CN112358455B - Dibenzo seven-membered heterocyclic compound and preparation method and application thereof - Google Patents

Dibenzo seven-membered heterocyclic compound and preparation method and application thereof Download PDF

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CN112358455B
CN112358455B CN202011279369.2A CN202011279369A CN112358455B CN 112358455 B CN112358455 B CN 112358455B CN 202011279369 A CN202011279369 A CN 202011279369A CN 112358455 B CN112358455 B CN 112358455B
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dibenzo
heterocyclic compound
membered heterocyclic
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汪康
王进政
黄悦
赵贺
李贺
崔建勇
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses a dibenzo-seven-membered heterocyclic compound and a preparation method and application thereof, belonging to the field of preparation and application of luminescent materials. The dibenzo-seven-membered heterocyclic compound disclosed by the invention has the following structure:

Description

Dibenzo seven-membered heterocyclic compound and preparation method and application thereof
Technical Field
The invention belongs to the field of preparation and application of luminescent materials, relates to a dibenzo-seven-membered heterocyclic compound, and particularly relates to a dibenzo-seven-membered heterocyclic compound, a preparation method thereof and an organic electroluminescent device containing the dibenzo-seven-membered heterocyclic compound.
Background
In order to improve the luminance, efficiency and lifetime of organic electroluminescent devices, a multilayer structure is generally used in the devices. These multilayer structures include a light-emitting layer and various auxiliary organic layers such as a hole injection layer, a hole transport layer, an electron transport layer, and the like. The auxiliary organic layers have the functions of improving the injection efficiency of carriers (holes and electrons) between interfaces of each layer and balancing the transmission of the carriers between the layers, so that the brightness and the efficiency of the device are improved. The hole transport layer is used for enhancing the hole transport capability of the device and blocking electrons in the light-emitting layer, so that the recombination probability of the electrons and the holes is improved.
A substance having a high hole mobility is developed for the reference hole transport layer in order to reduce the driving voltage, and a substance having a HOMO valence close to that of the light emitting layer is developed for the purpose of increasing the hole mobility. And since the hole mobility is faster than the electron mobility, an electron imbalance occurs, so that the light emitting efficiency and the lifetime are finally reduced.
Because the current synthesis process of organic electroluminescent compounds is complex, takes long time and has a short lifetime, and it is necessary to select a more suitable electroluminescent material with high performance to achieve the comprehensive characteristics of high efficiency, long lifetime and low voltage of the device in view of the current industrial application requirements of the OLED device and the photoelectric characteristic requirements of the OLED device, further development of organic electroluminescent compounds is imminent.
Disclosure of Invention
In view of the above, the present invention provides a dibenzo-seven-membered heterocyclic compound, which has good thermal stability and simple preparation route, and an organic electroluminescent device containing the compound has excellent luminous efficiency and long lifetime, and is an organic electroluminescent compound with excellent properties, and is suitable for popularization and application.
The invention provides a dibenzo-seven-membered heterocyclic compound, which has the following structural general formula:
Figure GDA0003660117880000021
wherein X represents a bond and X represents-O-, -S-, -SO2-、-C(R3)(R4)-、-N(R5)-、-Si(R6)(R7)-、-Sn(R8)(R9) -or-Ge (R)10)(R11) (ii) a Wherein R is3～R11Each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-membered to 30-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl;
l is a connecting bond, and L is a substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (3-to 15-membered) heteroarylene;
Ar1and Ar2Are the same substituent or different substituents; and Ar1And Ar2At least one selected from the following groups: substituted or unsubstituted (C1-C30) cycloalkyl, substituted or unsubstituted (3-to 30-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C6-C30) arylamino, substituted or unsubstituted (3-to 30-membered) heteroarylamino;
R1and R2Are the same substituent or different substituents; and R is1And R2At least one selected from the following groups: hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid, phosphoric acid, boryl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-to 30-membered) heterocycloalkyl, substituted or unsubstituted (C6-to C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) arylamino, substituted or unsubstituted (C6-C30) aryloxy.
Preferably, X is-O-, -S-or-Si (R)6)(R7)-。
Preferably, Ar1And Ar2Each independently selected fromSubstituted or unsubstituted (C3-C15) cycloalkyl, substituted or unsubstituted (3-membered to 15-membered) heterocycloalkyl, substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (3-membered to 20-membered) heteroaryl.
Preferably, R1、R2Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C3-C20) cycloalkyl, substituted or unsubstituted (3-membered to 15-membered) heterocycloalkyl, substituted or unsubstituted (C6-C20) aryl, and substituted or unsubstituted (3-membered to 20-membered) heteroaryl.
Further preferably, said L, Ar1、Ar2And R1～R11The heteroatom in (3) is N, O or S.
It should be noted that, in the above technical solutions, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following:
deuterium, a halogen group, a nitrile group, a hydroxyl group, a carbonyl group, an ester group, a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted heterocyclylamino group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclyl group;
Or a substituent in which two or more substituents among the substituents shown above are linked, or no substituent. For example, "a substituent in which two or more substituents are linked" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
Illustratively, the dibenzo-seven-membered heterocyclic compound is selected from any one of the following structural formulas:
Figure GDA0003660117880000041
Figure GDA0003660117880000051
Figure GDA0003660117880000061
Figure GDA0003660117880000071
although specific structural formulas are listed above, the series of dibenzo-seven-membered heterocyclic compounds claimed in the present invention is not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of the groups and their substitution positions disclosed in the present invention, which are not described herein in detail and are all within the scope of the present invention.
The invention also provides a preparation method of the dibenzo-seven-membered heterocyclic compound, which comprises the following steps:
(1) under the protection of nitrogen, dissolving the raw material A and the raw material B in a toluene solution, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide, uniformly stirring, heating and refluxing to prepare an intermediate 1;
(2) under the protection of nitrogen, dissolving the raw material C in a DMF solution, then adding the intermediate 1 and potassium carbonate, and uniformly stirring to prepare a dibenzo-seven-membered heterocyclic compound shown in a chemical formula 1;
Specifically, the preparation reaction formula of the dibenzo seven-membered heterocyclic compound is as follows:
Figure GDA0003660117880000081
preferably, the mass addition ratio of the raw material A to the raw material B is 1: 1, adding the palladium catalyst, the phosphine ligand and sodium tert-butoxide in a mass ratio of 1: 5: 200.
preferably, the mass ratio of the raw material C, the intermediate 1 and the potassium carbonate added is 5: 5: 6.
more preferably, the preparation method of the dibenzo-seven-membered heterocyclic compound disclosed by the invention comprises the following specific steps:
step 1: under the protection of nitrogen, dissolving a raw material A (1.0eq) and a raw material B (1.0eq) in a toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.01eq), tri-tert-butylphosphine (0.05eq) and sodium tert-butoxide (2.0eq), uniformly stirring, heating to 90-110 ℃, and carrying out reflux reaction for 4.5-5 h; after the reaction is finished, slightly cooling to 75 ℃, filtering by using diatomite to remove salt and a catalyst, cooling the filtrate to room temperature, washing by using water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after the organic phases were combined, dried over anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator; completely dissolving the solid organic matter by using dichloromethane, slowly dripping the dissolved organic matter into petroleum ether solution, uniformly stirring, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying to prepare an intermediate 1;
And 2, step: under nitrogen protection, raw material C (1.0eq) was dissolved in DMF solution, followed by addition of intermediate 1(1.0eq) and potassium carbonate (K)2CO3) (1.2eq), heating the mixture to 90-110 ℃, and stirring for reacting for 19-20 h. After the reaction is finished, removing the solvent to obtain a solid organic matter; the remaining material was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V dichloromethane: V petroleum ether ═ 10:4) to obtain a dibenzo-heptatomic heterocyclic compound represented by chemical formula 1.
The dibenzo-heptatomic heterocyclic compound disclosed by the invention has the advantages of short synthetic route, simple process, easily obtained raw materials and low cost, and is suitable for industrial production and application.
The invention also claims the application of the dibenzo seven-membered heterocyclic compound in an organic electroluminescent device.
Specifically, the dibenzo seven-membered heterocyclic compound is used for preparing an organic electroluminescent device and comprises the following components: a first electrode, a second electrode, and one or more organic layers disposed between the first and second electrodes;
further, the organic layer refers to all layers between the first electrode and the second electrode of the organic electroluminescent device, and at least one of the organic layers is a light-emitting layer.
Exemplarily, when the organic layer comprises a hole transport layer, the hole transport layer contains the dibenzo-seven-membered heterocyclic compound of the present invention, that is, the dibenzo-seven-membered heterocyclic compound prepared according to the present disclosure can be applied to an organic electroluminescent device as a hole transport layer material.
Compared with the prior art, the invention discloses a dibenzo-seven-membered heterocyclic compound and a preparation method and application thereof, and the dibenzo-seven-membered heterocyclic compound has the following beneficial effects:
1) the present invention increases conformational isomers of molecules by decreasing the symmetry of the molecule, while R in chemical formula 11、R2The position is connected with a substituent group, so that the compound has a rigid planar structure, the molecular weight is increased, the molecules are not easy to crystallize and aggregate, and the material has higher photo-thermal stability.
2) The dibenzo-seven-element heterocyclic compound disclosed by the invention is used as a hole transport material for preparing an organic electroluminescent device, so that the luminous efficiency of the device is improved, the service life of the device is delayed, the driving voltage is reduced, and the dibenzo-seven-element heterocyclic compound is an organic electroluminescent compound with excellent performance and is suitable for popularization and application in the market.
Detailed Description
The technical solutions of the present invention will be described below clearly and completely in conjunction with the embodiments, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
The embodiment of the invention discloses a dibenzo-seven-membered heterocyclic compound, which can be used for preparing an organic electroluminescence period, can improve the luminous efficiency of a device, can prolong the service life of the device, and is suitable for popularization and application.
Example 1: synthesis of Compound-005
1. Under the protection of nitrogen, dissolving a raw material A-005(30.00mmol) and a raw material B-005(30.00mmol) in 200.00ml of toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.3mmol), tri-tert-butylphosphine (1.5mmol) and sodium tert-butoxide (60.00mmol), uniformly stirring, heating to 90 ℃, and carrying out reflux reaction for 5 hours; after the reaction is finished, slightly cooling to 75 ℃, filtering by using diatomite to remove salt and a catalyst, cooling the filtrate to room temperature, washing by using water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after combining the organic phases, drying was performed using anhydrous magnesium sulfate (30.00g), and the solvent was removed using a rotary evaporator; completely dissolving the solid organic matter by using dichloromethane, slowly dripping the dissolved organic matter into a petroleum ether solution, uniformly stirring, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying (80 ℃ for 4 hours) to prepare an intermediate 1(16.10g, yield: 87.61%);
Figure GDA0003660117880000101
2. Starting material C-005(26.14mmol) was dissolved in 180.00ml DMF under nitrogen blanket, followed by the addition of intermediate 1(26.14mmol) and potassium carbonate (K)2CO3) (31.37mmol), the mixture was warmed to 100 ℃ and the reaction stirred for 20 h; after the reaction is finished, removing the solvent to obtain a solid organic matter; using methylene chloride and petroleum ether (V)Methylene dichloride:VPetroleum ether10:4), the remaining material was purified by column chromatography to obtain compound 005(13.28g, yield: 76.18%, Mw: 666.81).
Figure GDA0003660117880000111
The detection analysis was performed on the obtained compound-005, and the results were as follows:
1) HPLC purity > 99%.
2) Mass spectrum testing:
a theoretical value of 666.82; the test value was 666.81.
3) Elemental analysis:
the calculated values are: c, 88.26; h, 5.14; n, 4.20; o, 2.40;
the test values are: c, 88.25; h, 5.15; n, 4.21; o, 2.39.
Example 2: synthesis of Compound-059
1. Under the protection of nitrogen, dissolving a raw material A-059(30.00mmol) and a raw material B-059(30.00mmol) in 250.00ml of toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.3mmol), tri-tert-butylphosphine (1.5mmol) and sodium tert-butoxide (60.00mmol), stirring uniformly, heating to 90 ℃, and carrying out reflux reaction for 5 hours; after the reaction is finished, slightly cooling to 75 ℃, filtering by using diatomite to remove salt and a catalyst, cooling the filtrate to room temperature, washing by using water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after combining the organic phases, drying was performed using anhydrous magnesium sulfate (35.00g), and the solvent was removed using a rotary evaporator; completely dissolving the solid organic matter by using dichloromethane, slowly dripping the dissolved organic matter into a petroleum ether solution, uniformly stirring, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying (80 ℃ for 4 hours) to prepare an intermediate 1(20.87g, yield: 87.56%);
Figure GDA0003660117880000121
2. Starting material C-059(25.17mmol) was dissolved in 250.00ml of DMF under nitrogen blanket, followed by the addition of intermediate 1(25.17mmol) and potassium carbonate (K)2CO3) (30.20mmol), the mixture was warmed to 100 ℃ and stirred for 20 h; after the reaction is finished, removing the solvent to obtain a solid organic matter; using methylene chloride and petroleum ether (V)Methylene dichloride:VPetroleum ether10:4), and the remaining substance was purified by column chromatography to obtain chemical formula 1(17.36g, yield: 76.22%, Mw: 905.21).
Figure GDA0003660117880000122
The detection analysis was performed on the obtained compound-59, and the results were as follows:
1) HPLC purity > 99%.
2) Mass spectrometry test: a theoretical value of 905.24; the test value was 905.21.
3) Elemental analysis:
the calculated values are: c, 84.92; h, 6.68; n, 3.09; o, 1.77; s, 3.54;
the test values are: c, 84.93; h, 6.67; n, 3.08; o, 1.76; and S, 3.56.
Example 3: synthesis of Compound-069
1. Under the protection of nitrogen, dissolving a raw material A-069(30.00mmol) and a raw material B-069(30.00mmol) in 200.00ml of a toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.3mmol), tri-tert-butylphosphine (1.5mmol) and sodium tert-butoxide (60.00mmol), uniformly stirring, heating to 90 ℃, and carrying out reflux reaction for 5 hours; after the reaction is finished, slightly cooling to 75 ℃, filtering by using diatomite to remove salt and a catalyst, cooling the filtrate to room temperature, washing by using water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after combining the organic phases, drying was performed using anhydrous magnesium sulfate (30.00g), and the solvent was removed using a rotary evaporator; completely dissolving the solid organic matter by using dichloromethane, slowly dripping the dissolved organic matter into a petroleum ether solution, uniformly stirring, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying (80 ℃ for 4 hours) to prepare an intermediate 1(15.62g, yield: 87.66%);
Figure GDA0003660117880000131
2. Starting material C-069(25.25mmol) was dissolved in 180.00ml of DMF under nitrogen protection, followed by addition of intermediate 1(25.25mmol) and potassium carbonate (K)2CO3) (30.30mmol), the mixture was warmed to 100 ℃ and stirred for 20 h; after the reaction is finished, removing the solvent to obtain a solid organic matter; using methylene chloride and petroleum ether (V)Methylene dichloride:VPetroleum ether10:4), and the remaining substance was purified by column chromatography to obtain chemical formula 1(12.79g, yield: 76.15%, Mw: 664.85).
Figure GDA0003660117880000132
The compound-069 obtained was analyzed for detection, and the results were as follows:
1) HPLC purity > 99%.
2) Mass spectrometry test:
a theoretical value of 664.87; the test value was 664.85.
3) Elemental analysis:
the calculated values are: c, 83.10; h, 5.46; n, 4.21; o, 2.41; s, 4.82;
the test values are: c, 83.11; h, 5.45; n, 4.22; o, 2.40; and S, 4.82.
Example 4: synthesis of Compound-087
1. Under the protection of nitrogen, dissolving a raw material A-087(30.00mmol) and a raw material B-087(30.00mmol) in 200.00ml of a toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.3mmol), tri-tert-butylphosphine (1.5mmol) and sodium tert-butoxide (60.00mmol), uniformly stirring, heating to 90 ℃, and carrying out reflux reaction for 5 hours; after the reaction is finished, slightly cooling to 75 ℃, filtering by using diatomite to remove salt and a catalyst, cooling the filtrate to room temperature, washing by using water for three times to keep an organic phase, and extracting an aqueous phase by using ethyl acetate; after combining the organic phases, drying was performed using anhydrous magnesium sulfate (30.00g), and the solvent was removed using a rotary evaporator; completely dissolving the solid organic matter by using dichloromethane, slowly dripping the dissolved organic matter into a petroleum ether solution, uniformly stirring, separating out a precipitate, performing suction filtration to obtain a solid, sequentially leaching by using absolute ethyl alcohol and petroleum ether, and drying (80 ℃ for 4 hours) to prepare an intermediate 1(16.30g, yield: 87.59%);
Figure GDA0003660117880000141
2. Under the protection of nitrogenStarting material C-087(25.80mmol) was dissolved in 220.00ml of DMF solution, followed by the addition of intermediate 1(25.80mmol) and potassium carbonate (K)2CO3) (30.30mmol), the mixture was warmed to 100 ℃ and stirred for 20 h; after the reaction is finished, removing the solvent to obtain a solid organic matter; using methylene chloride and petroleum ether (V)Methylene dichloride:VPetroleum ether10:4), and the remaining substance was purified by column chromatography to obtain chemical formula 1(15.12g, yield: 76.19%, Mw: 769.04).
Figure GDA0003660117880000151
The compound-087 obtained was analyzed for detection, and the results were as follows:
1) HPLC purity > 99%.
2) Mass spectrometry test:
a theoretical value of 769.06; the test value was 769.04.
3) Elemental analysis:
the calculated values are: c, 85.90; h, 6.29; n, 3.64; s, 4.17;
the test values are: c, 85.91; h, 6.28; n, 3.65; and S, 4.16.
The general structural formula is chemical formula 1 in the summary of the invention, and the synthetic routes and principles of other compounds are the same as those of the above-listed examples, so the general structural formula is not exhaustive here. In examples 5 to 10 of the present invention, dibenzo-seven-membered heterocyclic compounds shown in table 1 below can be obtained according to the above preparation method:
table 1:
Figure GDA0003660117880000152
Figure GDA0003660117880000161
Figure GDA0003660117880000171
the compounds synthesized in the above examples were also tested for their glass transition temperature (Tg) using a TMA4000 thermomechanical analyzer, as shown in table 2:
TABLE 2
Compound (I) Glass transition temperature (Tg) Compound (I) Glass transition temperature (Tg)
5 168.3 69 168.8
20 170.5 78 170.9
38 169.2 87 172.6
42 171.4 93 171.7
59 172.1 99 169.7
As can be seen from the glass transition temperatures of the compounds disclosed in table 2, the compounds prepared by the present disclosure have relatively high thermal transition temperatures to illustrate the high thermal stability of the materials.
In addition, in order to further illustrate the application effect of the dibenzo-seven-membered heterocyclic compound prepared by the present disclosure in an electroluminescent device, the inventors further performed the following test experiments, specifically as follows:
device example 1:
the structure of the prepared OLED device is as follows: ITO (indium tin oxide) -Ag-ITO (indium tin oxide) anode/HIL/HTL/EML/ETL/EIL/cathode/light extraction layer.
a. An ITO anode: coating with a thickness of
Figure GDA0003660117880000181
The ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate is cleaned in distilled water for 2 times, ultrasonically cleaned for 30min, then repeatedly cleaned for 2 times by distilled water, ultrasonically cleaned for 10min, and after the cleaning is finished, ultrasonically cleaned by methanol, acetone and isopropanol in sequence (each time for 5min), dried, then transferred into a plasma cleaning machine for cleaning for 5min, and then sent into an evaporation machine, and other functional layers are evaporated on the substrate by taking the substrate as an anode in sequence.
b. HIL (hole injection layer): a hole injection layer was formed by evaporation of 2-TNATA (N1- (2-naphthyl) -N4, N4-bis (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenylbenzene-1, 4-diamine) at 10 nm.
c. HTL (hole transport layer): a hole transport layer was formed by depositing 00515nm of the compound prepared in example 1.
d. EML (light-emitting layer): the host material EMH-1 and the doping material EMD-1 are mixed and evaporated by weight ratio of 97: 3 for 40nm to form a luminescent layer. Wherein the structural formulas of the host material EMH-1 and the doping material EMD-1 are as follows;
f. ETL (electron transport layer): and evaporating ET-1 and Liq 40nm to form an electron transport layer. Wherein the weight ratio of ET-1 to Liq is 60:40, wherein the structural formula of ET-1 is shown as follows;
g. EIL (electron injection layer): and depositing Yb at 1.0nm to form an electron injection layer.
h. Cathode: and (4) evaporating and plating magnesium and silver at 18nm in a weight ratio of 1:9 to obtain the OLED device.
i. Light extraction layer: IDX001 was vacuum-deposited on the cathode to a thickness of 70nm as a light extraction layer.
Figure GDA0003660117880000182
Device embodiments 2 to 10: according to the method of the device example 1, compounds-020, 038, 042, 059, 069, 078, 087, 093 and 099 are respectively selected to replace the compound-005, evaporation of the hole transport layer is carried out, and corresponding organic electroluminescent devices are prepared and are respectively marked as device examples 2 to 10.
Device comparative example 1:
the only difference between the preparation method of the organic electroluminescent device and the device example 1 is that the organic electroluminescent device is prepared by selecting a compound TCTA to replace a hole transport material (compound-005) in the device example 1 for evaporation, and the corresponding organic electroluminescent device is marked as a device comparative example 1. Wherein, the chemical structural formula of TCTA is:
Figure GDA0003660117880000191
The organic electroluminescent devices obtained in the device examples 1 to 15 and the device comparative examples 1 to 2 were characterized at a luminance of 6000(nits), and the test results were as follows:
TABLE 3
Figure GDA0003660117880000192
Figure GDA0003660117880000201
From the results of table 3 above, it can be confirmed that the organic electroluminescent device using the dibenzo-seven-membered heterocyclic compound provided by the present invention as a hole material exhibits high luminous efficiency and long service life, particularly: the dibenzo-seven-membered heterocyclic compound is suitable for a cavity layer, and the efficiency and the service life of the dibenzo-seven-membered heterocyclic compound are obviously improved compared with those of a comparative compound 1 and TCTA.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (5)

1. A dibenzo-seven-membered heterocyclic compound is characterized in that the structural general formula of the compound is as follows:
Figure FDA0003660117870000011
Wherein X represents a bond, and X is-O-or-S-;
l is a connecting bond, and L is a substituted or unsubstituted C6-C30 arylene, said substituent being deuterium or aryl;
Ar1and Ar2Are the same substituent or different substituents; and Ar1And Ar2At least one selected from the following groups: substituted or unsubstituted C6-C30 aryl, substitutedOr unsubstituted 3-to 30-membered heteroaryl, said substituent being alkyl or aryl;
R1and R2Are the same substituent or different substituents; and R is1And R2At least one selected from the following groups: hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, the substituent being alkyl or aryl.
2. A process for the preparation of a dibenzo-seven-membered heterocyclic compound according to claim 1, which comprises the steps of:
(1) under the protection of nitrogen, dissolving the raw material A and the raw material B in a toluene solution, adding a palladium catalyst, a phosphine ligand and sodium tert-butoxide, uniformly stirring, heating and refluxing to prepare an intermediate 1;
(2) under the protection of nitrogen, dissolving a raw material C in a DMF solution, then adding an intermediate 1 and potassium carbonate, and uniformly stirring to prepare a dibenzo-heptatomic heterocyclic compound shown as a chemical formula 1;
The preparation reaction formula of the dibenzo seven-membered heterocyclic compound is as follows:
Figure FDA0003660117870000012
3. the method for preparing a dibenzo-seven-membered heterocyclic compound according to claim 2, wherein the molar ratio of the raw material A to the raw material B is 1: 1, adding the palladium catalyst, the phosphine ligand and sodium tert-butoxide in a molar ratio of 1: 5: 200.
4. the method for preparing a dibenzo-seven-membered heterocyclic compound according to claim 2, wherein the molar ratio of the raw material C, the intermediate 1 and the potassium carbonate added is 5: 5: 6.
5. use of the dibenzo-seven-membered heterocyclic compound according to claim 1 or the dibenzo-seven-membered heterocyclic compound prepared by the preparation method according to claim 2 as a hole transport material in an organic electroluminescent device.
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