CN111116561B - Compound containing condensed ring structure, application thereof and organic electroluminescent device - Google Patents

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

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CN111116561B
CN111116561B CN201911328990.0A CN201911328990A CN111116561B CN 111116561 B CN111116561 B CN 111116561B CN 201911328990 A CN201911328990 A CN 201911328990A CN 111116561 B CN111116561 B CN 111116561B
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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 condensed ring structure, application thereof and an organic electroluminescent device, wherein the compound has a structure shown in a formula (I). The compound provided by the invention has proper HOMO energy level and LUMO energy level, and can realize the adjustment of the HOMO energy level and the LUMO energy level in a small range, so that the energy levels of the HOMO energy level and the LUMO energy level of adjacent material layers are high in matching degree, thereby reducing hole and electron injection barriers, and when the compound is applied to an organic electroluminescent device, the driving voltage can be reduced.

Description

Compound containing condensed ring 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 condensed ring 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.
At present, the light emitting layer of the high-efficiency OLED mainly adopts an organic phosphorescent material, because the radiative transition of triplet excitons of most organic molecules is forbidden and is not beneficial to the light emission of the device, but the spin-orbit coupling effect of noble metal atoms enables the radiative transition from an excited state triplet state to a ground state which is originally spin-forbidden to be locally allowed, the singlet excitons and the triplet excitons are effectively utilized, the internal quantum efficiency can reach 100% theoretically, the intersystem crossing probability from the singlet excited state to the triplet excited state is improved, the high-efficiency phosphorescent light emission is generated, but the triplet excitons have long service life, high-concentration quenching is easily caused, the host-guest doping is adopted, the concentration quenching can be effectively avoided, and further, the high-performance host material and guest material need to be developed, and the red light is used as one of three primary colors to display the OLED and is very important. Therefore, the development of high-performance red hosts is of great importance.
Disclosure of Invention
The invention aims to overcome the defects of high driving voltage, low luminous efficiency and low brightness of the organic electroluminescent device in the prior art.
In order to achieve the above object, a first aspect of the present invention provides a compound having a condensed ring structure, the compound having a structure represented by formula (I),
Figure BDA0002329099120000021
wherein, in the formula (I),
l is absent or is a linking group provided by benzene or a structure represented by formula (II) wherein X is O or S;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothienyl group, a group represented by the formula (III), and a group represented by the formula (IV).
A second aspect of the invention provides the use of the aforementioned compounds in an organic electroluminescent device.
A third aspect of the present invention provides an organic electroluminescent device containing one or two or more compounds among the aforementioned compounds, the compounds being present in at least one of an electron transport layer, a light-emitting layer, and a hole blocking layer of the organic electroluminescent device.
In particular, the compounds of the invention also have the following advantages:
1. the compound can balance electrons and holes in a device, so that a wider carrier recombination region is obtained, and the luminous efficiency and the brightness are improved;
2. the condensed ring compound provided by the invention can well adjust the energy level ranges of HOMO and LUMO, so that the energy level matching degree of the condensed ring compound and the adjacent material layer is high, and the injection barrier of holes and electrons can be reduced, thereby reducing the driving voltage and improving the luminous efficiency.
3. The compound provided by the invention has high triplet state energy level, can limit the backflow of triplet state energy from a phosphorescent object to a host, can limit triplet state excitons in a light-emitting layer, and further can improve the light-emitting efficiency and the brightness.
4. The compound of the invention has small molecular weight and good stability, and is beneficial to vacuum evaporation film formation during device preparation.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and these ranges or values should be understood to encompass values close to these 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 compound having a condensed ring structure, which has a structure represented by the formula (I),
Figure BDA0002329099120000041
wherein, in the formula (I),
l is absent or is a linking group provided by benzene or a structure represented by formula (II) wherein X is O or S;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6Alkyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl, formulaAt least one of the group represented by the formula (III) and the group represented by the formula (IV).
Unless otherwise specified, the structural formula of the phenyl group according to the present invention is:
Figure BDA0002329099120000042
unless otherwise specified, the structural formula of the naphthyl group according to the present invention includes:
Figure BDA0002329099120000043
unless otherwise specified, the structural formula of the dibenzofuranyl group of the invention includes:
Figure BDA0002329099120000044
unless otherwise specified, the structural formula of the dibenzothienyl group of the present invention includes:
Figure BDA0002329099120000051
the structural formula of the group represented by the formula (III) according to the present invention includes, unless otherwise specified:
Figure BDA0002329099120000052
c in the present invention unless otherwise specified1-6The alkyl group of (a) includes: the linear, branched or cyclic alkyl group may be, for example, a linear, branched or cyclic alkyl group having a total number of carbon atoms of 1, 2, 3, 4, 5 or 6, and may be, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl groupMethylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, and the like.
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),
l is absent;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
Embodiment mode 2:
in the formula (I), the compound represented by the formula (I),
l is a linking group provided by benzene;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
Embodiment mode 3:
in the formula (I), the compound represented by the formula (I),
l is a phenyl group represented by the formula (V1),
Figure BDA0002329099120000061
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
Embodiment 4:
in the formula (I), the compound represented by the formula (I),
l is a linking group provided by the structure shown in formula (II) wherein X is O or S;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
Embodiment 5:
in the formula (I), the compound represented by the formula (I),
l is a group of formula (II1) or a group of formula (II2), in formula (II1) and formula (II2), X is each independently O or S;
Figure BDA0002329099120000071
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
Embodiment 6:
the compound having a structure represented by formula (I) is at least one compound selected from the compounds listed in claim 7.
Embodiment mode 7:
the compound having a structure represented by formula (I) is at least one compound selected from the compounds listed in claim 8.
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 invention will not be described in detail herein with respect to specific methods of preparing the various compounds of the invention, which should not be construed as limiting the invention to those skilled in the art.
As mentioned above, a second aspect of the present invention provides the use of the aforementioned compounds 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 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 at least one of the aforementioned compounds 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 containing one or two or more compounds among the aforementioned compounds, which are present in at least one layer of an electron transport layer, a light emitting layer and a hole blocking layer of the organic electroluminescent device.
Particularly preferably, the compound is present in the light-emitting layer of the organic electroluminescent device.
The compound of the present invention is further preferable as a red host material in a light-emitting layer of the organic electroluminescent device.
The inventors of the present invention found that when the compound of the present invention is used as a red host material in a light emitting layer of an organic electroluminescent device, the driving voltage of the organic electroluminescent device can be significantly reduced and the light emitting efficiency can be improved.
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 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 BDA0002329099120000101
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: the light-emitting layer has a shallow LUMO level (smaller absolute value) and the purpose thereof is to reduce the number of electrons leaving the light-emitting layer and to improve 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 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 BDA0002329099120000111
the ketone derivatives have the general formula shown below:
Figure BDA0002329099120000112
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): 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.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and as an electron transport material, a material that is capable of receiving electrons from the cathode, moving the electrons to the light emitting layer, and having high mobility to the electrons is suitable. Electron transport materials include, for example, Al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; hydroxyflavone-metal complexes, and the like, but are 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.
Unless otherwise specified, the room temperature described below indicates 25. + -. 1 ℃.
Preparation example 1: synthesis of Compound 3
Figure BDA0002329099120000121
Synthesis of intermediate 3-1: dissolving 50mmol of methyl 2- (4-bromophenyl) -2-oxoacetate in 120ml of toluene, adding 50mmol of phenylenediamine and 67ml of glacial acetic acid, stirring at room temperature for 1.5h, detecting the completion of the reaction of the raw materials, washing the reaction solution with water for 3 times, washing with 5 wt% NaOH aqueous solution for 2 times, washing with water for 2 times, and then carrying out anhydrous NaSO4Drying, adsorbing with 30g activated alumina, distilling under reduced pressure to obtain solid, placing into a round-bottom flask, adding 125ml 55 wt% aqueous HBr solution, absorbing tail gas with water, heating to 110 deg.C, reacting for 5h, cooling to room temperature, quenching with 125ml water, extracting with ethyl acetate for 6 times, extracting with sodium hydroxide aqueous solution for 3 times, adjusting pH to 5.5 with acetic acid, drying with anhydrous sodium sulfate, and recrystallizing to obtain white solid (yield: 50%).
Synthesis of intermediate 3-2: dissolving 10mmol of the intermediate 3-1 in 30ml of toluene solvent, adding 10mmol of A-1, 50mmol of sodium tert-butoxide, 0.1mmol of tris (dibenzylideneacetone) dipalladium and 0.1mmol of tri-tert-butylphosphine, stirring by introducing nitrogen, heating to reflux, detecting the completion of the reaction of the raw materials after 4h, decompressing and spin-drying the reaction liquid, and obtaining light yellow solid by column chromatography (yield: 72%).
Synthesis of intermediate 3-3: 7.2mmol of intermediate 3-2 was dissolved in 35ml of dichloromethane, trifluoromethanesulfonic anhydride was added dropwise, reaction was carried out at room temperature for 5 hours, the organic phase was taken out and spin-dried under reduced pressure, and the residue was subjected to column chromatography to give a pale yellow solid (yield: 90%).
Synthesis of Compound 3: 6mmol of the intermediate 3-3 is dissolved in 40ml of 1, 4-dioxane solvent, nitrogen is introduced and stirred, and 6mmol of 3-Biphenylboronic acid, 15mmol of K2CO30.06mmol of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, after 5h, detecting the basic reaction of the raw materials by HPLC, drying the reaction solution by spinning under reduced pressure, and performing column chromatography on the residue to obtain a yellow solid (yield: 72%).
Mass spectrum: C44H29N3, theoretical value: 599.24, found: 599.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.07-7.15 (2H, m), 7.33-7.50 (9H, m), 7.55-7.79 (10H, m), 7.89-7.97 (2H, m), 8.05-8.10 (2H, m), 8.24-8.29 (2H, m), 8.39-8.41 (1H, m), 8.45-8.49 (1H, m).
Preparation example 2: synthesis of Compound 6
Figure BDA0002329099120000141
Synthesis of Compound 6: synthesis method the same as that for Compound 3 gave a yellow solid (yield: 70%).
Mass spectrum: C44H27N3O, theoretical value: 613.22, found: 613.3. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.18 (2H, m), 7.30-7.43 (8H, m), 7.52-7.69 (5H, m), 7.76-7.84 (3H, m), 7.92-8.00 (3H, m), 8.08-8.15 (3H, m), 8.27-8.28 (1H, m), 8.30-8.32 (2H, m).
Preparation example 3: synthesis of Compound 7
Figure BDA0002329099120000142
Synthesis of compound 7: synthesis method the synthesis method of Compound 3 gave a yellow solid (yield: 75%).
Mass spectrum: C44H27N3O, theoretical value: 613.22, found: 613.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.09-7.18 (2H, m), 7.29-7.49 (9H, m), 7.51-7.71 (5H, m), 7.76-7.84 (2H, m), 7.92-8.00 (3H, m), 8.08-8.13 (2H, m), 8.16-8.20 (1H, m), 8.27-8.32 (3H, m).
Preparation example 4: synthesis of Compound 13
Figure BDA0002329099120000151
Synthesis of compound 13: synthetic method this method for compound 3 gave a yellow solid (yield: 72%).
Mass spectrum: C50H32N4, theoretical value: 688.26, found: 688.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.07-7.20 (4H, m), 7.33-7.44 (6H, m), 7.47-7.69 (11H, m), 7.76-7.84 (2H, m), 7.92-8.00 (2H, m), 8.04-8.12 (3H, m), 8.26-8.31 (2H, m), 8.41-8.44 (1H, m), 8.53-8.57 (1H, m).
Preparation example 5: synthesis of Compound 22
Figure BDA0002329099120000152
Synthesis of compound 22: synthesis method the same as that for Compound 3 gave a yellow solid (yield: 73%).
Mass spectrum: C50H31N3S, theoretical value: 705.22, found: 705.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.18 (2H, m), 7.27-7.44 (9H, m), 7.48-7.71 (6H, m), 7.76-7.88 (3H, m), 7.92-8.00 (2H, m), 8.07-8.13 (2H, m), 8.26-8.34 (3H, m), 8.42-8.47 (1H, m), 8.52-8.57 (1H, m), 8.83-8.88 (2H, m).
Preparation example 6: synthesis of Compound 25
Figure BDA0002329099120000161
Synthesis of intermediate 25-1: the same procedure as that for intermediate 3-1 was conducted to obtain a white solid (yield: 55%).
Synthesis of intermediate 25-2: the same procedure as that for the intermediate 3-3 was used to obtain a pale yellow solid (yield: 85%).
Synthesis of intermediate 25-3: under the protection of nitrogen, dissolving 50mmol of 1-bromo-4-iodo [ b, d ] dibenzofuran in 120ml of xylene solvent, sequentially adding 20mmol of A-1, 14.5mmol of cuprous chloride, 10mmol of hydrated 1, 10-phenanthroline and 150mmol of potassium hydroxide, heating and stirring, when the temperature is raised to 130 ℃, dropwise adding 30mmol of A-1 and 80ml of xylene mixed solution, keeping reflux reaction after dropwise adding, detecting that the reaction of raw materials is finished after 16h, dropwise adding 15ml of concentrated hydrochloric acid, stirring for 1h after dropwise adding, filtering, adding 1L of water into filtrate, standing and separating, washing an organic phase twice, adding anhydrous sodium sulfate, drying for 2h, leaching a filter cake with xylene, and concentrating the filtrate under pressure (about 0.09MPa and 85 ℃) until no more dripping, so as to obtain a brownish black substance. 0.5L of ethanol was added thereto with vigorous stirring, and a large amount of solid was precipitated, which was heated to reflux for 1 hour. After cooling to room temperature, stirring for 10h, filtering, rinsing the filter cake with 300ml of ethanol, and drying (0.08MPa, 80 ℃, 6h) to obtain a yellow solid (yield: 72%).
Synthesis of intermediate 25-4: dissolving 5mmol of intermediate 25-3 in 30ml of 1, 4-dioxane solvent, introducing nitrogen for protection and stirring, sequentially adding 5mmol of pinacol diboride, 12.5mmol of potassium acetate and 0.05mmol of [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride, heating and refluxing, detecting basic reaction of raw materials by HPLC after 4h, decompressing and spin-drying reaction liquid, and carrying out column chromatography on residues to obtain yellow solids (yield: 81%).
Synthesis of compound 25: dissolving 4mmol of intermediate 25-4 in 25ml of 1, 4-dioxane solvent, introducing nitrogen gas, stirring, sequentially adding 4mmol of 3-biphenylboronic acid and 10mmol of K2CO30.04mmol of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, after 5h, detecting the basic reaction of the raw materials by HPLC, drying the reaction solution by spinning under reduced pressure, and performing column chromatography on the residue to obtain a yellow solid (yield: 71%).
Mass spectrum: C44H27N3O, theoretical value: 613.22, found: 613.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.20 (3H, m), 7.28-7.43 (8H, m), 7.52-7.71 (6H, m), 7.76-7.84 (2H, m), 7.93-8.05 (5H, m), 8.07-8.12 (3H, m).
Preparation example 7: synthesis of Compound 47
Figure BDA0002329099120000181
Synthesis of intermediate 47-1: the same procedure as that for the intermediate 3-2 was conducted to obtain a pale yellow solid (yield: 72%).
Synthesis of intermediate 47-2: the same procedure as that for the intermediate 3-3 was conducted to obtain a pale yellow solid (yield: 87%).
Synthesis of intermediate 47-3: the same procedure as that for intermediate 25-3 gave a pale yellow solid (yield: 70%).
Synthesis of intermediate 47-4: the same procedure as that for intermediate 25-4 gave a yellow solid (yield: 68%).
Synthesis of compound 47: synthesis method the same as for the compound 25 gave a yellow solid (yield: 73%).
Mass spectrum: C56H34N4S, theoretical value: 794.25, found: 794.3. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.06-7.24 (7H, m), 7.27-7.42 (6H, m), 7.49-7.70 (6H, m), 7.76-7.88 (3H, m), 7.92-7.98 (4H, m), 8.07-8.12 (2H, m), 8.16-8.21 (2H, m), 8.42-8.49 (3H, m), 8.52-8.57 (1H, m).
Preparation example 8: synthesis of Compound 48
Figure BDA0002329099120000191
Synthesis of Compound 48-1: dissolving 50mmol of intermediate 3-1 in 150ml of 1, 4-dioxane solvent, introducing nitrogen gas, stirring, sequentially adding 50mmol of dibenzothiophene-2-boric acid, 100mmol of K2CO3 and 0.5mmol of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 6h, performing reduced pressure spin-drying on reaction liquid, and performing column chromatography on residues to obtain a light yellow solid (yield: 71%).
Synthesis of intermediate 48-2: the same procedure as that for the intermediate 3-3 was conducted to obtain a pale yellow solid (yield: 88%).
Synthesis of compound 48: synthesis method As a result of synthesis of Compound 25, a yellow solid was obtained (yield: 73%).
Mass spectrum: C56H33N3S2, theoretical value: 811.21, found: 811.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.12-7.16 (2H, m), 7.23-7.25 (1H, m), 7.29-7.33 (2H, m), 7.36-7.41 (4H, m), 7.54-7.62 (4H, m), 7.65-7.69 (2H, m), 7.78-7.82 (2H, m), 7.85-7.90 (4H, m), 7.94-8.00 (3H, m), 8.09-8.13 (3H, m), 8.18-8.20 (1H, d), 8.44-8.46 (2H, d), 8.50-8.51 (1H, m), 8.85-8.87 (2H, d).
Preparation example 9: synthesis of Compound 69
Figure BDA0002329099120000201
Synthesis of intermediate 69-1: the same procedure as that for intermediate 48-1 was used to obtain a white solid (yield: 78%).
Synthesis of intermediate 69-2: the synthesis was performed in the same manner as for intermediate 3-3 to obtain a white solid (yield: 89%).
Synthesis of intermediate 69-3: the same procedure as that for intermediate 25-3 gave a yellow solid (yield: 74%).
Synthesis of intermediate 69-4: the same procedure as that for intermediate 25-4 gave a yellow solid (yield: 67%).
Synthesis of compound 69: synthesis method As a result of synthesis of Compound 25, a yellow solid was obtained (yield: 70%).
Mass spectrum: C56H33N3OS, theoretical value: 795.23, found: 795.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.17 (2H, m), 7.27-7.28 (1H, m), 7.30-7.34 (2H, m), 7.35-7.43 (6H, m), 7.51-7.71 (7H, m), 7.77-7.88 (3H, m), 7.94-8.04 (5H, m), 8.06-8.12 (3H, m), 8.43-8.47 (1H, m), 8.68-8.70 (1H, d), 8.84-8.85 (1H, m), 8.87-8.88 (1H, m).
Preparation example 10: synthesis of Compound 133
Figure BDA0002329099120000211
Synthesis of intermediate 133-1: the same procedure as that for intermediate 25-3 gave a yellow solid (yield: 76%).
Synthesis of intermediate 133-2: the same procedure as that for intermediate 25-4 gave a yellow solid (yield: 73%).
Synthesis of compound 133: synthetic method the same as the synthetic method of compound 25 gave a yellow solid (yield: 70%).
Mass spectrum: C44H27N3O, theoretical value: 613.22, found: 613.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.18 (2H, m), 7.28-7.48 (8H, m), 7.57-7.81 (8H, m), 7.94-7.98 (2H, m), 7.99-8.06 (2H, m), 8.08-8.09 (1H, m), 8.10-8.2 (1H, d), 8.17-8.23 (2H, m), 8.57-8.58 (1H, d).
Preparation example 11: synthesis of Compound 134
Figure BDA0002329099120000221
Synthesis of intermediate 134-1: the same procedure as that for intermediate 3-1 was used to obtain a white solid (yield: 52%).
Synthesis of intermediate 134-2: the same procedure as that for the intermediate 3-3 was conducted to obtain a pale yellow solid (yield: 87%).
Synthesis of compound 134: synthetic method the same as the synthetic method of compound 25 gave a yellow solid (yield: 67%).
Mass spectrum: C50H31N3O, theoretical value: 689.25, found: 689.3. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.18 (2H, m), 7.36-7.51 (8H, m), 7.57-7.82 (10H, m), 7.87-7.98 (4H, m), 8.08-8.12 (2H, m), 8.17-8.23 (2H, m), 8.68-8.70 (1H, d), 8.84-8.85 (1H, m), 8.87-8.89 (1H, m).
Preparation example 12: synthesis of Compound 209
Figure BDA0002329099120000231
Synthesis of intermediate 209-1: the same procedure as that for the intermediate 3-1 was conducted to obtain a pale yellow solid (yield: 48%).
Synthesis of intermediate 209-2: the same procedure as that for the intermediate 3-3 was conducted to obtain a pale yellow solid (yield: 86%).
Synthesis of intermediate 209-3: the same procedure as that for intermediate 25-3 gave a yellow solid (yield: 65%).
Synthesis of intermediate 209-4: the same procedure as that for intermediate 25-4 gave a yellow solid (yield: 73%).
Synthesis of compound 209: synthetic method the same as that for compound 25 gave a pale yellow solid (yield: 72%).
Mass spectrum: C48H29N3O, theoretical value: 663.23, found: 663.2. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.06-7.16 (3H, m), 7.32-7.44 (6H, m), 7.51-7.64 (6H, m), 7.72-7.78 (2H, m), 7.98-8.07 (7H, m), 8.11-8.18 (2H, m), 8.23-8.28 (1H, m), 8.47-8.51 (1H, m), 8.96-8.98 (1H, m).
Preparation example 13: synthesis of Compound 218
Figure BDA0002329099120000241
Synthesis of intermediate 218-1: the same procedure as that for the intermediate 3-1 was conducted to obtain a white solid (yield: 52%).
Synthesis of intermediate 218-2: the same procedure as that for intermediate 48-1 was conducted to obtain a pale yellow solid (yield: 68%).
Synthesis of intermediate 218-3: the same procedure as that for the intermediate 3-3 was conducted to obtain a pale yellow solid (yield: 84%).
Synthesis of compound 218: the same procedure as that for intermediate 3-2 was followed to give a yellow solid (yield: 69%).
Mass spectrum: C44H29N3, theoretical value: 599.24, found: 599.1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.18 (2H, m), 7.37-7.52 (10H, m), 7.57-7.62 (2H, m), 7.64-7.69 (2H, m), 7.73-7.82 (6H, m), 7.94-7.98 (2H, m), 8.08-8.12 (2H, m), 8.32-8.33 (1H, m), 8.38-8.39 (2H, d).
Preparation example 14: synthesis of Compound 229
Figure BDA0002329099120000251
Synthesis of intermediate 229-1: the same procedure as that for intermediate 48-1 gave a pale yellow solid (yield: 72%).
Synthesis of intermediate 229-2: the same procedure as that for the intermediate 3-3 was followed to give a pale yellow solid (yield: 89%).
Synthesis of compound 229: the same procedure as that for intermediate 3-2 was followed to give a yellow solid (yield: 72%).
Mass spectrum: C44H27N3O, theoretical value: 613.22, found: 613.3. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.10-7.18 (2H, m), 7.27-7.31 (2H, m), 7.33-7.44 (7H, m), 7.52-7.63 (3H, m), 7.64-7.70 (2H, m), 7.78-7.82 (2H, m), 7.94-8.04 (4H, m), 8.06-8.12 (3H, m), 8.84-8.85 (1H, m), 8.87-8.88 (1H, m).
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, evaporating HAT-CN as a hole injection layer on the anode layer film in vacuum, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation 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 evaporated on the hole transport layer in vacuum to be used as an electron blocking layer, and the evaporation rate is 0.1nm/s and 10nm in thickness;
the luminescent layer of the device is vacuum evaporated on the hole transport layer and comprises a host material and a guest material, and the evaporation rate of a host material compound 3 is adjusted to be 0.1nm/s and the guest material (piq) is adjusted by using a multi-source co-evaporation method2Ir (acac) evaporation rate is set to be 10% of the evaporation rate of the main material, and the total evaporation film thickness is 30 nm;
vacuum evaporating a hole blocking layer TPBi 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 electronic transmission layer, and adjusting the evaporation rates of ET-1 and ET-2 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 examples 2 to 22
Organic light-emitting devices of device examples 2 to 22 were produced in a similar manner to device example 1, except that compound 3 in device example 1 was replaced with the corresponding compound in table 1.
Comparative device examples 1 to 3
The organic electroluminescent devices of comparative device examples 1 to 3 were prepared in a similar manner to device example 1, except that compound 3 in device example 1 was replaced with RH-1, RH-2, RH-3, respectively.
Figure BDA0002329099120000261
Figure BDA0002329099120000271
The structures of the organic electroluminescent devices of the above device examples 1 to 22 and device comparative examples 1 to 3 were summarized as follows:
ITO/HAT-CN (5nm)/NPB (60nm)/TCTA (10nm)/EML (30nm)/TPBi (5nm)/ET-1: ET-2 (weight ratio 1:1, 30nm)/LiF (1 nm)/Al.
The molecular structure involved is as follows:
Figure BDA0002329099120000272
test example 1
At a luminance of 2000cd/m2Next, the driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1 to 22 and device comparative examples 1 to 3 were measured, and the results are shown in table 1.
TABLE 1
Figure BDA0002329099120000273
Figure BDA0002329099120000281
As can be seen from the experimental results shown in table 1, when the compound of the present invention is used as a red host material of an organic electroluminescent device, the compound has a lower driving voltage and a higher luminous efficiency than those of 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 (11)

1. A compound having a condensed ring structure, which has a structure represented by the formula (I),
Figure FDA0003628238910000011
wherein, in the formula (I),
l is absent or is a linking group provided by benzene or a structure represented by formula (II) wherein X is O or S;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
2. The compound according to claim 1, wherein, in formula (I),
l is absent;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
3. The compound according to claim 1, wherein, in formula (I),
l is a linking group provided by benzene;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
4. The compound according to claim 3, wherein, in formula (I),
l is a phenyl group represented by the formula (V1),
Figure FDA0003628238910000021
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothienyl group, a group represented by the formula (III), and a group represented by the formula (IV).
5. The compound according to claim 1, wherein, in formula (I),
l is a linking group provided by the structure shown in formula (II) wherein X is O or S;
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
6. The compound according to claim 5, wherein, in formula (I),
l is a group of formula (II1) or a group of formula (II2), in formula (II1) and formula (II2), X is each independently O or S;
Figure FDA0003628238910000031
a is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl;
the substituent optionally contained in A is selected from C1-6At least one of an alkyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a group represented by the formula (III), and a group represented by the formula (IV).
7. The compound of claim 1, wherein the compound of formula (I) is selected from at least one of the following compounds:
Figure FDA0003628238910000032
Figure FDA0003628238910000041
Figure FDA0003628238910000051
Figure FDA0003628238910000061
Figure FDA0003628238910000071
Figure FDA0003628238910000081
Figure FDA0003628238910000091
Figure FDA0003628238910000101
Figure FDA0003628238910000111
Figure FDA0003628238910000121
8. the compound of claim 1, wherein the compound of formula (I) is selected from at least one of the following compounds:
Figure FDA0003628238910000122
Figure FDA0003628238910000131
9. use of a compound according to any one of claims 1 to 8 in an organic electroluminescent device.
10. An organic electroluminescent device comprising one or more compounds of the compounds according to any one of claims 1 to 8, 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 device.
11. The organic electroluminescent device according to claim 10, wherein the compound is present in a light emitting layer of the organic electroluminescent device.
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