methods.
According to some embodiments of the present invention, the guest material in the light emitting layer may include perylene derivatives, anthracene derivatives, fluorene derivatives, distyrylaryl derivatives, arylamine derivatives, organosilicon derivatives, organoboron derivatives, carbazole-triazine derivatives, acridine derivatives, ketone-containing derivatives, sulfone-based derivatives, cyano derivatives, and xanthene derivatives, but is not limited thereto.
In some preferred embodiments of the present invention, the sulfone-based derivative has the following general formula:
Figure BDA0002290195040000142
the ketone derivatives have the general formula shown below:
Figure BDA0002290195040000143
in the above general formulae of the sulfone-based derivatives and ketone-based derivatives, R20、R21、R22And R23Each independently selected from the group represented by a single bond, hydrogen, deuterium, an alkyl group, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, triphenylene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and a substituent thereof.
According to some embodiments of the present invention, the material of the hole blocking layer may also preferably be a compound having the following condition 1 and/or 2:
1, the method comprises the following steps: the light-emitting layer has a deep HOMO level (large absolute value), and the purpose of the light-emitting layer is to reduce the number of holes leaving the light-emitting layer, thereby improving the recombination probability of electrons and holes in the light-emitting layer.
And 2, a step of: the light emitting layer has larger triplet energy, and the purpose of the light emitting layer is to reduce the number of excitons which leave the light emitting layer, thereby improving the efficiency of exciton conversion and light emission.
According to some embodiments of the present invention, the material forming the hole blocking layer may include, for example, a phenanthroline-containing derivative (e.g., Bphen, BCP), a triphenylene derivative, a benzimidazole derivative, but is not limited thereto.
According to some embodiments of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a cathode, has an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injection layer, and has an excellent thin film forming ability. Electron injection layer materials include, for example, LiF, CsF, CsCO3LiQ, but not limited thereto.
According to some embodiments of the present invention, a material having a small work function, which allows electrons to be smoothly injected into the organic material layer, is generally preferable to form the cathode material, and the cathode material that can be used in the present disclosure may be selected from one or more of the following materials, one or more of Al, Mg, and Ag.
The present invention will be described in detail below by way of examples. In the following examples, various raw materials used are all common commercial products unless otherwise specified.
Preparation example 1: synthesis of Compound 1
Figure BDA0002290195040000161
Synthesis of intermediate 1-1: dissolving 0.1mol of 2-bromo-1, 10-phenanthroline in 260ml of 1, 4-dioxygenIntroducing nitrogen into a hexacyclic solvent, stirring, and then adding 0.1mol of pinacol diboride, 0.25mol of potassium acetate and 0.001mol of PdCl2(dppf) ([1,1' -bis (diphenylphosphino) ferrocene)]Palladium dichloride), heating to reflux, detecting the basic reaction of the raw materials by HPLC after 4 hours, decompressing and spin-drying the reaction liquid, and performing column chromatography on the residue to obtain a white intermediate 1-1 (yield: 83%).
Synthesis of intermediates 1-2: 0.083mol of intermediate 1-1 is dissolved in 260ml of 1, 4-dioxane solvent, nitrogen is introduced and stirred, then 0.083mol of 4-bromo-1-iodo dibenzofuran, 0.21mol of potassium carbonate and 0.83mmol of tetrakis (triphenylphosphine) palladium are added, the temperature is raised to reflux, after 5h, HPLC (high performance liquid chromatography) detects that the raw materials are basically completely reacted, the reaction solution is decompressed and dried, and the residue is subjected to column chromatography to obtain light yellow intermediate 1-2 (yield: 72%).
Synthesis of intermediates 1 to 3: the synthesis method was the same as that of the intermediate 1-1, to obtain a pale yellow intermediate 1-3 (yield: 80%).
Synthesis of Compound 1: the synthesis method was the same as that of the intermediate 1-2, to obtain the pale yellow compound 1 (yield: 72%).
Mass spectrum: C39H23N5O, theoretical value: 577.19, found: 577.1.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.25～7.43(3H，m)，7.43～7.61(9H，m)，7.79～7.91(2H，m)，7.95～8.01(1H，m)，8.12～8.18(1H，m)，8.31～8.48(6H，m)，8.82～8.77(1H，m)。
preparation example 2: synthesis of Compound 3
Figure BDA0002290195040000171
Synthesis of Compound 3: the synthesis method was the same as that of the intermediate 1-2, to obtain the pale yellow compound 3 (yield: 73%).
Mass spectrum: C45H27N5O, theoretical: 653.22, found: 653.2.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.21～7.43(5H，m)，7.44～7.61(9H，m)，7.79～7.91(2H，m)，7.92～8.01(3H，m)，8.11～8.18(1H，m)，8.30～8.48(6H，m)，8.76～8.83(1H，m)。
preparation example 3: synthesis of Compound 6
Figure BDA0002290195040000172
Synthesis of intermediate 6-1: the synthesis method was the same as that of intermediate 1-2, giving pale yellow intermediate 6-1 (yield: 72%).
Synthesis of intermediate 6-2: the synthesis method was the same as that of the intermediate 1-1, to obtain a pale yellow intermediate 6-2 (yield: 78%).
Synthesis of Compound 6: the synthesis method was the same as that of intermediate 1-2, and light yellow compound 6 was obtained (yield: 69%).
Mass spectrum: C45H27N5O, theoretical: 653.22, found: 653.3.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.22～7.43(5H，m)，7.47～7.61(9H，m)，7.73～7.90(3H，m)，7.95～8.01(1H，m)，8.32～8.48(6H，m)，8.65～8.72(2H，m)，8.79～8.82(1H，m)。
preparation example 4: synthesis of Compound 15
Figure BDA0002290195040000181
Synthesis of intermediate 15-1: the synthesis method was the same as that of intermediate 1-2, yielding pale yellow intermediate 15-1 (yield: 75%).
Synthesis of intermediate 15-2: the synthesis method was the same as that of intermediate 1-1, yielding pale yellow intermediate 15-2 (yield: 80%).
Synthesis of compound 15: the synthesis method was the same as that of the intermediate 1-2, to obtain the pale yellow compound 15 (yield: 72%).
Mass spectrum: C46H28N4O, theoretical value: 652.23, found: 652.2.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.20～7.28(2H，m)，7.29～7.43(3H，m)，7.44～7.62(9H，m)，7.72～7.79(1H，m)，7.84～8.02(8H，m)，8.18～8.25(2H，m)，8.35～8.49(2H，m)，8.76～8.84(1H，m)。
preparation example 5: synthesis of Compound 19
Figure BDA0002290195040000191
Synthesis of compound 19: the synthesis method was the same as that of intermediate 1-2, and light yellow compound 19 was obtained (yield: 73%).
Mass spectrum: C46H28N4O, theoretical value: 652.23, found: 652.2.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.21～7.61(14H，m)，7.78～8.01(5H，m)，8.12～8.18(1H，m),8.20～8.25(1H，m),8.27～8.48(6H，m),8.77～8.83(1H，m)。
preparation example 6: synthesis of Compound 27
Figure BDA0002290195040000192
Synthesis of intermediate 27-1: the synthesis method was the same as that of intermediate 1-2, giving pale yellow intermediate 27-1 (yield: 70%).
Synthesis of intermediate 27-2: the synthesis method was the same as that of intermediate 1-1, giving pale yellow intermediate 27-2 (yield: 74%).
Synthesis of compound 27: the synthesis method was the same as that of intermediate 1-2, and light yellow compound 27 was obtained (yield: 70%).
Mass spectrum: C45H27N5S, theoretical: 669.20, found: 669.1.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.21～7.27(2H，m)，7.28～7.36(2H，m)，7.47～7.52(6H，m)，7.54～7.61(3H，m)，7.82～7.90(3H，m),7.93～7.99(2H，m),8.22～8.27(1H，m),8.33～8.41(5H，m),8.43～8.48(2H，m),8.77～8.82(1H，m)。
preparation example 7: synthesis of Compound 35
Figure BDA0002290195040000201
Synthesis of compound 35: the synthesis method was the same as that of intermediate 1-2, and light yellow compound 35 was obtained (yield: 73%).
Mass spectrum: C46H28N4S, theoretical value: 668.20, found: 668.1.
1H-NMR(400MHz，CDCl3)(ppm)δ＝7.21～7.37(4H，m)，7.42～7.62(9H，m)，7.80～8.02(9H，m)，8.21～8.29(2H，m)，8.36～8.49(3H，m),8.77～8.83(1H，m)。
the structures of the organic electroluminescent devices referred to in the following device examples 1 to 13 and device comparative examples 1 to 4 were:
ITO/HAT-CN(5nm)/NPB(60nm)/TAPC(10nm)/DIC-TRZ:Ir(ppy)3(weight ratio 92:8, 30nm)/DMIC-TRZ (5nm)/ETL (30nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
Figure BDA0002290195040000211
device example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-4Pa, carrying out vacuum evaporation on the anode layer film to form HATCN as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 5 nm; then evaporating a hole transport layer NPB with the evaporation rate of 0.1nm/s and the thickness of 60 nm; TAPC is evaporated on the hole transport layer in vacuum to serve as an electron blocking layer, the evaporation rate is 0.1nm/s, and the thickness is 10 nm;
in the hole to transmitThe light-emitting layer of the vacuum evaporation device on the light-transmitting layer comprises a host material and a guest material, and the evaporation rate of the host material DIC-TRZ is adjusted to be 0.1nm/s and the evaporation rate of the guest material Ir (ppy) by using a multi-source co-evaporation method3The evaporation rate is set to be 8% of the evaporation rate of the main material, and the total film thickness of the evaporation is 30 nm;
vacuum evaporating a hole blocking layer DMIC-TRZ of the device on the light-emitting layer, wherein the evaporation rate is 0.1nm/s, and the thickness is 5 nm; then evaporating an electron transport layer, and adjusting the evaporation rates of ET-1 and the compound 1 to be 0.1nm/s and the total film thickness of evaporation to be 30nm by using a multi-source co-evaporation method;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Device example 2 to device example 13
Organic electroluminescent devices of device examples 2 to 13 were produced in a similar manner to device example 1, except that compound 1 in device example 1 was replaced with compounds 3, 6, 7, 10, 15, 19, 27, 31, 35, 39, 47, 29, respectively.
Comparative device example 1 to comparative device example 4
Organic electroluminescent devices of device comparative examples 1 to 4 were prepared in a similar manner to device example 1, except that compound 1 in device example 1 was replaced with D-ET-1, D-ET-2, D-ET-3, D-ET-4, respectively.
Figure BDA0002290195040000221
Test example 1
At a luminance of 10000cd/m2Next, the driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1 to 13 and device comparative examples 1 to 4 were measured, and the results are shown in table 1.
TABLE 1
Figure BDA0002290195040000222
Figure BDA0002290195040000231
From the experimental results shown in table 1, it can be seen that the compound of the present invention has a lower driving voltage and a higher luminous efficiency as an electron transport material of an organic electroluminescent device, compared to the prior art.
The structures of the organic electroluminescent devices referred to in the following device examples 14 to 19 and device comparative examples 5 to 7 were:
ITO/HATCN (5nm)/NPB (60nm)/TCTA (10nm)/BH: BD (weight ratio 95:5, 30nm)/HBL (5nm)/TPBI: ET-1 (weight ratio 1:1, 30nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
Figure BDA0002290195040000232
Figure BDA0002290195040000241
device example 14
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-4Pa, carrying out vacuum evaporation on the anode layer film to form HATCN as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 5 nm; then evaporating a hole transport layer NPB with the evaporation rate of 0.1nm/s and the thickness of 60 nm; TCTA is vacuum evaporated on the hole transport layer as an electron blocking layer at an evaporation rate of 0.1nm/s and a thickness of 10 nm;
a light-emitting layer of the device is vacuum evaporated on the hole transport layer, the light-emitting layer comprises a host material and a guest material, the evaporation rate of the host material BH is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, the evaporation rate of the guest material BD is set to be 5% of the evaporation rate of the host material, and the total evaporation film thickness is 30 nm;
vacuum evaporating a hole blocking layer compound 5 of the device on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the thickness is 5 nm; then evaporating an electron transport layer, and adjusting the evaporation rates of ET-1 and TPBI to be 0.1nm/s and the total film thickness of evaporation to be 30nm by using a multi-source co-evaporation method;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
Device example 15 to device example 19
Organic light-emitting devices of device example 15 to device example 19 were produced in a similar manner to device example 14, except that compound 5 in device example 15 was replaced with compounds 6, 15, 46, 52, 62.
Comparative device example 5 to comparative device example 7
Organic electroluminescent devices of comparative device examples 5 to 7 were prepared in a similar manner to device example 14, except that compound 5 in device example 14 was replaced with D-ET-2, D-ET-4, BCP.
Test example 2
At a luminance of 1000cd/m2Next, the driving voltage and current efficiency of the organic electroluminescent devices prepared in device example 14 to device example 19 and device comparative example 1 to device comparative example 3 were measured, and the results are shown in table 2.
TABLE 2
Examples Hole blocking layer Drive voltage (V) Efficiency (cd/A)
Device example 14 Compound 5 4.61 6.83
Device example 15 Compound 6 4.56 6.77
Device example 16 Compound 15 4.37 6.41
Device example 17 Compound 46 4.42 6.46
Device example 18 Compound 52 4.68 6.65
Device example 19 Compound 62 4.45 6.52
Comparative device example 5 D-ET-2 4.83 5.75
Comparative device example 6 D-ET-4 4.96 5.82
Comparative device example 7 BCP 5.12 5.63
As can be seen from the experimental results shown in table 2, when the compound of the present invention is used as a hole blocking layer material of an organic electroluminescent device, the organic electroluminescent device of the present invention has a low driving voltage and a high luminous efficiency, compared to the prior art.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.

Claims (4)

1. A phenanthroline structure-containing compound, which is selected from at least one of the following compounds:
Figure FDA0003138050630000011
2. use of the compound of claim 1 in an organic electroluminescent device.
3. An organic electroluminescent element comprising one or more compounds selected from the compounds according to claim 1, wherein the compounds are present in at least one of an electron transport layer, a light-emitting layer and a hole-blocking layer of the organic electroluminescent element.
4. The organic electroluminescent device according to claim 3, wherein the compound is present in an electron transport layer and/or a hole blocking layer of the organic electroluminescent device.
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