CN113248522B - Organic compound and organic light-emitting device using same - Google Patents
Organic compound and organic light-emitting device using same Download PDFInfo
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Abstract
An organic compound and an organic light emitting device using the same, the organic compound having a structural formula shown in fig. 1:
in the above structural formula, ar 1 Selected from substituted or unsubstituted C6-C90 heteroaryl or heterocyclyl groups containing more than two nitrogen atoms; x 1 And X 2 Represents a single bond, oxygen (O), sulfur (S), sulfur Oxide (SO) or sulfur dioxide (SO) 2 )；R 1 And R 2 Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative; l is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
Description
Technical Field
The present invention relates to an organic compound and an organic light emitting device using the same, and more particularly, to a soluble organic compound having excellent color purity and high brightness and high luminous efficiency and an OLED device using the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The OLED has a series of advantages of autonomous light emission, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from positive and negative electrodes and then migrate, recombine and attenuate in an organic material to generate light emission. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been commercially used due to their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to the triplet energy level higher than that of the guest materials, which prevents the energy reverse transfer of exciton transition release. Currently, materials having both high triplet energy levels and good hole mobility in the host material are still lacking. Therefore, how to design a new main material with better performance is a problem to be solved urgently by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic compound having excellent pure chromaticity, high luminance and excellent luminous efficiency, and an organic light emitting device using the same
The invention provides an organic compound, the structural formula of which is shown as 1,
in the above structural formula, ar 1 Selected from substituted or unsubstituted C6-C90 heteroaryl or heterocyclyl groups comprising two or more nitrogen atoms;
X 1 and X 2 Represents a single bond, oxygen (O), sulfur (S), sulfur Oxide (SO) or sulfur dioxide (SO) 2 )；
R 1 And R 2 Each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative;
l is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
Preferably, an organic compound characterized by: the structural formula is shown as 1-6:
in the above structural formula, ar 1 Selected from substituted or unsubstituted C6-C90 heteroaryl or heterocyclyl groups containing more than two nitrogen atoms; x 1 And X 2 Represents a single bond, oxygen (O), sulfur (S), sulfur Oxide (SO) or sulfur dioxide (SO) 2 )；
R 1 And R 2 Each independently selected from substituted or unsubstituted C6-C30 aryl substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative;
l is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
Further preferably, ar in the structure of the organic compound is Ar 1 And Ar 2 Independently selected from the following structures:
wherein R is 5 、R 6 And R 7 Independently selected from one of hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
X 1 、X 2 、X 3 independently selected from nitrogen (N) or carbon (C);
L 1 is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
In a further preferred embodiment, R in the structure of the organic compound is 1 And R 2 Independently selected from the following structures:
wherein R is 8 、R 9 And R 10 Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
L 2 is a single bond or is selected from substituted or unsubstituted C1-C30 aryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C4-C30 heteroaryl.
Further preferred is when the organic compound is independently selected from the group consisting of:
the invention also provides application of the heterocyclic series-containing compound in an organic light-emitting device.
Preferably, the organic light emitting device comprises an anode, a cathode and a plurality of organic functional layers positioned between the anode and the cathode, wherein the organic functional layers contain the compound containing the heterocyclic series.
The invention has the beneficial effects that:
the invention provides a heterocyclic series-containing compound, which has a structure shown in a formula 1, wherein the electron-rich structure in the heterocyclic series-containing compound has great influence on the photoelectric property of the whole compound molecule, so that unnecessary vibration energy loss is reduced, and high-efficiency luminous performance is realized. By adjusting substituent groups, the compound has better thermal stability and chemical properties. The compound containing carbazole series has the advantages of simple preparation method and easily obtained raw materials, and can meet the industrial requirements.
The carbazole series compounds are prepared into devices, particularly used as main materials, the devices have the advantages of low driving voltage and high luminous efficiency, and are superior to the conventional common OLED devices.
In the present invention, the organic electroluminescent device preferably includes an anode, a cathode, and several organic layers located between the anode and the cathode, and the "organic layer" refers to a term of all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole characteristic and a layer having an electron characteristic. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a functional layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the hole transport layer may be formed of a conventional hole injection material, a hole transport material, or a material having both hole injection and hole transport functions, in addition to the electron-generating material.
For example, the organic layer includes a light emitting layer, and the light emitting layer includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. In the present invention, the compound for an organic electroluminescent device can be used as a fluorescent host, can also be used as a fluorescent dopant, and can be used as a fluorescent host and a fluorescent dopant at the same time.
In the present invention, the light emitting layer may be a red, yellow or blue light emitting layer. In the present invention, when the light-emitting layer is a light-emitting layer, an organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-mentioned compound for an organic electroluminescent device as a host.
In the present invention, the organic electroluminescent diode device of the organic compound is characterized in that the organic electroluminescent diode device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially deposited, and the organic compound is used as a host material of the light emitting layer.
The present invention is not particularly limited in the method for preparing the organic electroluminescent device, and may be prepared by using a method and materials for preparing a light emitting device, which are well known to those skilled in the art, in addition to the organic compound of formula 1.
Detailed Description
In order to make the technical means, the creation features, the achievement purposes and the effects of the invention easy to understand, the invention is further described with reference to specific embodiments.
Example 1: synthesis of Compound 1-2
1. Synthesis of intermediate 1-2
In a 250 ml three-necked flask were added intermediate 1-1 (6.41 g, 20 mmol), N- (4-bromophenyl) -N-phenylbenzamide 6.81 g, 21.0 mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8 g, 33.6 mmol) and o-xylene (80 ml). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column to obtain Compound 1-2 (5.07 g, yield 45%). LC-MS: M/Z563.15 (M + H) + 。
2. Synthesis of Compound 1
In a 250 ml three-necked flask were added intermediate 1-2 (11.27 g, 20 mmol), a (5.05 g, 21.0 mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8 g, 33.6 mmol) and o-xylene (80 ml). The temperature of the reaction system is raised to 120 ℃, and the reaction is carried out for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to obtain a crude product, which was then subjected to silica gel column to obtain Compound 1 (7.66 g, yield 50%). LC-MS: M/Z765.23 (M + H) + 。
Example 2: synthesis of Compound 7
Compound 7 was synthesized by the method of reference example 1 to give compound 7 (8.37 g, yield 55%). LC-MS: M/Z767.22 (M + H) + 。
Example 3: synthesis of Compound 8
Compound 8 was synthesized by the method of reference example 1 to give compound 8 (11.25 g, yield 56%). LC-MS: M/Z843.25 (M + H) + 。
Example 4: synthesis of Compound 150
Compound 150 was synthesized by the method of reference example 1 to give compound 150 (8.24 g, yield 52%). LC-MS: M/Z767.25 (M + H) +.
Example 5: synthesis of Compound 9
Compound 9 was synthesized by the method of reference example 1 to give compound 26 (4.3 g, yield 49%). LC-MS: M/Z794.23 (M + H) +.
Example 6: synthesis of Compound 11
Compound 11 was synthesized by the method of reference example 1 to give compound 11 (5.7 g, yield 46%). LC-MS: M/Z870.26 (M + H) +.
Example 7: synthesis of Compound 241
Compound 241 was synthesized by the method of reference example 1 to obtain compound 241 (6.8 g, yield 49%). LC-MS: M/Z703.27 (M + H) + 。
Evaluation example 1: HOMO, LUMO, triplet energy level, and S1-T1 energy level evaluation of the compound:
the above data show that the HOMO value of the substance is reduced after the amine-series compound is introduced into the compound, the Eg (eV) value conforms to the RH (phosphorescent red host) condition, and the delayed fluorescence property (S) is exhibited after the amine-series compound is introduced into the compound 1 -T 1 ) And (5) strengthening.
Device embodiments
(I) Evaluation of luminescent Material devices
The compounds of the respective organic layers used in the device examples are as follows:
1. first embodiment
The ITO glass substrate was patterned to have a light emitting area of 3 mm × 3 mm. The patterned ITO glass substrate was then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10 -6 And (4) supporting. Thereafter on an ITO substrate
Compound(s)>
And &>
The sequence of (a) and (b) forming layers of organic material.
2. Second embodiment
An organic light-emitting device of the second embodiment was fabricated in the same manner as in the first embodiment above, except that the host material layer of the organic light-emitting device was replaced with compound 7 from compound 1 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the third embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 8 from compound 1 of the first embodiment.
4. Fourth embodiment
An organic light-emitting device of the fourth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 150 from compound 1 of the first embodiment.
5. Fifth embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 9 from compound 1 of the first embodiment.
6. Sixth embodiment
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 11 from compound 1 of the first embodiment.
7. Seventh embodiment
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 241 from compound 1 of the first embodiment.
8. Comparative example 1
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 1 from the compound 1 of the first embodiment.
9. Comparative example 2
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 2 from the compound 1 of the first embodiment.
10. Comparative example 3
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 3 instead of the compound 1 of the first embodiment.
11. Comparative example 4
An organic light-emitting device of comparative example was fabricated in the same manner as in the first embodiment above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 4 instead of the compound 1 of the first embodiment.
12. Comparative example 5
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH5 instead of the compound 1 of the first embodiment.
13. Comparative example 6
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 6 instead of the compound 1 of the first embodiment.
14. Comparative example 7
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 8 instead of the compound 1 of the first embodiment.
15. Comparative example 8
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH 10 instead of the compound 1 of the first embodiment.
The prepared organic light-emitting device is at 10mA/cm 2 Voltage, efficiency and life were tested under current conditions.
Table 1 shows the performance test results of the organic light emitting devices prepared in the examples of the present invention and the comparative examples.
As shown in table 1, the device also operated efficiently at the same voltage. And the current efficiency and life time of the embodiment are remarkably increased compared with the comparative example, for example, the device performance is remarkably improved after introducing amine series groups when comparing example 1 and comparative example 1, example 2 and comparative example 2, example 3 and comparative example 3, example 4 and comparative example 4, example 5 and comparative example 5, example 6 and comparative example 6, example 7 and comparative example 7.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (3)
1. An organic compound characterized by: the organic compound is independently selected from the following compounds:
2. an organic light-emitting device using the organic compound according to claim 1, characterized in that: the organic light-emitting device sequentially comprises a deposited anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein the organic compound is used as a main body material of the light-emitting layer.
3. The organic light-emitting device according to claim 2, wherein the compound according to claim 1 is used alone or in combination with other compounds.
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| CN106467552B (en) * | 2016-08-03 | 2019-02-22 | 江苏三月光电科技有限公司 | A kind of compound containing benzimidazole and its application in OLED device |
| CN107501292A (en) * | 2017-08-28 | 2017-12-22 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device |
| US10844043B2 (en) * | 2018-04-24 | 2020-11-24 | Feng-wen Yen | Heteroaromatic compound and organic electroluminescence device using the same |
| CN110498790B (en) * | 2018-05-16 | 2022-03-01 | 江苏三月科技股份有限公司 | Organic light-emitting composite material and organic electroluminescent device containing same |
| US11760769B2 (en) * | 2019-03-29 | 2023-09-19 | Samsung Electronics Co., Ltd. | Composition and organic light-emitting device including the same |
| CN111943956B (en) * | 2019-05-14 | 2023-06-23 | 江苏三月科技股份有限公司 | Compound taking dibenzo six-membered ring as core, preparation method and application thereof |
| KR20210081966A (en) * | 2019-12-24 | 2021-07-02 | 솔루스첨단소재 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
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