CN113292560B - 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
The present invention provides 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 luminance and high light emitting efficiency, and an OLED device using the same. The structure of the organic compound provided by the invention is shown as a formula 1:in the structural formula, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 aryl, substituted or unsubstituted C10-C30 fused ring groups, substituted or unsubstituted C6-C90 heteroaryl, substituted or unsubstituted C13-C30 amine derivatives (one of which must be a substituted or unsubstituted C6-C90 heteroaryl, heterocyclic group, or substituted or unsubstituted C13-C30 amine derivative containing two or more nitrogen atoms); r is R 1 And R is 2 Is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 aryl group, a substituted or unsubstituted C10-C30 fused ring group, a substituted or unsubstituted C3-C30 heteroaryl group, R 1 And R is 2 May be linked to form a ring.
Description
Technical Field
The present invention relates to an organic compound and an organic light emitting tube device using the same, and more particularly, to a soluble organic compound having excellent color purity and high luminance and high light emitting efficiency, and an OLED device using the same.
Background
With the development of multimedia technology and the improvement of informatization requirements, the requirements on the performance of panel displays are higher and higher. The OLED has a series of advantages of autonomous luminescence, low-voltage direct current drive, full solidification, wide viewing angle, rich colors and the like, and is widely paid attention to potential application in a new-generation display and illumination technology, so that the OLED has a very wide application prospect. The organic electroluminescent device is a spontaneous luminescent device, and the mechanism of OLED luminescence is that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and decay in an organic material under the action of an external electric field to generate luminescence. Typical structures of OLEDs include 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 research progress of organic electroluminescence is very rapid, there are many problems to be solved, such as improvement of External Quantum Efficiency (EQE), design and synthesis of new materials with higher color purity, efficient electron transport, design and synthesis of new materials for hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is a comprehensive reflection of various factors and is also an important index for measuring the quality of the device.
Luminescence can be classified into fluorescence luminescence and phosphorescence luminescence. In fluorescence emission, an organic molecule in a singlet excited state transitions to a ground state, thereby emitting light. On the other hand, in phosphorescence, an organic molecule in a triplet excited state transitions to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been commercially used because of their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to triplet energy levels higher than guest materials, preventing energy back transfer by exciton transition release. Currently, materials that have both high triplet energy levels and good hole mobility in host materials are still lacking. Therefore, how to design new host materials with better performance is always a problem to be solved by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic compound having excellent solid-color, high brightness 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 structural formula, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 fused ring groups, substituted or unsubstituted C6-C90 heteroaryl, substituted or unsubstituted C13-C30 amine derivatives (one of which must be a substituted or unsubstituted C6-C90 heteroaryl, heterocyclic group, or substituted or unsubstituted C13-C30 amine derivative containing two or more nitrogen atoms);
R 1 and R is 2 Is a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C8-C30 fused ring group, a substituted or unsubstituted C3-C30 heteroaryl group, R 1 And R is 2 May be linked to form a ring.
Further preferred is Ar in the organic compound structure 1 And Ar is a group 2 Independently selected from the following structures, but are not meant to be limiting:
wherein R is 3 、R 4 And R is 5 Independently selected from a substituted or unsubstituted C1-C15 alkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-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 a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C8-C30 fused ring group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C13-C30 amine derivative, or a fluorene derivative.
Further preferred is that R in the structure of the organic compound 3 、R 4 And R is 5 Independently selected from one or more of the following structures, but is not meant to be limited thereto:
wherein R is 8 、R 9 、R 10 Independently selected from one of a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, or a combination thereof;
L 2 is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring groups, and substituted or unsubstituted C3-C30 heteroaryl.
Further preferred is that the organic compound is independently selected from the following compounds, but is not meant to be limiting:
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the invention also provides application of the fluorene-containing compounds in organic light-emitting devices.
Preferably, the organic light-emitting device comprises an anode, a cathode and a plurality of organic functional layers between the anode and the cathode, wherein the organic functional layers contain the fluorene-containing compound.
The invention has the beneficial effects that:
the invention provides a fluorene-containing compound which has a structure shown in a formula 1, and the electron-rich structure in the fluorene-containing compound has great influence on the photoelectric property of the whole compound molecule, thereby being beneficial to reducing unnecessary vibration energy loss and realizing high-efficiency luminescence performance. By adjusting substituent groups, the compound has better thermal stability and chemical property. The fluorene-containing compound has the advantages of simple preparation method and readily available raw materials, and can meet the industrial requirements.
The fluorene series compounds are prepared into devices, particularly used as main materials, and the devices have the advantages of low driving voltage and high luminous efficiency, and are superior to the existing common OLED devices.
In the present invention, the organic electroluminescent device preferably comprises an anode, a cathode and several organic layers between the anode and the cathode, the term "organic layer" referring to all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole property and a layer having an electron property. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a 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 layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the hole injection and transport layer may be formed of a conventional hole injection material, a conventional hole transport material, or a conventional hole injection and transport material, and may include an electron-generating material.
For example, the organic layer may include a light emitting layer including 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 electronic device may be employed as a fluorescent host, and may also be used as fluorescent doping, and simultaneously as a fluorescent host and fluorescent doping.
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, the organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-described organic electroluminescent device compound as a main component.
In the invention, the organic electroluminescent diode device of the organic compound is characterized in that the organic electroluminescent 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, wherein the organic compound is used as a main material of the light emitting layer.
The method for preparing the organic electroluminescent device according to the present invention is not particularly limited, and may be prepared 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
The invention is further described in connection with the following embodiments in order to make the technical means, the creation features, the achievement of the purpose and the effect of the invention easy to understand.
Example 1: synthesis of Compound 5
1. Synthesis of intermediate 5-2
In a 250 ml three-neck flask was added intermediate 5-1 (11.69 g, 20 mmol), bromobenzene (3.30 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 reacted for 12 hours under the protection of nitrogen. After the 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 crude product, which was passed through a silica gel column to give compound 5-2 (8.59 g, yield 65%). LC-MS: m/600.26 (M+H) +.
2. Synthesis of Compound 5
In a 250 ml three-necked flask was charged intermediate 5-2 (13.22 g, 20 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (5.62 g, 21.0 mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-t-butylphosphine (8 mol%), potassium t-butoxide (3.8 g, 33.6 mmol) and o-xylene (80 ml). The reaction system is heated to 120 ℃ and reacted for 12 hours under the protection of nitrogen. After the 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 crude product, which was passed through a silica gel column to give compound 5 (7.14 g, yield 40%). LC-MS: M/Z891.34 (M+H) +.
Example 2: synthesis of Compound 268
Compound 268 was synthesized by the method of reference example 1, and the other steps were all referenced to the synthesis of example 1 to give compound 268 (6.69 g, yield 45%). LC-MS: M/Z742.31 (M+H) +.
Example 3: synthesis of Compound 286
Compound I-58 was synthesized by the procedure of reference example 1, and the other steps were all referenced to the synthesis of example 1 to give compound 286 (7.43 g, yield 50%). LC-MS: M/Z742.30 (M+H) +.
Example 4: synthesis of Compound 287
Compound I-85 was synthesized by the procedure of reference example 1, and the other steps were all referenced to the synthesis of example 1 to afford compound 286 (7.13 g, 48% yield). LC-MS: M/Z818.34 (M+H) +.
Example 5: synthesis of Compound 334
Compound 334 was synthesized by the method of reference example 1, and the other steps were all referenced to the synthesis of example 1, to give compound 334 (8.47 g, yield 57%). LC-MS: M/Z742.31 (M+H) +.
Example 6: synthesis of Compound 385
Compound 385 was synthesized by the method of reference example 1, and the other steps were all referred to the synthesis of example 1, to give compound 385 (7.57 g, yield 54%). LC-MS: M/Z700.26 (M+H) +.
Example 7: synthesis of Compound 386
Compound 386 was synthesized by the procedure of example 1, and the other steps were all referenced to the synthesis of example 1 to give compound 386 (8.41 g, yield 55%). LC-MS: M/Z700.25 (M+H) +.
Example 8: synthesis of Compound 387
Compound 387 was synthesized by the method of reference example 1, and the other steps were all referenced to the synthesis of example 1 to give compound 387 (17.15 g, yield 60%). LC-MS: M/Z700.24 (M+H) +.
Evaluation example 1: HOMO, LUMO, triplet level and S1-T1 level evaluation of the compound:
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the above data shows that the compound is introduced (Ar 1 Or Ar 2 ) The more the Eg (eV) value of the substance after electron withdrawing group accords with RH (phosphorescent red light main body material) condition, the delayed fluorescence performance is enhanced (S) 1 -T 1 )。
Device embodiments
(I) Evaluation of light emitting material device
The organic layer compounds used in the device examples are shown below:
1. first embodiment
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. The patterned ITO glass substrate is then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set at 1X 10-6 Torr. Thereafter on the ITO substrate with HILHI-2/>HTL-1/>Compound 5+rd-1 ((5%)>ET-1/>LiF/>And Al->Sequentially forming layers of organic material.
2. Second embodiment
An organic light-emitting device of the second embodiment was prepared 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 268 from compound 5 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the third embodiment was produced 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 286 from compound 5 of the first embodiment.
4. Fourth embodiment
An organic light-emitting device of the fourth embodiment was produced 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 287 by compound 5 of the first embodiment.
5. Fifth embodiment
An organic light-emitting device of the fifth embodiment was produced 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 the compound 334 by the compound 5 of the first embodiment.
6. Sixth embodiment
An organic light-emitting device of the fifth embodiment was produced 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 the compound 385 from the compound 5 of the first embodiment.
7. Seventh embodiment
An organic light-emitting device of the fifth embodiment was prepared by the same method as the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 386 from compound 5 of the first embodiment.
8. Eighth embodiment
An organic light-emitting device of the fifth embodiment was prepared 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 387 from compound 5 of the first embodiment.
9. Comparative example 1
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH-a by the compound 5 of the first embodiment.
10. Comparative example 2
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH-B by the compound 5 of the first embodiment.
11. Comparative example 3
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH-C by the compound 5 of the first embodiment.
12. Comparative example 4
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH-D by the compound 5 of the first embodiment.
The organic light-emitting device is manufactured at 10mA/cm 2 Voltage, efficiency and lifetime were tested under current conditions.
Table 1 shows the results of performance tests of the organic light emitting devices prepared in examples and comparative examples of the present invention.
TABLE 1
As shown in table 1, the device also operates efficiently at the same voltage. And the current efficiency and lifetime of the embodiment were significantly increased compared to the comparative example (the efficiency (16.1 cd/a) of comparative example 3 is lower than that of the similar structural example one (17.2 cd/a)).
The foregoing has outlined the basic principles, features, and advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims.
Claims (3)
1. An organic compound, wherein said organic compound is independently selected from one of the following representative compounds:
。
2. an organic electroluminescent diode device using the organic compound as claimed in claim 1, characterized in that: the organic electroluminescent device sequentially comprises a deposited anode, a hole injection layer, a hole transport layer, a luminescent 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 luminescent layer.
3. The organic electroluminescent diode 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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| KR20170026081A (en) * | 2015-08-31 | 2017-03-08 | 주식회사 엘지화학 | Compound and organic electronic device using the same |
| CN110551132A (en) * | 2018-05-31 | 2019-12-10 | 江苏三月光电科技有限公司 | ketone-containing compound and application thereof in organic electroluminescent device |
| CN111747894A (en) * | 2019-03-28 | 2020-10-09 | 江苏三月光电科技有限公司 | Compound with dibenzo-nitrogen-containing six-membered heterocyclic ring as core and application of compound in organic electroluminescent device |
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| Title |
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