CN113248489A - Organic compound and organic light-emitting device using same - Google Patents

Organic compound and organic light-emitting device using same Download PDF

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CN113248489A
CN113248489A CN202110372634.XA CN202110372634A CN113248489A CN 113248489 A CN113248489 A CN 113248489A CN 202110372634 A CN202110372634 A CN 202110372634A CN 113248489 A CN113248489 A CN 113248489A
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substituted
unsubstituted
heteroaryl
organic
emitting device
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高春吉
王子兴
张迪
陈清泉
吕伯彦
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Zhejiang Huadisplay Optoelectronics Co Ltd
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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:
Figure DDA0003009937310000011
in the above structural formula, R1And R2One of which is an optionally substituted C4-C90 heteroaryl group, a nitrogen (N) -containing heteroA cyclic or amine series of groups, the other being a substituted or unsubstituted C6-C90 heteroaryl or heterocyclic group containing more than two nitrogen atoms; x1、X2Independently selected from the group consisting of a single bond, sulfur (S), Sulfur Oxide (SO), or sulfur dioxide (SO)2) And at least one is not a single bond.

Description

Organic compound and organic light-emitting device using same
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,
Figure BDA0003009937300000021
in the above structural formula, R1And R2One is an optionally substituted C4-C90 heteroaryl group, a heterocyclic group containing nitrogen (N), or an amine series group, and the other is a substituted or unsubstituted C6-C90 heteroaryl or heterocyclic group containing two or more nitrogen atoms;
X1、X2independently selected from the group consisting of a single bond, sulfur (S), Sulfur Oxide (SO), or sulfur dioxide (SO)2) And at least one is not a single bond.
Preferably, an organic compound characterized by: the structural formula is shown as 1-2:
Figure BDA0003009937300000022
wherein R is1And R2One is an optionally substituted C4-C90 heteroaryl group, a heterocyclic group containing nitrogen (N), or an amine series group, and the other is a substituted or unsubstituted C6-C90 heteroaryl or heterocyclic group containing two or more nitrogen atoms;
R3and R4Each independently 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;
l is a single bond or 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;
X1、X2independently selected from the group consisting of a single bond, sulfur (S), Sulfur Oxide (SO), or sulfur dioxide (SO)2) And at least one is not a single bond.
In a further preferred embodiment, R in the structure of the organic compound is1And R2Independently selected from the following structures:
Figure BDA0003009937300000031
wherein R is5、R6And R7Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-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 C10-C30 condensed 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 is3And R4Independently selected from the following structures:
Figure BDA0003009937300000041
Figure BDA0003009937300000051
Figure BDA0003009937300000061
wherein R is8、R9、R10Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-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 C4-C30 heteroaryl.
In a further preferred manner, the organic compounds are independently selected from the following compounds:
Figure BDA0003009937300000071
Figure BDA0003009937300000081
Figure BDA0003009937300000091
Figure BDA0003009937300000101
Figure BDA0003009937300000111
Figure BDA0003009937300000121
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 heterocyclic series-containing compound disclosed by the invention is simple in preparation method, easily available in raw materials and capable of meeting the industrial requirements.
The heterocyclic series compounds are prepared into devices, particularly used as main materials, the devices have the advantages of low driving voltage and high light-emitting 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, 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 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 Compounds 2-6
1. Synthesis of intermediate 2-6-2
Figure BDA0003009937300000141
To a 500 ml reaction flask were added the intermediate phenothiazineboronic acid ester (19.97 g, 61.4 mmol), 2-6-1(30.05 g, 61.4 mmol), tetrakis (triphenylphosphine) palladium (5 mol%), potassium carbonate (17.0 g, 122.8 mmol), 1, 4-dioxane (200 ml) and water (50 ml). The reaction system is heated to 80 ℃ 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,The crude product obtained by recrystallization was passed through a silica gel column to obtain intermediate 2-6-2(26.12 g, yield 70%). LC-MS: M/Z607.21 (M + H)+。
2. Synthesis of Compounds 2-6
Figure BDA0003009937300000142
In a 250 ml three-necked flask were charged the intermediates 2-6-2(12.16 g, 20 mmol), 2-bromo-3-phenylquinoxaline (5.99 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 2-6(10.56 g, yield 65%). LC-MS: M/Z838.29(M + H)+。
Example 2: synthesis of Compound 3-2
Compound 3-2 was synthesized by the method of reference example 1 to give compound 3-2(11.22 g, yield 78%). LC-MS: M/Z838.29(M + H)+。
Example 3: synthesis of Compounds 3 to 8
Compounds 2 to 6 were synthesized by the method of reference example 1 to give compounds 3 to 8(14.79 g, yield 87%). LC-MS: M/Z914.32(M + H)+。
Example 4: synthesis of Compounds 3-9
Compound 3-9 was synthesized by the method of reference example 1 to give compound 3-9(14.65 g, yield 80%). LC-MS: M/Z836.27(M + H)+。
Example 5: synthesis of Compounds 3-17
Compounds 3 to 17 were synthesized by the method of reference example 1 to give compounds 3 to 17(10.36 g, yield 70%). LC-MS: M/Z888.30(M + H)+。
Example 6: synthesis of Compound 4-1
1. Synthesis of intermediate 2-1
Compound 2-1 was synthesized by the method of reference example 1 to give compound 2-1(10.15 g, yield 80%). LC-MS: M/Z811.28(M + H)+。
2. Synthesis of Compound 4-1
Figure BDA0003009937300000151
In a 250 ml three-necked flask, 2-1(16.24 g, 20 mmol), dichloromethane (200 ml), m-chloroperoxybenzoic acid (12.08 g, 70 mmol) were added. The reaction system is heated to 40 ℃ and reacts for 3 hours under stirring. 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 4-1(14.35 g, yield 85%). LC-MS: M/Z843.27 (M + H)+. Evaluation example 1: HOMO, LUMO, triplet energy level, and S1-T1 energy level evaluation of the compounds:
Figure BDA0003009937300000152
Figure BDA0003009937300000161
the above data show that the HOMO and eg (eV) values of the substances are reduced after the amine-series compound is introduced into the compound, and the delayed fluorescence property (S) is exhibited after the amine-series compound is introduced into the compound1-T1) And (5) reinforcing.
Device embodiments
(I) Evaluation of luminescent Material devices
The compounds of the respective organic layers used in the device examples are as follows:
Figure BDA0003009937300000171
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 10-6And (4) supporting. Thereafter, HIL was applied to the ITO substrate
Figure BDA0003009937300000172
HI-2
Figure BDA0003009937300000173
HTL-1
Figure BDA0003009937300000174
Compound 2-6+ RD-1 ((5%)
Figure BDA0003009937300000175
ET-1
Figure BDA0003009937300000176
LiF
Figure BDA0003009937300000177
And Al
Figure BDA0003009937300000178
The sequence of (a) and (b) forming layers of organic material.
2. Second 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 3-2 instead of compound 2-6 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the fifth 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 compounds 3 to 8 from compounds 2 to 6 of the first embodiment.
4. Fourth 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 compounds 3 to 9 from compounds 2 to 6 of the first embodiment.
5. Fifth 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 compounds 3 to 17 from compounds 2 to 6 of the first embodiment.
6. Sixth embodiment
An organic light-emitting device of a 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 4-1 instead of compound 2-6 of the first embodiment.
7. Comparative example 1
An organic light-emitting device of comparative example 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 the compound RH-B from the compounds 1 to 38 of the first embodiment.
8. Comparative example 2
An organic light-emitting device of comparative example 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 the compound RH-C from the compounds 1 to 38 of the first embodiment.
9. Comparative example 3
An organic light-emitting device of comparative example 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 the compound RH-D from the compounds 1 to 38 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.
Figure BDA0003009937300000181
As shown in table 1, the device also operated efficiently at the same voltage. And the current efficiency and the life of the embodiment are significantly increased as compared to the comparative example.
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 characterized by: the structural formula is shown as 1:
Figure FDA0003009937290000011
in the above structural formula, R1And R2One is an optionally substituted C4-C90 heteroaryl group, a heterocyclic group containing nitrogen (N), or an amine series group, and the other is a substituted or unsubstituted C6-C90 heteroaryl or heterocyclic group containing two or more nitrogen atoms;
X1、X2independently selected from the group consisting of a single bond, sulfur (S), Sulfur Oxide (SO), or sulfur dioxide (SO)2) And at least one is not a single bond.
2. An organic compound characterized by: the structural formula is shown as 1-2:
Figure FDA0003009937290000012
wherein R is1And R2One is an optionally substituted C4-C90 heteroaryl group, a heterocyclic group containing nitrogen (N), or an amine series group, and the other is a substituted or unsubstituted C6-C90 heteroaryl or heterocyclic group containing two or more nitrogen atoms;
R3and R4Each independently selected from substituted or unsubstitutedSubstituted 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;
l is a single bond or 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;
X1、X2independently selected from the group consisting of a single bond, sulfur (S), Sulfur Oxide (SO), or sulfur dioxide (SO)2) And at least one is not a single bond.
3. An organic compound according to claim 1, wherein R is1And R2Independently selected from the following:
Figure FDA0003009937290000021
wherein R is5、R6And R7Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-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 C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
4. An organic compound according to claim 2, wherein R is3And R4Independently selected from the following compounds:
Figure FDA0003009937290000031
Figure FDA0003009937290000041
wherein R is8、R9、R10Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-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 C4-C30 heteroaryl.
5. The organic compound according to any one of claims 1 to 4, wherein: the organic compound is independently selected from one of the following compounds:
Figure FDA0003009937290000051
Figure FDA0003009937290000061
Figure FDA0003009937290000071
Figure FDA0003009937290000081
Figure FDA0003009937290000091
Figure FDA0003009937290000101
6. an organic light-emitting device using the organic compound according to any one of claims 1 to 5, 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.
7. The organic light-emitting device according to claim 6, wherein the compound according to any one of claims 1 to 5 is used alone or in combination with other compounds.
8. An organic light-emitting device according to claim 6, wherein the compound according to any one of claims 1 to 5 is used as a light-emitting layer or an active layer.
9. An organic light-emitting device according to claim 6, wherein the compound according to any one of claims 1 to 5 is used as a hole-blocking layer.
10. An organic light-emitting device according to claim 6, wherein the compound according to any one of claims 1 to 5 is used as an electron-transporting layer.
CN202110372634.XA 2021-04-07 2021-04-07 Organic compound and organic light-emitting device using same Pending CN113248489A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160028025A1 (en) * 2013-03-18 2016-01-28 Idemitsu Kosan Co., Ltd. Light-emitting device
WO2018080067A1 (en) * 2016-10-27 2018-05-03 주식회사 두산 Organic compound and organic electroluminescent device including same
WO2019120099A1 (en) * 2017-12-21 2019-06-27 广州华睿光电材料有限公司 Organic mixture and use thereof in organic electronic device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160028025A1 (en) * 2013-03-18 2016-01-28 Idemitsu Kosan Co., Ltd. Light-emitting device
WO2018080067A1 (en) * 2016-10-27 2018-05-03 주식회사 두산 Organic compound and organic electroluminescent device including same
WO2019120099A1 (en) * 2017-12-21 2019-06-27 广州华睿光电材料有限公司 Organic mixture and use thereof in organic electronic device

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