CN-122029252-A - Organic light-emitting compound and organic electroluminescent device comprising the same

CN122029252ACN 122029252 ACN122029252 ACN 122029252ACN-122029252-A

Abstract

The present invention relates to a novel organic light emitting compound represented by chemical formula 1 (see description) and an organic electroluminescent device including the same, which may have high current efficiency and low driving voltage.

Inventors

SHEN XIANGEN
LI YIJIAN
Sun Xiaoshuo
Shen Zaiyi

Assignees

索路思高新材料有限公司

Dates

Publication Date: 20260512
Application Date: 20241126
Priority Date: 20231127

Claims (12)

1. An organic light emitting compound represented by the following formula 1: [ 1] Wherein in the formula 1, X 1 and X 2 are each independently N or CR, where R is hydrogen, an alkyl group containing 1 to 30 carbon atoms or an aryl group containing 6 to 60 carbon atoms, provided that one of X 1 and X 2 is N, and excluding the case where X 1 and X 2 are both N, Ar 1 to Ar 4 are each independently an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a heterocycloalkyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 60 carbon atoms, an alkylphosphine oxide group having 2 to 40 carbon atoms or an arylphosphino oxide group having 6 to 60 carbon atoms, each of which is unsubstituted or substituted, and L is an arylene group containing 6 to 60 carbon atoms, each of the arylene groups being unsubstituted or substituted.
2. The organic light-emitting compound according to claim 1, wherein X 1 and X 2 are each independently N or CH, provided that one of X 1 and X 2 is N, and excluding the case where both X 1 and X 2 are N, Ar 1 to Ar 4 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphinyl group having 2 to 20 carbon atoms or an arylphosphinyl group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphinyl group having 2 to 20 carbon atoms, an arylphosphinyl group having 6 to 30 carbon atoms, a nitrile group or a halogen group L is an arylene group having 6 to 30 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, an arylphosphino group having 6 to 30 carbon atoms, a nitrile group, or a halogen group.
3. The organic light-emitting compound according to claim 1, wherein X 1 and X 2 are each independently N or CH, provided that one of X 1 and X 2 is N, and excluding the case where both X 1 and X 2 are N, Ar 1 to Ar 4 are each independently an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 2 to 10 carbon atoms or an arylphosphino oxide group having 6 to 20 carbon atoms, each of which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylphosphine oxide group having 2 to 20 carbon atoms, an arylphosphino oxide group having 6 to 30 carbon atoms, a nitrile group or a halogen group, and L is an arylene group containing 6 to 20 carbon atoms, each of which is unsubstituted or substituted with a nitrile group.
4. The organic light-emitting compound according to claim 1, wherein X 1 and X 2 are each independently N or CH, provided that one of X 1 and X 2 is N, and excluding the case where both X 1 and X 2 are N, Ar 1 to Ar 4 are each independently phenyl, biphenyl, terphenyl, tolyl, naphthyl, phenanthryl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl or triphenylphosphine oxide, each of which is unsubstituted or substituted by methyl, phenyl, pyridyl, carbazolyl, bicyclononyl, adamantyl, cyclohexyl, dimethylphosphinyl, triphenylsilyl, nitrile or fluoro, or each of which is capable of forming a fused ring structure, and L is phenylene or naphthylene, each of which is unsubstituted or substituted with nitrile groups.
5. The organic light-emitting compound according to claim 1, wherein formula 1 is represented by the following formula 2 or formula 3: [ 2] [ 3] Wherein in the formulas 2 and 3, Ar 1 to Ar 4 are each independently phenyl, biphenyl, terphenyl, tolyl, naphthyl, phenanthryl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl or triphenylphosphine oxide, each of which is unsubstituted or substituted by methyl, phenyl, pyridyl, carbazolyl, bicyclononyl, adamantyl, cyclohexyl, dimethylphosphinyl, triphenylsilyl, nitrile or fluoro, or each of which is capable of forming a fused ring structure, and L is any one selected from the group consisting of formulas L-1 to L-15, [ L-1] [ L-2] [ L-3] [ L-4] [ L-5] [ L-6] [ L-7] [ L-8] [ L-9] [ L-10] [ L-11] [ L-12] [ Formula L-13] [ formula L-14] [ L-15] In each of formulas L-1 to L-15, * Represents a bonding site with formula 1.
6. The organic light-emitting compound according to claim 1, wherein formula 1 is represented by the following formula 2 or formula 3: [ 2] [ 3] Wherein in the formulas 2 and 3, Ar 1 to Ar 4 are each independently phenyl, biphenyl, tolyl, naphthyl, fluorenyl, dibenzofuranyl or carbazolyl, each of which is unsubstituted or substituted by methyl, phenyl or carbazolyl, and L is any one selected from the group consisting of the formulas L-1 to L-3 and L-5, [ L-1] [ L-2] [ L-3] [ L-5] In each of the formulae L-1 to L-3 and L-5, * Represents a bonding site with formula 1.
7. The organic light-emitting compound according to claim 1, wherein the organic light-emitting compound represented by formula 1 is any one selected from the following compounds 001 to 336: 。
8. an organic electroluminescent device comprising the organic light-emitting compound according to claim 1.
9. The organic electroluminescent device according to claim 8, comprising: an anode; A cathode; A light emitting layer disposed between the cathode and the anode, and An electron transport region disposed between the cathode and the light emitting layer, Wherein the electron transport region comprises the organic light emitting compound.
10. The organic electroluminescent device according to claim 9, wherein the electron transport region comprises at least one of an electron transport layer or an electron transport auxiliary layer, and The organic light-emitting compound is contained in at least one of the electron transport layer or the electron transport auxiliary layer.
11. Use of the organic light-emitting compound according to claim 1 for an organic electroluminescent device.
12. The use according to claim 11, wherein the organic light-emitting compound is used as an electron transport material for the organic electroluminescent device.

Description

Organic light-emitting compound and organic electroluminescent device comprising the same Cross Reference to Related Applications The present application claims priority and benefit from korean patent application No. 10-2023-0166706 filed on the date of 2023, 11 and 27 to the korean intellectual property agency, the entire disclosure of which is incorporated herein by reference. Technical Field Embodiments of the present disclosure relate to novel organic light emitting compounds and organic electroluminescent devices comprising the same. Background Since the first discovery of light emission of an organic film in Bernanose in 1950, research into an organic Electroluminescent (EL) device based on blue electroluminescence using anthracene single crystal was conducted in 1965, and Tang proposed an organic electroluminescent device having a stacked structure divided into functional layers including a hole layer and a light emitting layer in 1987. Thereafter, in order to impart high efficiency and long life to the device, organic electroluminescent devices including organic layers of respective characteristics and specific materials for the devices have been developed. When a voltage is applied between two electrodes in an organic electroluminescent device, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes combine with electrons, excitons are formed. When the excitons fall back to the ground state, light is emitted. In this case, the material for the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like according to its function. The light emitting materials for the organic electroluminescent device may be classified into blue, green and red light emitting materials according to the color of light. In addition, yellow and orange luminescent materials are also used as luminescent materials to achieve better natural colors. In addition, in order to improve color purity and luminous efficiency by energy transfer, host/dopant systems may be used as a light emitting material. Dopant materials can be classified into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Since such a phosphorescent material can theoretically improve the luminous efficiency four times that of a fluorescent material, a great deal of research is being conducted on phosphorescent host materials as well as phosphorescent dopant materials. NPB, BCP, alq 3 and the like shown below have been widely considered as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers so far, and anthracene derivatives have been reported as light-emitting layer materials. In particular, among the light emitting layer materials, metal complex compounds containing Ir such as Firpic, ir (ppy) 3 and (acac) Ir (btp) 2 shown below have an advantage of improved efficiency, which are used as blue, green and red phosphorescent dopant materials, and 4, 4-dicarbazole biphenyl (CBP) shown below is used as a phosphorescent host material. Therefore, the conventional organic layer material is advantageous in terms of light emitting characteristics, but is not satisfactory in terms of improving the life span of the organic electroluminescent device because of low glass transition temperature and thus very poor thermal stability. Therefore, there is a need to develop an organic layer material having excellent properties. Prior art literature Korean patent laid-open publication No. 10-2019-013391 Disclosure of Invention Technical problem Embodiments of the present disclosure provide novel compounds that can be used as materials for organic layers of organic electroluminescent devices having excellent heat resistance, carrier transporting ability, and the like, particularly as materials for electron transport layers, and uses thereof. Further, embodiments of the present disclosure provide an organic light emitting compound that exhibits high electron mobility by expanding a LUMO (lowest unoccupied molecular orbital) region and at the same time has a LUMO energy level suitable for use as a material for an organic layer of an organic electroluminescent device, particularly as a material for an electron transport layer. Embodiments of the present disclosure provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifetime, including novel organic light-emitting compounds. It should be noted that the objects of the present disclosure are not limited to the above-mentioned objects, and other non-mentioned objects of the present disclosure will be clearly understood by those skilled in the art from the following description. Technical proposal Embodiments of the present disclosure provide an or