CN114621241A - Compound with triazine benzofuran structure as core framework and application thereof - Google Patents
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Abstract
The invention relates to a compound taking a triazine benzofuran structure as a core framework and application thereof, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (1), wherein in the general formula (1), R1、R2Each independently represents substituted or unsubstituted C6‑C30Aryl, a structure represented by general formula (2) or general formula (3); and R is1、R2At least one of the two is represented by a structure shown in a general formula (2) or a general formula (3); r3Represented by a structure represented by a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11); the compound of the present invention has a triazine and benzofuran fused ring structureBy optimizing the structure of the device, the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a compound taking a triazine benzofuran structure as a core framework and application thereof.
Background
The organic electroluminescent device includes an anode, a cathode, and an organic functional layer including a light emitting layer disposed between the anode and the cathode, wherein the organic functional layer is a general term for each layer between the cathode and the anode. In addition, a hole transport region may exist between the anode and the light emitting layer, and an electron transport region may exist between the light emitting layer and the cathode. Holes from the anode may migrate through the hole transport region to the light emitting layer, and electrons from the cathode may migrate through the electron transport region to the light emitting layer. Carriers (e.g., holes and electrons) recombine in the light emitting layer and generate excitons. According to the quantum mechanics principle, the organometallic compound material as the doping material can realize 100% internal quantum yield.
Nevertheless, there is still a need for improvements in device voltage, current efficiency and lifetime for triplet-emissive phosphorescent OLEDs. In particular, higher requirements are placed on the host and dopant materials in the light-emitting layer. Among these, the properties of the host material generally greatly affect the above-mentioned key properties of the organic electroluminescent device.
According to the prior art, carbazole-based derivatives are generally used as phosphorescent-doped hole-type host materials, and triazine-based derivatives are generally used as phosphorescent-doped electron-type host materials. The performance of the electronic host material has a significant influence on the above-mentioned key performance of the organic electroluminescent device, and the existing electronic host material has a need for improvement in device voltage, efficiency, and especially device lifetime. The present invention provides an electronic-type host substitute material having a low voltage, a high efficiency, and particularly a longer lifetime.
For phosphorescent OLEDs, the use of a single host for the emissive layer typically results in an imbalance of holes and electrons, a severe roll-off in device efficiency at high current densities and a shortened lifetime. The invention also provides a combination of two main body materials, which can effectively solve the defects of the single-main-body device.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides a compound with a triazinylbenzofuran structure as a core skeleton and an application thereof. The compound has a triazine and benzofuran fused ring structure, and can effectively improve the photoelectric performance of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme of the invention is as follows:
a compound taking a triazine benzofuran structure as a core skeleton is disclosed, wherein the structure of the compound is shown as a general formula (1):
in the general formula (1), R1、R2Each independently represents substituted or unsubstituted C6-C30Aryl, a structure represented by general formula (2) or general formula (3); and R is1、R2At least one of the two is represented by a structure shown in a general formula (2) or a general formula (3);
R3represented by a structure represented by a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11);
in the general formula (2), X1Is represented by O or N-Ar5；
In the general formula (2), the general formula (3), the general formula (8) and the general formula (9), L1、L2、L3、L4Each independently represents a single bond, substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroarylenes;
in the general formula (6), the general formula (7), the general formula (10) and the general formula (11), Ar1-Ar4Each independently represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroaryl;
Ar5is represented by substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroaryl;
in the general formula (2) -the general formula (11), R4-R16Each independently represents hydrogen, deuterium, tritium, a halogen atom, cyano, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroaryl;
said "substituted or unsubstituted" substituents being optionally selected from deuterium, tritium, halogen atoms, cyano, C6-C30Aryl, C containing one or more hetero atoms2-C30One or more of heteroaryl;
the heteroatom is selected from nitrogen, oxygen or sulfur.
Preferred embodiment, the above C6-C30The aryl is selected from one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl and pyrenyl;
said C is6-C30The arylene group is any one selected from phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene and pyrenylene;
said C is2-C30Heteroaryl is selected from one of pyridyl, pyrimidyl, quinolyl, naphthyridinyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl and N-phenylcarbazolyl;
said C is2-C30The heteroarylene group is selected from pyridylene, pyrimidylene, quinolylene, naphtylene, furylene, thienylene, dibenzofuranylene, dibenzothiophenylene, carbazolyl, and N-phenylcarbazolylOne or more of azolyl;
the substituent of the substituted or unsubstituted is one or more of deuterium, tritium, fluorine atom, cyano, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl and pyridyl.
Preferred embodiment, R1、R2Each independently represented by any one of the following structures:
preferred embodiment, R3Represented as any one of the following structures:
preferably, the specific structure of the compound is any one of the following structures:
an organic electroluminescent device comprises a cathode, an anode and functional layers, wherein the functional layers are positioned between the cathode and the anode, and at least one functional layer in the organic electroluminescent device contains the compound taking a triazine benzofuran structure as a core skeleton.
Preferably, the functional layer includes a light-emitting layer containing the compound having the triazinylbenzofuran structure as a core skeleton.
A lighting or display element comprising the organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
the compound has the advantages that the distribution of LUMO is fully delocalized due to pi conjugate effect and a rigid plane, so that the compound has strong electron transmission capacity, high radiation transition rate and good excited state stability;
the compound provided by the invention has deep HOMO and LUMO energy levels, and the higher T1 energy level can ensure the energy transfer efficiency between the host and the guest, and can effectively improve the exciton utilization efficiency when being used as a host material of a light-emitting layer;
the compound has the characteristics of strong group rigidity, difficult intermolecular crystallization and aggregation, good film forming property, high glass transition temperature and thermal stability. Therefore, when the compound is applied to an OLED device, the stability of a film layer formed by the material can be kept, and the service life of the OLED device is prolonged.
After the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
Detailed Description
The raw materials involved in the synthesis examples of the present invention were purchased from Zhongjieyanwang Limited.
Preparation example 1 Synthesis of intermediate A1
Under a nitrogen environment, adding raw material C1(10mmol) and anhydrous THF (15mL) into a flask, reducing the reaction temperature to 0 ℃, slowly adding an n-hexane solution of 11mmol n-butyllithium under stirring, slowly returning to room temperature after reacting for 3h, then adding raw material D1(11mmol), and continuing to stir for 24h until the reaction is completed; the organic layer was extracted with ethyl acetate, dried and separated by column chromatography to give intermediate a 1.
Preparation example 2 Synthesis of intermediate A8
In a nitrogen-blanketed flask, starting material C1(20mmol), starting material D2(24mmol), Pd (PPh)3)4(1.0mmol) and K2CO3(50mmol) in toluene, ethanol and H2After the mixture of O, the mixture was refluxed at 120 ℃ for 24 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, dried and separated by column chromatography to give intermediate A8.
Example 3 Synthesis of intermediate B1
(1) Starting materials E1(4mmol), 2-hydroxyphenylboronic acid (6mmol), (amphos)2PdCl2(400. mu. mol) and potassium carbonate (12mmol) were added together to 80ml of 1, 4-dioxane and 15ml of water to form a suspension, which was then heated to 90 ℃ with stirring for 12 h; cooling to room temperature after the reaction is finished, concentrating the solvent, extracting by ethyl acetate, washing, drying, filtering, spin-drying to obtain a crude product, and separating by column chromatography to obtain a pure product; dissolving the obtained pure product (3.6mmol) in 40ml dichloromethane, slowly adding m-CPBA (7.5mmol) at 0 ℃, returning to room temperature after the addition, stirring for 5h, extracting the mixed solution after the reaction is finished by ethyl acetate, washing, drying, filtering, spin-drying to obtain a crude product, and separating by column chromatography to obtain a pure product of an intermediate F1;
(2) the resulting intermediate F1(1.6mmol), CsCO3(3.2mmol) is suspended in 120ml DMSO solvent and heated to 80 ℃ to react for 1h, after the reaction is finished, the solution is cooled to room temperature, the solvent is concentrated and then extracted by ethyl acetate, washed, dried, filtered and spin-dried to obtain a crude product, and then the crude product is separated by column chromatography to obtain a pure product of an intermediate G1;
(3) the resulting intermediate G1(1.0mmol), pinacol boronate (1.2mmol), potassium acetate (4.0mmol) and PdCl in a nitrogen-blanketed flask2(dppf) (0.02mmol) is added into 25ml of DMF solvent together, heated to 80 ℃ and stirred for 24h, cooled to room temperature after the reaction is finished, the solvent is concentrated, extracted by ether, washed, dried, filtered and dried by spinning to obtain a crude product, and then the crude product is separated by column chromatography to obtain a pure product of an intermediate B1.
The synthetic steps of the intermediates B2/B4/B5-B8 are similar to the synthetic steps of the intermediate B1, only part of raw materials are replaced, and the synthetic method of the intermediate B1 can be referred.
Preparation example 4 Synthesis of intermediate B3
In a nitrogen-protected flask, raw material I (1.2mmol), aniline (1mmol) and Pd2(dba)3(0.11mmol), RuPhos (0.33mmol) and sodium tert-butoxide (3.1 mm)ol) is added into 8ml of anhydrous dimethylbenzene, the temperature is raised to 120 ℃, the mixture is stirred and reacted for 20 hours, the mixture is cooled to room temperature after the reaction is finished, a crude product is obtained after the solvent is concentrated and extracted by dichlorohexane, washed, dried, filtered and dried in a spinning mode, and then the pure product of the intermediate B3 is obtained through column chromatography separation.
EXAMPLE 1 Synthesis of Compound 2
In a nitrogen-blanketed flask, intermediate A1(40mmol), intermediate B1(48mmol), Pd (PPh)3)4(2.0mmol) and K2CO3(100mmol) was dissolved in a mixture of toluene and ethanol, and the mixture was refluxed at 120 ℃ for 24 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, dried and separated by column chromatography to obtain compound 2.
Examples 2-20 below refer to the same reaction types as example 1, the same reactants appear in different examples using different reference numbers, and the test results of the starting materials A and B and the prepared compounds referred to in examples 1-20 are shown in Table 1.
TABLE 1
Mass spectral data of the intermediates prepared above are shown in Table 2
TABLE 2
The nmr hydrogen spectrum data of the compound prepared above are shown in table 3;
TABLE 3
The compound of the present invention is used in a light-emitting device, and can be used as a material for a light-emitting layer. The physicochemical properties of the compounds prepared in the above examples of the present invention were measured, and the results are shown in table 4:
TABLE 4
Note: the triplet energy level T1 was measured by the Fluorolog-3 series fluorescence spectrometer from Horiba under the conditions of 2 x 10-5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is in an atmospheric environment; eg was measured by a two-beam uv-vis spectrophotometer (model: TU-1901), LUMO ═ HOMO-Eg.
The data in the table show that the organic compound has high glass transition temperature, can be applied to improving the phase stability of material films and further prolonging the service life of devices; the organic compound of the present invention has appropriate HOMO and LUMO energy levels, so that the problem of carrier injection can be solved, and the device voltage can be reduced. The organic compound has a high T1 energy level, and can ensure the energy transfer efficiency between a host and an object when used as a host material. Therefore, after the organic material is applied to different functional layers of an OLED device, the voltage of the device can be effectively reduced, and the service life of the device can be prolonged.
The effect of the synthesized OLED material of the present invention in the application of the device is detailed below by device examples 1-28 and device comparative examples 1-3. Compared with the device example 1, the device examples 2 to 28 and the device comparative examples 1 to 3 of the present invention have the same manufacturing process, adopt the same substrate material and electrode material, and keep the film thickness of the electrode material consistent, except that the luminescent layer material in the device is replaced.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2(ITO (15nm)/Ag (150nm)/ITO (15nm)) is washed, that is, washed with a detergent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 were deposited by a vacuum deposition apparatus as the hole injection layer 3, and the film thickness was 10nm, and the mass ratio of HT-1 to P-1 was 97: 3. HT-1 was then evaporated as a hole transport layer 4 to a thickness of 130 nm. EB-1 was subsequently evaporated as an electron blocking layer 5 with a thickness of 40 nm. After the evaporation of the electron barrier layer material is finished, the light-emitting layer 6 of the OLED light-emitting device is manufactured, and the structure of the light-emitting layer 6 comprises that the compound 2 used by the OLED light-emitting layer 6 is used as a main body material, GD-1 is used as a doping material, the doping proportion of the doping material is 6% (mass ratio), and the thickness of the light-emitting layer is 40 nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated at a mass ratio of ET-1 to Liq of 1:1 and a film thickness of 35nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce a 15 nm-thick Mg: the Ag electrode layer is used as a cathode layer 10, and the mass ratio of Mg to Ag is 1: 9. On the cathode layer 10, CP-1 was vacuum-deposited as the CPL layer 11, and the thickness was 70 nm. The organic electroluminescent device 1 is obtained.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected by a known driving circuit, and the voltage, current efficiency, light emission spectrum, and lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 5, in which the electron blocking layer and light emitting layer doping materials of green device examples 2-18, 27, device comparative examples 1-2, 4-5 are the same as device example 1; the electron blocking layers of the red light device examples 19 to 26 and 28 and the device comparative examples 3 and 6 were replaced with EB-2 in comparison with the device example 1, and the film thickness was 90nm, the light emitting layer doping material was replaced with RD-1 in comparison with the device example 1, and the doping ratio was 3% (mass ratio), and the other layer materials were kept the same; voltage, current efficiency, color and 20mA/cm of the resulting device2The following LT95 life test results are shown in table 6.
TABLE 5
TABLE 6
Note: the voltage, current efficiency and color coordinates were measured at a current density of 10mA/cm2Tested under conditions using an IVL (current-voltage-brightness) test system (frastd scientific instruments ltd, su); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to a linear vibration at 20mA/cm2The time it takes for the device luminance to decay to 95%.
As can be seen from the device data results in Table 6, compared with the device comparative examples 1-2 and 4-5, the device examples 1-18 and 27 of the present invention have greatly improved device efficiency and device lifetime, especially greatly reduced device voltage; compared with comparative device examples 3 and 6, device examples 19 to 26 and 28 of the present invention have certain improvements in device efficiency and lifetime, and the device voltage is reduced to a small extent.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A compound taking a triazine benzofuran structure as a core skeleton is characterized in that the structure of the compound is shown as a general formula (1):
in the general formula (1), R1、R2Each independently represents substituted or unsubstituted C6-C30Aryl, a structure represented by general formula (2) or general formula (3); and R is1、R2At least one of the two is represented by a structure shown in a general formula (2) or a general formula (3);
R3represented by a structure represented by a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11);
in the general formula (2), X1Is represented by O or N-Ar5；
In the general formula (2), the general formula (3), the general formula (8) and the general formula (9), L1、L2、L3、L4Each independently represents a single bond, substituted or unsubstituted C6-C30Arylene, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroarylenes;
in the general formula (6), the general formula (7), the general formula (10) and the general formula (11), Ar1-Ar4Each independently represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroaryl;
Ar5is represented by substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroaryl;
in the general formula (2) -the general formula (11), R4-R16Each independently represents hydrogen, deuterium, tritium, a halogen atom, cyano, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms2-C30One of heteroaryl;
said "substituted or unsubstituted" substituents being optionally selected from deuterium, tritium, halogen atoms, cyano, C6-C30Aryl, C containing one or more hetero atoms2-C30One or more of heteroaryl;
the heteroatom is selected from nitrogen, oxygen or sulfur.
2. The compound of claim 1, wherein C is6-C30The aryl is selected from one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl and pyrenyl;
said C is6-C30The arylene group is any one selected from phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene and pyrenylene;
said C is2-C30Heteroaryl is selected from one of pyridyl, pyrimidyl, quinolyl, naphthyridinyl, furyl, thienyl, dibenzofuryl, dibenzothienyl, carbazolyl and N-phenylcarbazolyl;
said C is2-C30The heteroarylene group is selected from one or more of pyridylene, pyrimidylene, quinolylene, naphtylene, furylene, thienylene, dibenzofuranylene, dibenzothiophenylene, carbazolyl and N-phenylcarbazolyl;
the substituent of the substituted or unsubstituted is one or more of deuterium, tritium, fluorine atom, cyano, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl and pyridyl.
3. A compound of claim 1, wherein R is1、R2Each independently represented by any one of the following structures:
4. a compound of claim 1, wherein R is3Represented as any one of the following structures:
5. the compound of claim 1, wherein the specific structure of the compound is any one of the following structures: .
6. An organic electroluminescent device comprising a cathode, an anode and functional layers, wherein the functional layers are positioned between the cathode and the anode, characterized in that at least one functional layer in the organic electroluminescent device comprises the compound with the triazine benzofuran structure as the core skeleton in any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the functional layer comprises a light-emitting layer, and the light-emitting layer contains the compound having a triazinylbenzofuran structure as a core skeleton according to any one of claims 1 to 5.
8. A lighting or display element comprising the organic electroluminescent device according to any one of claims 6 to 7.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114685454A (en) * | 2020-12-29 | 2022-07-01 | 广州华睿光电材料有限公司 | Organic compound, mixture, composition and organic electronic device |
| CN115109070A (en) * | 2021-03-19 | 2022-09-27 | 烟台显华科技集团股份有限公司 | Compound containing indolo-heterocyclic structure and application thereof |
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| KR20200077880A (en) * | 2018-12-21 | 2020-07-01 | 두산솔루스 주식회사 | Organic compound and organic electroluminescent device using the same |
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| CN114685454A (en) * | 2020-12-29 | 2022-07-01 | 广州华睿光电材料有限公司 | Organic compound, mixture, composition and organic electronic device |
| CN114685454B (en) * | 2020-12-29 | 2024-01-12 | 广州华睿光电材料有限公司 | Organic compounds, mixtures, compositions and organic electronic devices |
| CN115109070A (en) * | 2021-03-19 | 2022-09-27 | 烟台显华科技集团股份有限公司 | Compound containing indolo-heterocyclic structure and application thereof |
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