Search

KR-20260067897-A - ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

KR20260067897AKR 20260067897 AKR20260067897 AKR 20260067897AKR-20260067897-A

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device containing the same, and more specifically, to an organic compound having excellent characteristics such as electron injection and transport capacity, luminescence capacity, electrochemical stability, and thermal stability, and an organic electroluminescent device having improved characteristics such as luminescence efficiency, driving voltage, and lifespan by including the same in one or more organic layers.

Inventors

  • 신성민
  • 심재의
  • 조석원

Assignees

  • 솔루스첨단소재 주식회사

Dates

Publication Date
20260513
Application Date
20241106

Claims (9)

  1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 to X 3 are identical or different from each other, and each is independently N or CR', provided that at least one of X 1 to X 3 is N, R' is selected from the group consisting of hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 – C40 alkyl group, C2 – C40 alkenyl group, C2 – C40 alkynyl group, C3 – C40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6 – C60 aryl group, and heteroaryl group having 5 to 60 nuclei, and Ar 1 and Ar 2 are identical or different from each other, and each independently a C 1 –C 40 alkyl group, a C 2 –C 40 alkenyl group, a C 2 –C 40 alkynyl group, a C 3 –C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclei, a C 6 –C 60 aryl group, a heteroaryl group having 5 to 60 nuclei, a C 1 –C 40 alkyloxy group, a C 6 –C 60 aryloxy group, a C 3 –C 40 alkylsilyl group, a C 6 –C 60 arylsilyl group, a C 1 –C 40 alkylboron group, a C 6 –C 60 arylboron group, a C 6 –C 60 arylphosphine group, and a C 6 –C Selected from the group consisting of 60 arylphosphine oxide groups, C6 – C60 arylamine groups, C5 – C60 arylheteroarylamine groups, and heteroarylamine groups having 5 to 60 nuclei, L1 is a single bond or is selected from the group consisting of a C5 – C60 arylene group and a heteroarylene group having 5 to 40 nuclei, and A is represented by the following chemical formula 2, and [Chemical Formula 2] In the above chemical formula 2 R1 to R3 are identical or different from one another and each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1 – C40 alkyl group, C2 – C40 alkenyl group, C2 – C40 alkynyl group, C3 – C40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6 – C60 aryl group, heteroaryl group having 5 to 60 nuclei, C1– C40 alkyloxy group, C6 –C60 aryloxy group, C3 – C40 alkylsilyl group, C6 – C60 arylsilyl group, C1 – C40 alkylboron group , C6 – C60 arylboron group, C Selected from the group consisting of a 6 - C60 arylphosphine group, a C6 - C60 arylphosphine oxide group, a C6 - C60 arylamine group, a C5 - C60 arylheteroarylamine group, and a heteroarylamine group having 5 to 60 nuclei, n is an integer from 0 to 2, and m and o are each independently integers from 0 to 3, and Any one of * refers to a region connected to L1 of the above chemical formula 1, and Ar3 is a C1 – C40 alkyl group, a C2 – C40 alkenyl group, a C2 – C40 alkynyl group, a C3 – C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclei, a C6 – C60 aryl group, a heteroaryl group having 5 to 60 nuclei, a C1 – C40 alkyloxy group, a C6 –C60 aryloxy group, a C3 – C40 alkylsilyl group, a C6 –C60 arylsilyl group, a C1 – C40 alkylboron group, a C6 – C60 arylboron group, a C6 – C60 arylphosphine group, a C6 – C60 arylphosphine oxide group, C6 It is selected from the group consisting of ~C 60 arylamine groups, C 5 ~C 60 arylheteroarylamine groups and heteroarylamine groups having 5 to 60 nuclei. The arylene group, heteroarylene group of L1 , the alkyl group, alkenyl group , alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, arylheteroarylamine group, and heteroarylamine group are each independently deuterium (D), halogen, cyano group, nitro group, C1 - C40 alkyl group, C2 - C40 alkenyl group, C2 - C40 alkynyl group, C3 - C40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, It may be substituted with one or more substituents selected from the group consisting of a C6 – C60 aryl group, a heteroaryl group having 5 to 60 nuclei, a C1 – C40 alkyloxy group, a C6 – C60 aryloxy group, a C1 – C40 alkylsilyl group, a C6 – C60 arylsilyl group, a C1 – C40 alkylboron group, a C6 – C60 arylboron group, a C6 – C60 arylphosphine group, a C6 – C60 arylphosphine oxide group, a C6– C60 arylamine group, a C5 –C60 arylheteroarylamine group, and a heteroarylamine group having 5 to 60 nuclei; wherein, if there are multiple substituents, they may be identical or different from each other. They exist and can combine or condense with each other to form a condensation ring.
  2. In paragraph 1, The above-mentioned Ar 1 and Ar 2 are identical or different from each other, and each is independently selected from any one of the following structural formulas, a compound:
  3. In paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 3 to 23: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] In the above chemical formulas 3 to 23, Ar 1 ~ Ar 3 , L 1 , R 1 ~ R 3 , m, n and o are defined in chemical formulas 1 and 2, respectively.
  4. In paragraph 1, A compound represented by the above chemical formula 2 is represented by any one of the following chemical formulas 24 to 29: [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] In the above chemical formulas 24 to 29, Ar 3 , R 1 ~ R 3 , n, m, and o are each defined in Chemical Formula 2.
  5. In paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 30 to 38: [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 36] [Chemical Formula 37] [Chemical Formula 38] In the above chemical formulas 30 to 38, X 1 ~ X 3 , Ar 1 ~ Ar 3 , R 1 ~ R 3 , m, n and o are defined in chemical formulas 1 and 2, respectively.
  6. In paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 39 to 77: [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50] [Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53] [Chemical Formula 54] [Chemical Formula 55] [Chemical Formula 56] [Chemical Formula 57] [Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62] [Chemical Formula 63] [Chemical Formula 64] [Chemical Formula 65] [Chemical Formula 66] [Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69] [Chemical Formula 70] [Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74] [Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]
  7. In paragraph 1, Compound represented by the above chemical formula 1 is selected from the group consisting of the following compounds 1 to 384:
  8. Anode; cathode; and one or more organic layers interposed between the anode and the cathode, comprising An organic electroluminescent device comprising at least one of the above one or more organic layers, wherein the organic compound described in any one of claims 1 to 7.
  9. In paragraph 8, An organic electroluminescent device in which the organic layer containing the above organic compound is an electron transport layer or an electron transport auxiliary layer.

Description

Organic compound and organic electroluminescent device comprising the same The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to a novel compound and an organic electroluminescent device in which characteristics such as luminous efficiency, driving voltage, and lifespan are improved by including the same in one or more organic layers. In an organic electroluminescent device, when a voltage is applied between 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, excitons are formed, and light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host/dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer. Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials. To date, NPB, BCP, and Alq 3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy) 3 , and (acac)Ir(btp) 2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material. However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required. The present invention will be described in detail below. <New Organic Compounds> The present invention provides a novel compound that exhibits excellent electron transport capacity, luminescence capacity, and thermal stability, thereby enabling the device to display low voltage, high luminescence efficiency, and long lifespan characteristics. According to the present invention, a compound represented by the following chemical formula 1 has a basic skeletal structure centered on a nitrogen-containing heteroaromatic ring (e.g., azine, X1 to X3 containing ring) having an electron withdrawing group (EWG), wherein a quinoxalinophenoxazine-based moiety (e.g., R1 to R3 containing moiety) represented by the following chemical formula 2 is directly connected or connected through a separate linker (e.g., L1 ). [Chemical Formula 1] [Chemical Formula 2] Specifically, the compound of Chemical Formula 1 contains a nitrogen-containing heteroaromatic ring (e.g., an azine moiety) with EWG characteristics in its molecular skeletal structure, and a moiety unit of Chemical Formula 2 (quinozalinophenoxazine moiety) is introduced on one side of the nitrogen-containing heteroaromatic ring. Here, the nitrogen-containing heteroaromatic ring is used as an electron acceptor to control the LUMO value suitable for the electron transport layer or electron transport auxiliary layer, and plays a role in enabling electrons to be smoothly transferred to the light-emitting layer, thereby improving the efficiency and lifespan characteristics of the device. In addition, when fabricating a device using the compound of Chemical Formula 1 above, the quinozalinophenoxazine moiety of each compound acts as an EDG, which can effectively accept electrons from the cathode and smoothly transfer electrons to the light-emitting layer, thereby affecting the transfer speed and simultaneously minimizing damage that may occur due to excess holes that are not used in the light-emitting layer, thereby lowering the driving voltage of the device and inducing high efficiency and long lifespan. As described above, when the compound represented by Formula 1 of the present invention is applied as an organic layer material, preferably a light-emitting layer material (a blue,