KR-102963245-B1 - An electroluminescent compound and an electroluminescent device comprising the same

KR102963245B1KR 102963245 B1KR102963245 B1KR 102963245B1KR-102963245-B1

Abstract

The present invention relates to a novel organic light-emitting compound represented by [Chemical Formula I] that can be employed in an organic layer, such as an electron transport layer, within an organic light-emitting device to realize light-emitting characteristics such as low voltage driving of the device and excellent light-emitting efficiency, and to an organic light-emitting device including the same. [Chemical Formula I]

Inventors

윤석근
현서용

Assignees

(주)피엔에이치테크

Dates

Publication Date: 20260511
Application Date: 20210401

Claims (7)

Organic light-emitting compounds represented by the following [Chemical Formula I]: [Chemical Formula I] In the above [Chemical Formula I], X is O, S, or NR 1 , and The above R1 is any one selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, and substituted or unsubstituted C3 to C30 heteroaryl group. L is a single bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms (excluding carbazoylene groups), and m is an integer from 0 to 3, and if m is 2 or greater, multiple Ls are identical or different from each other, A is represented by the following [Structural Formula 1] or [Structural Formula 2], and [Structural Formula 1] [Structural Formula 2] In the above [Structural Formula 1] and [Structural Formula 2], X 1 to X 3 are identical or different from each other, and each is independently CH or N, and L1 is a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms (excluding carbazoylene groups), and o is an integer from 0 to 3, and if o is 2 or more, multiple L 1s are identical or different from each other, Ar 1 and Ar 2 are identical or different from each other and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms (excluding carbazole groups), and However, if all of the above X1 to X3 are CH, at least one of the above Ar1 and Ar2 is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms (except for carbazole groups), characterized in that q and r are integers from 1 to 3, and when q and r are each 2 or more, the plurality of Ar 1 and Ar 2 are each identical or different from each other, and Ar 3 is any one selected from substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms (excluding thiophenyl, furanyl, pyrrole, imidazoleyl, and carbazoleyl groups), and p is an integer from 1 to 3, and if p is 2 or more, the plurality of Ar 3 are identical or different from each other, and n is an integer from 1 to 3, and when n is 2 or greater, the structures within the plurality of parentheses [ ] are identical or different from each other, and l is an integer from 1 to 2, and when l is 2, each A is the same or different from each other, and In the definitions of R1 , L, L1 and Ar1 to Ar3 above, "substituted or unsubstituted" means that R1 , L, L1 and Ar1 to Ar3 are each substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, silyl group, alkyl group, halogenated alkyl group, deuteriumated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuteriumated alkoxy group, aryl group, and heteroaryl group (excluding carbazole group), are substituted with a substituent in which two or more of the said substituents are connected, or have no substituents.
In paragraph 1, The above [Chemical Formula I] is an organic light-emitting compound selected from any one of the following [Chemical Formula I-1] to [Chemical Formula I-4]: [Chemical Formula I-1] [Chemical Formula I-2] [Chemical Formula I-3] [Chemical Formula I-4] In the above [Chemical Formula I-1] to [Chemical Formula I-4], the definitions of X, L, A, n, and m are the same as the definitions in the above [Chemical Formula I].
delete
In paragraph 1, An organic light-emitting compound characterized in that the above [Chemical Formula I] is any one selected from the following compounds:
An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, An organic light-emitting device in which at least one of the above organic layers comprises an organic light-emitting compound of [Chemical Formula I] according to claim 1.
In paragraph 5, The above organic layer comprises one or more layers selected from a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport functions simultaneously, an electron transport layer, an electron injection layer, a layer that performs electron transport and electron injection functions simultaneously, an electron blocking layer, a hole blocking layer, and a light-emitting layer. An organic light-emitting device characterized in that at least one of the above layers comprises an organic light-emitting compound represented by [Chemical Formula I].
In paragraph 6, An organic light-emitting device characterized by including an organic light-emitting compound represented by [Chemical Formula I] in any one of the electron transport layer, the electron injection layer, and the layer that simultaneously performs electron transport and electron injection functions.

Description

An electroluminescent compound and an electroluminescent device comprising the same The present invention relates to an organic light-emitting compound, and more specifically, to an organic light-emitting compound characterized by being employed as an organic layer material within an organic light-emitting device, and to an organic light-emitting device in which the light-emitting characteristics, such as low-voltage operation of the device and excellent light-emitting efficiency, are significantly improved by employing the same. Organic light-emitting diodes (OLEDs) can be formed on transparent substrates, and compared to plasma display panels or inorganic light-emitting diode (EL) displays, they have the advantages of being able to operate at a low voltage of 10 V or less, consuming relatively little power, and having excellent color quality, and can display three colors of green, blue, and red, so they have recently become the subject of much interest as next-generation display devices. However, for such organic light-emitting diodes to exhibit the characteristics described above, it is necessary for the materials forming the organic layer within the device—such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials—to be supported by stable and efficient materials; yet, the development of stable and efficient organic layer materials for organic light-emitting diodes has not yet been sufficiently achieved. Therefore, in order to realize more stable organic light-emitting diodes and to achieve high efficiency, long lifespan, and large scale, further improvements in efficiency and lifespan characteristics are required; in particular, there is an urgent need for the development of materials constituting each organic layer of the organic light-emitting diode. The present invention will be described in more detail below. The present invention relates to an organic light-emitting compound represented by the following [Chemical Formula I], which can achieve light-emitting characteristics such as low-voltage driving of an organic light-emitting device and excellent light-emitting efficiency. The structure is characterized by a skeletal structure represented by [Chemical Formula I] below, that is, by introducing a characteristic substituent A through a linker (L) into one or more oxazoloquinoline, thiazoloquinoline, and mimidazoquinoline derivatives, and through this structural feature, the low-voltage driving characteristics and luminous efficiency characteristics of the organic light-emitting diode can be improved. [Chemical Formula I] In the above [Chemical Formula I], X is O, S, or NR 1 , and R 1 is selected from hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C3 to C20 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group and substituted or unsubstituted C3 to C30 heteroaryl group. L is a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and m is an integer from 0 to 3, and if m is 2 or more, a plurality of Ls are identical or different from each other. A is characterized by being represented by the following [Structural Formula 1] or [Structural Formula 2]. [Structural Formula 1] [Structural Formula 2] In the above [Structural Formula 1] and [Structural Formula 2], X 1 to X 3 are identical or different from each other, and each is independently CH or N. L1 is a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and o is an integer from 0 to 3, and when o is 2 or more, a plurality of L1s are identical or different from each other. Ar 1 and Ar 2 are identical or different from each other and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, q and r are integers from 0 to 3, and when q and r are each 2 or more, the plurality of Ar 1 and Ar 2 are each identical or different from each other. Ar 3 is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, p is an integer from 0 to 3, and when p is 2 or more, the plurality of Ar 3 are identical or different from each other. n is an integer from 1 to 3, and when n is 2 or greater, the structures inside the plurality of parentheses [ ] are identical or different from each other. l is an integer from 1 to 2, and when l is 2, each A is the same or different from each other. According to one embodiment of the present invention, [Chemical Formula I] may be any one