CN113292560A - 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 luminous efficiency and an OLED device using the same. The structure of the organic compound provided by the invention is shown as formula 1:
in the above structural formula, Ar1And Ar2Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C6-C90 heteroarylSubstituted or unsubstituted C13-C30 amine derivatives (wherein, one must be a substituted or unsubstituted C6-C90 heteroaryl group containing two or more nitrogen atoms, a heterocyclic group, or a substituted or unsubstituted C13-C30 amine derivative); r1And R2Is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C3-C30 heteroaryl, R1And R2The rings 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 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 a positive electrode and a negative electrode and then migrate, recombine and attenuate in an organic material to generate light. 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 efficient electron transport, the design and synthesis of new hole blocking materials, 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 to prevent the energy reverse transfer of exciton transition release. Currently, materials having both a high triplet level and good hole mobility in the host material are still lacking. Therefore, how to design a new host material with better performance is 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 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, Ar1And Ar2Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 fused ring, substituted or unsubstituted C6-C90 heteroaryl, substituted or unsubstituted C13-C30 amine derivatives (wherein, one must be substituted or unsubstituted C6-C90 heteroaryl containing two or more nitrogen atoms, heterocyclic group, or substituted or unsubstituted C13-C30 amine derivative);
R1and R2Is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 condensed ring group, substituted or unsubstituted C3-C30 heteroaryl, R1And R2The rings may be linked to form a ring.
Further preferably, Ar in the structure of the organic compound is Ar1And Ar2Independently selected from the following structures, but not represented as being limited thereto:
wherein R is3、R4And R5Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a combination thereof;
X1、X2、X3independently selected from nitrogen (N) or carbon (C);
L1is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 condensed ring group, substituted or unsubstituted C3-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 is3、R4And R5Independently selected from one or more of the following structures, but not represented as being limited thereto:
wherein R is8、R9、R10Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or the combination thereof;
L2is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, and substituted or unsubstituted C3-C30 heteroaryl.
In a further preferred manner, said organic compounds are independently selected from the following compounds, but not representing a limitation thereto:
the invention also provides application of the fluorene 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 fluorene series.
The invention has the beneficial effects that:
the invention provides a fluorene series-containing compound, which has a structure shown in a formula 1, wherein an electron-rich structure in the fluorene series compound has great influence on the photoelectric property of the whole compound molecule, so that unnecessary vibration energy loss is reduced, and high-efficiency luminescence performance is realized. By adjusting substituent groups, the compound has better thermal stability and chemical properties. The fluorene series-containing compound disclosed by the invention is simple in preparation method, easy in raw material obtaining and capable of meeting the industrial requirements.
The fluorene 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 technical 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 technical layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties may be formed using a conventional hole injection material, a hole transport material, or a material having both hole injection and hole transport properties, and may further include an 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, as a fluorescent dopant, and as both a fluorescent host and a fluorescent dopant.
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 method for preparing the organic electroluminescent device is not particularly limited, and the organic electroluminescent device can be prepared by using the method and materials for preparing the 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 characteristics, the achievement purposes and the effects of the invention easy to understand, the invention is further described with the specific embodiments.
Example 1: synthesis of Compound 5
1. Synthesis of intermediate 5-2
In a 250 ml three-necked flask were 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 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 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 were added 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-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 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 carried out by the synthesis of reference 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 according to the procedure of example 1, and the other steps were carried out according to the synthesis of example 1, to obtain 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 according to the procedure of example 1, and the other procedures were carried out according to the synthesis of example 1, to obtain compound 286(7.13 g, yield 48%). 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 carried out by the synthesis of reference example 1 to obtain 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 synthesis of example 1 was referenced for the other steps to obtain 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 method of example 1 and the other steps were carried out by the synthesis of example 1 to obtain compound 386(8.41 g, 55% yield). LC-MS: M/Z700.25(M + H) +.
Example 8: synthesis of Compound 387
Compound 387 was synthesized according to the procedure described in example 1, and the other steps were carried out according to the synthesis of example 1 to obtain compound 387(17.15 g, yield 60%). LC-MS: M/Z700.24(M + H) +.
Evaluation example 1: HOMO, LUMO, triplet energy level, and S1-T1 energy level evaluation of the compounds:
the above data show that introduction (Ar) into the compound1Or Ar2) The more the Eg (eV) value of the substance after the electron withdrawing group meets the RH (phosphorescent red light main body material) condition, the delayed fluorescence property (S) is enhanced1-T1)。
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 3mm × 3 mm. The patterned ITO glass substrate was then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set at 1X 10-6 Torr. Thereafter, HIL was applied to the ITO substrate
HI-2
HTL-1
Compound 5+ RD-1 ((5%)
ET-1
LiF
And Al
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 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 instead of compound 5 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 286 from compound 5 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 287 from compound 5 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 334 instead of compound 5 of the first embodiment.
6. Sixth 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 385 from compound 5 of the first embodiment.
7. Seventh 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 386 from compound 5 of the first embodiment.
8. Eighth 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 387 instead of compound 5 of the first embodiment.
9. Comparative example 1
An organic light-emitting device of comparative example was prepared 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-a from the compound 5 of the first embodiment.
10. Comparative example 2
An organic light-emitting device of comparative example was prepared 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-B from the compound 5 of the first embodiment.
11. Comparative example 3
An organic light-emitting device of comparative example was prepared 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-C from the compound 5 of the first embodiment.
12. Comparative example 4
An organic light-emitting device of comparative example was prepared 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-D from the compound 5 of the first embodiment.
The prepared organic light-emitting device is at 10mA/cm2Voltage, 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.
TABLE 1
As shown in table 1, the device also operated efficiently at the same voltage. And the current efficiency and lifetime of the embodiment were significantly increased compared to the comparative example (the efficiency of comparative example 3 (16.1cd/a) was lower than that of example one (17.2cd/a) of the similar structure).
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 (10)
1. An organic compound having a formula shown in formula 1:
wherein Ar is1And Ar2Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 fused ring, substituted or unsubstituted C6-C90 heteroaryl, substituted or unsubstituted C13-C30 amine derivatives (wherein, one must be substituted or unsubstituted C6-C90 heteroaryl containing two or more nitrogen atoms, heterocyclic group, or substituted or unsubstituted C13-C30 amine derivative);
R1and R2Is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 condensed ring group, substituted or unsubstituted C3-C30 heteroaryl, R1And R2The rings may be linked to form a ring.
2. An organic compound according to claim 1, wherein Ar is1And Ar2Independently selected from one of the following representative structures:
wherein R is3、R4And R5Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a combination thereof;
X1、X2、X3independently selected from nitrogen (N) or carbon (C);
L1is a single bond or is selected from substitutedOr unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 fused ring group, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
3. An organic compound according to claim 1 or 2, wherein R is3、R4And R5Independently selected from one or more of the following representative groups:
wherein R is8、R9、R10Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a combination thereof;
L2is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 condensed ring group, and substituted or unsubstituted C3-C30 heteroaryl.
4. The organic compound according to any one of claims 1 or 2, wherein the organic compound is independently selected from one of the following representative compounds:
5. an organic electroluminescent diode device using the organic compound according to any one of claims 1 to 4, 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 material of the luminescent layer.
6. The organic electroluminescent diode device according to claim 5, wherein the compound according to any one of claims 1 to 4 can be used alone or in combination with other compounds.
7. The organic electroluminescent diode device according to claim 5 or 6, wherein the organic compound according to any one of claims 1 to 4 serves as an electron blocking layer.
8. The organic electroluminescent diode device according to claim 5 or 6, wherein the organic compound according to any one of claims 1 to 4 is used as a light-emitting layer.
9. The organic electroluminescent diode device according to claim 5 or 6, wherein the organic compound according to any one of claims 1 to 4 is used as a hole blocking layer.
10. The organic electroluminescent diode device according to claim 5 or 6, wherein the organic compound according to any one of claims 1 to 4 is used as an electron transport layer.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2021
- 2021-04-30 CN CN202110481193.7A patent/CN113292560B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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