KR-102963372-B1 - Organic light emitting device

Abstract

The present invention provides an organic light-emitting diode.

Inventors

• 이길선
• 이재철
• 김용욱
• 김신성
• 백이현
• 함경록
• 조범신

Assignees

• 주식회사 엘지화학

Dates

Publication Date

20260508

Application Date

20200828

Claims (12)

1. It includes an anode; a cathode; and a light-emitting layer between the anode and the cathode, The light-emitting layer comprises a compound represented by the following chemical formula 1-1 and a compound represented by the following chemical formula 5, Organic light-emitting diode: [Chemical Formula 1-1] In the above chemical formula 1-1, Ar 1 and Ar 2 are each independently a C 6-60 aryl; or a C 2-60 heteroaryl comprising one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S, and Ar 3 and Ar 4 are each independently selected from the group consisting of the following, and In the above, R1 and R2 are each independently methyl or phenyl, and [Chemical Formula 5] In the above chemical formula 5, Ar 11 is a C 6-60 aryl substituted with one or more deuterium; or a C 2-60 heteroaryl comprising one or more heteroatoms selected from the group consisting of N, O, and S substituted with one or more deuterium, and Ar 12 is a C 6-60 aryl substituted with one or more deuterium; or a C 2-60 heteroaryl comprising one or more heteroatoms selected from the group consisting of N, O, and S substituted with one or more deuterium, and R 11 is deuterium, and z is an integer from 0 to 8.
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3. In paragraph 1, Ar 1 and Ar 2 are each independently selected from any one of the group consisting of the following, Organic light-emitting diode: As mentioned above, X 1 to X 5 are each independently CR' 1 or N, and R'1 is each independently a C2-20 heteroaryl comprising one or more heteroatoms selected from the group consisting of hydrogen; halogen; C1-10 alkyl; C1-10 alkoxy; C6-20 aryloxy; C1-10 alkylamino; C6-20 arylamino; C1-10 alkylsilyl ; C6-20 arylsilyl; C6-20 aryl; or N, O, and S, and m is an integer from 0 to 7, each independently, and X 6 is NR' 2 , C(R' 2- ) 2 , O, or S, and R' 2 is each independently a C 2-20 heteroaryl comprising one or more heteroatoms selected from the group consisting of hydrogen; C 1-10 alkyl; C 6-20 aryl; or N, O and S.
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9. In paragraph 1, The compound represented by chemical formula 1-1 is any one selected from the group consisting of the following, Organic light-emitting diode: .
10. In paragraph 1, Ar 11 is naphthyl substituted with one or more deuterium atoms, or naphthylphenyl substituted with one or more deuterium atoms, Organic light-emitting diode.
11. In paragraph 1, Ar 12 is naphthylphenyl substituted with one or more deuterium atoms, or dibenzofuranyl substituted with one or more deuterium atoms, Organic light-emitting diode.
12. In paragraph 1, The above chemical formula 5 is represented by any one of the following chemical formulas 5-1 to 5-4, Organic light-emitting diode: [Chemical Formula 5-1] In the above chemical formula 5-1, o+p+q+r is an integer from 21 to 23, and [Chemical Formula 5-2] In the above chemical formula 5-2, o+p+q+r is an integer from 21 to 23, and [Chemical Formula 5-3] In the above chemical formula 5-3, s+p+r is an integer from 21 to 22, and [Chemical Formula 5-4] In the above chemical formula 5-4, s+p+q+r is an integer from 23 to 24.

Description

Organic light emitting device The present invention relates to an organic light-emitting diode. Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) utilizing this phenomenon possess wide viewing angles, excellent contrast, and fast response times, and are being extensively researched due to their superior characteristics in terms of brightness, driving voltage, and response speed. Organic light-emitting diodes generally have a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. To increase the efficiency and stability of the organic light-emitting diode, the organic layer is often composed of a multilayer structure made of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting diode, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton falls back to the ground state. There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices as described above. Meanwhile, recently, organic light-emitting diodes (OLEDs) are being developed using solution processes, particularly inkjet processes, instead of conventional deposition processes to reduce process costs. In the early stages, there were attempts to develop OLEDs by coating all OLED layers using a solution process, but due to limitations in current technology, research is underway on a hybrid process in which only HIL, HTL, and EML are processed using a solution process, while subsequent processes utilize conventional deposition processes. Accordingly, the present invention provides a novel organic light-emitting diode material that can be used in organic light-emitting diodes and simultaneously in solution processes, and an organic light-emitting diode using the same. FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron transport layer (7), an electron injection layer (8), and a cathode (4). The present invention will be described in more detail below to aid in understanding. (Definition of Terms) In this specification, and means a bond connected to another substituent. In this specification, the term “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thioxy group; aryl thioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heteroaryl comprising one or more atoms of N, O, and S, or substituted or unsubstituted with two or more of the exemplified substituents connected. For example, “substituents connected with two or more substituents” may be a biphenyl group. That is, the biphenyl group can be an aryl group, or it can be interpreted as a substituent in which two phenyl groups are connected. In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto. In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto. In the present specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto. In this specification, the silyl groups specifically include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.