KR-20260068064-A - Compounds, organic EL elements, display devices, and lighting devices

Abstract

The present invention aims to provide an organic EL device with excellent luminous efficiency and durability. The present invention comprises a compound represented by the following general formula (1) or a compound represented by the general formula (3).

Inventors

• 고바야시, 가즈키
• 나가오, 가즈마사
• 도쿠다, 다카시

Assignees

• 도레이 카부시키가이샤

Dates

Publication Date

20260513

Application Date

20240903

Priority Date

20230907

Claims (17)

1. A compound represented by the following general formula (1). (In general formula (1), R 11 and R 12 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.) L1 is an unsubstituted phenylene group, an unsubstituted naphthylene group, an unsubstituted pyridylene group, an unsubstituted pyridazylene group, an unsubstituted pyrazylene group, or an unsubstituted pyrimidylene group, and L2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyridazylene group, a substituted or unsubstituted pyrazylene group, or a substituted or unsubstituted pyrimidylene group. R 13 to R 16 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. provided that at least one of R 14 and R 15 is a group represented by the following general formula (2). (In general formula (2), X1 to X5 are each independently CR1 to CR5 or a nitrogen atom. R1 to R5 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. provided that any one of X1 to X5 is a nitrogen atom.)
2. A compound represented by the following general formula (3). (In general formula (3), R 21 and R 22 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group and are connected to each other to form a ring structure. L 1 is an unsubstituted phenylene group, an unsubstituted naphthylene group, an unsubstituted pyridylene group, an unsubstituted pyridazilene group, an unsubstituted pyrazylene group or an unsubstituted pyrimidylene group, and L 2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyridazilene group, a substituted or unsubstituted pyrazylene group, or a substituted or unsubstituted pyrimidylene group. R 23 to R 26 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. provided that R 24 and R 25 are groups represented by the following general formula (2). (In general formula (2), X1 to X5 are each independently CR1 to CR5 or a nitrogen atom. R1 to R5 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. provided that any one of X1 to X5 is a nitrogen atom.)
3. A compound according to claim 1, wherein R 11 and R 12 in the above general formula (1) are each independently a methyl group, a phenyl group, a naphthyl group, or a pyridyl group.
4. A compound according to claim 1, wherein R 14 and R 15 in the above general formula (1) are each independently represented by general formula (2).
5. A compound according to claim 1 or 2, wherein in the above general formula (2), one of X 1 to X 5 is a nitrogen atom and the others are methine groups.
6. An organic EL device having at least an electron transport layer and a light-emitting layer between an anode and a cathode, emitting light by electrical energy, wherein the electron transport layer contains a compound described in claim 1 or 2.
7. An organic EL device according to claim 6, wherein the electron transport layer further comprises an alkali metal, a rare earth metal, or a complex of an alkali metal and an organic material.
8. An organic EL device having at least a charge generating layer and a light emitting layer between an anode and a cathode, and emitting light by electrical energy, wherein the charge generating layer contains a compound described in claim 1 or 2.
9. An organic EL device according to claim 8, wherein the charge generating layer further contains a phenanthroline derivative.
10. An organic EL device according to claim 8, wherein the charge generating layer further comprises an alkali metal or a rare earth metal.
11. An organic EL device according to claim 10, wherein the alkali metal is Li.
12. An organic EL device according to claim 10, wherein the rare earth metal is Yb.
13. An organic EL device having at least an electron injection layer and a light-emitting layer between an anode and a cathode, emitting light by electrical energy, wherein the electron injection layer contains a compound described in claim 1 or 2.
14. An organic EL device according to claim 13, wherein the electron injection layer further contains an alkali metal or a rare earth metal.
15. An organic EL device according to claim 6, wherein the light-emitting layer contains a compound represented by the following general formula (4). (In general formula (4), the Za ring, Zb ring and Zc ring are each independently a substituted or unsubstituted ring-forming aryl ring having 6 to 30 carbon atoms or a substituted or unsubstituted ring-forming heteroaryl ring having 5 to 30 atoms; Z1 and Z2 are each independently an oxygen atom, NRa (a nitrogen atom having the substituent Ra) or a sulfur atom, and if Z1 is NRa, it may or may not form a ring by combining with the A ring or B ring, and if Z2 is NRa, it may or may not form a ring by combining with the B ring or C ring; Ra is each independently a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heteroaryl group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Y is a boron atom, a phosphorus atom, or SiRb (having the substituent Rb) silicon atom), P=O or P=S; Rb is, each independently, selected from a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heteroaryl group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.)
16. A display device comprising an organic EL element as described in paragraph 6.
17. A lighting device comprising an organic EL element as described in paragraph 6.

Description

Compounds, organic EL elements, display devices, and lighting devices The present invention relates to a compound, an organic EL element using the same, a display device, and a lighting device. Organic EL devices have been steadily advancing toward practical application, such as being adopted in displays for televisions and smartphones in recent years. However, there are still many technical challenges with existing organic EL devices. Among them, achieving both high-efficiency light emission and a long lifespan for organic EL devices is a major challenge. As compounds that solve these problems, phosphine oxide derivatives having a phosphine oxide backbone and an anthracene backbone (e.g., see Patent Documents 1 and 2), phosphine oxide derivatives having a dibenzofuran backbone or a dibenzothiophene backbone (e.g., see Patent Document 3), phosphine oxide derivatives in which the linker is substituted with a diphenylphosphine group (e.g., see Patent Document 4), and phosphine oxide derivatives having a bipyridine group and a ring-shaped structure (e.g., see Patent Document 5) have been developed. Suitable embodiments of the compound, light-emitting element, display device, and lighting device according to the present invention are described in detail below. However, the present invention is not limited to the following embodiments and can be implemented with various modifications depending on the purpose or use. (Compound represented by general formula (1)) The compound according to Embodiment 1 of the present invention is a compound represented by the general formula (1). In general formula (1), R 11 and R 12 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. L1 is an unsubstituted phenylene group, an unsubstituted naphthylene group, an unsubstituted pyridylene group, an unsubstituted pyridazylene group, an unsubstituted pyrazylene group, or an unsubstituted pyrimidylene group, and L2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyridazylene group, a substituted or unsubstituted pyrazylene group, or a substituted or unsubstituted pyrimidylene group. R 13 to R 16 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. provided that at least one of R 14 and R 15 is a group represented by the following general formula (2). In general formula (2), X1 to X5 are each independently CR1 to CR5 or a nitrogen atom. R1 to R5 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. However, any one of X1 to X5 is a nitrogen atom. (Compound represented by general formula (3)) The compound according to Embodiment 2 of the present invention is a compound represented by the general formula (3). In general formula (3), R 21 and R 22 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and are connected to each other to form a ring structure. L1 is an unsubstituted phenylene group, an unsubstituted naphthylene group, an unsubstituted pyridylene group, an unsubstituted pyridazylene group, an unsubstituted pyrazylene group, or an unsubstituted pyrimidylene group, and L2 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyridazylene group, a substituted or unsubstituted pyrazylene group, or a substituted or unsubstituted pyrimidylene group. R 23 to R 26 are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a phosphoryl group, a halogen atom, a cyano group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. provided, however, that R 24 and R 25 are groups represented by the general formula (2) as described in the description of the compound according to Example 1. The following description applies to the compounds of Embodiments 1 and 2, unless otherwise specifically noted. In all of the above groups, the hydrogen atom may be a deuterium atom. In the compound or partial structure described below, the same applies to cases described as "substituted or unsubstituted." An alkyl group refers to a saturated aliphatic hydrocarbon group, such as a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl g