JP-2026074713-A - Compounds, compositions, organic electroluminescent devices, organic EL displays, and organic EL lighting

Abstract

[Problem] To provide a compound that has a good PL quantum yield, excellent solubility in organic solvents, can be used as a green light-emitting material, and has a good pot life for a composition containing the compound and an organic solvent. [Solution] A compound represented by the following formula 1. [Selection Diagram] Figure 1

Inventors

• 李 延軍
• 長山 和弘
• 長谷川 司
• 山下 麻未

Assignees

• 三菱ケミカル株式会社

Dates

Publication Date

20260507

Application Date

20241021

Claims (11)

1. The compound represented by formula 1 below. (In formula 1, X1 and X2 are independently N-R, O, or S. The R is an aromatic hydrocarbon group, an aromatic heterocyclic group, or an alkyl group. Benzene ring a and benzene ring b are each independently benzene rings which may have substituents. If X1 is N-R, then R may be bonded to the benzene ring a by -O-, -S-, -C(Ra a ) 2- , or by a single bond. If X2 is N-R, then R may be bonded to the benzene ring b by -O-, -S-, -C( Ra ) 2- , or by a single bond. Each of the R a groups is independently an alkyl group or an aromatic hydrocarbon group. Y1 , Y2 , and Y3 are each independently either CH or N, and at least one of them is N. G1 and G2 are each independently represented by the following equation 2. m1 and n1 are each independent integers between 0 and 3. m and n are each independent integers between 1 and 3. (In formula 2, R1 and R2 are each independently a C1-C12 alkyl group which may have substituents. * indicates the binding position with phenylene.
2. The compound according to claim 1, wherein m1 and n1 are each independently integers between 0 and 2.
3. The compound according to claim 1, wherein both m and n are 1.
4. The compound according to claim 1, wherein Y1 and Y2 are N.
5. The compound according to claim 1, wherein X1 and X2 are N-R.
6. The compound according to claim 5, wherein R is an aromatic hydrocarbon group.
7. The compound according to claim 1, represented by the following formula 3. (In formula 3, R3 , R4 , R5 , and R6 are each independently a hydrogen atom, an optionally substituted alkyl group, or an aromatic hydrocarbon group. Y11 , Y22 , and Y33 are each independently either CH or N, and at least one of them is N. G11 and G22 are each independently represented by formula 2. m² and n² are each independent integers between 1 and 3.
8. A composition comprising the compound described in any one of claims 1 to 7 and an organic solvent.
9. An organic electroluminescent device comprising the compound described in any one of claims 1 to 7.
10. An organic electroluminescent display device comprising the organic electroluminescent element described in claim 9.
11. Organic electroluminescent lighting comprising the organic electroluminescent element described in claim 9.

Description

This invention relates to compounds, compositions, organic electroluminescent devices, organic EL display devices, and organic EL lighting. In recent years, there has been active development of organic electroluminescent devices (OLEDs), which use organic thin films, as an alternative to those using inorganic materials. Organic electroluminescent devices (sometimes abbreviated as OLEDs) typically have a hole injection layer, hole transport layer, organic light-emitting layer, and electron transport layer between the anode and cathode. Suitable materials are being developed for each of these layers, and development is progressing in terms of emission colors, including red, green, and blue. There are two methods for forming the organic layer of an organic electroluminescent device: vacuum deposition and wet deposition (coating). Vacuum deposition offers advantages such as easy stacking, improved charge injection from the anode and/or cathode, and easier confinement of excitons within the light-emitting layer. On the other hand, wet deposition does not require a vacuum process, making it easy to create large-area layers. Furthermore, by using a coating solution containing a mixture of multiple materials with various functions, it is possible to easily form layers containing multiple materials with diverse functions. Therefore, in recent years, research and development of organic electroluminescent devices using coating methods has been actively pursued. The light-emitting layer of an organic electroluminescent device requires a compound that exhibits high luminous efficiency and a narrow full width at half maximum, and this compound also needs to be soluble in organic solvents used in wet film deposition methods. For example, Patent Document 1 describes a method to improve the solubility of a structure in which a six-membered aromatic heterocyclic group, such as an azine ring, is bonded to a DABNA skeleton by changing one of the substituents of the azine ring to an alkyl group such as a tert-butyl group, thereby reducing the molecular symmetry and increasing solubility. Patent Document 2 also describes a method to improve the solubility of a compound by adjusting the chain length or the number of substitutions of alkoxy groups or alkyl groups as substituents to an azine ring having acceptor function. International Publication No. 2022/092046International Publication No. 2022/121951 Figure 1 is a schematic cross-sectional view showing an example of the structure of the organic electroluminescent element of the present invention. The compound according to the embodiment of the present invention has the structure represented by Formula 1. (In formula 1, X1 and X2 are independently N-R, O, or S. The R is an aromatic hydrocarbon group, an aromatic heterocyclic group, or an alkyl group. Benzene ring a and benzene ring b are each independently benzene rings which may have substituents. If X1 is N-R, then R may be bonded to the benzene ring a by -O-, -S-, -C(Ra a ) 2- , or by a single bond. If X2 is N-R, then R may be bonded to the benzene ring b by -O-, -S-, -C( Ra ) 2- , or by a single bond. Each of the R a groups is independently an alkyl group or an aromatic hydrocarbon group. Y1 , Y2 , and Y3 are each independently either CH or N, and at least one of them is N. G1 and G2 are each independently represented by the following equation 2. m1 and n1 are each independent integers between 0 and 3. m and n are each independent integers between 1 and 3. (In formula 2, R1 and R2 are each independently a C1-C12 alkyl group which may have substituents. * indicates the binding position with phenylene. < X1 , X2 > X1 and X2 are independently N-R, O, or S. From the viewpoint of easily adjusting the emission wavelength to a preferred range, preferably at least one of X1 and X2 is N-R, and more preferably X1 and X2 are N-R. The R is an aromatic hydrocarbon group, an aromatic heterocyclic group, or an alkyl group. The number of carbon atoms in the aromatic hydrocarbon group is usually 6 or more, and usually 36 or less, preferably 30 or less, more preferably 24 or less, and even more preferably 18 or less. Examples of aromatic hydrocarbon groups include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenantrenyl, triphenylene, and naphthylphenyl groups. The number of carbon atoms in the aromatic heterocyclic group is usually 3 or more, preferably 4 or more, more preferably 5 or more, and usually 36 or less, preferably 30 or less, more preferably 24 or less, and even more preferably 18 or less. An aromatic heterocyclic group means an aromatic heterocyclic ring having at least one free electron valence. Examples of aromatic heterocyclic rings include pyridine rings, pyrimidine rings, pyrazine rings, triazine rings, imidazole rings, oxazole rings, thiazole rings, benzothiazole rings, benzoxazole rings, benzimidazole rings, quinoline rings, isoquinoline rings, quinoxaline rings, quinazoline rings, naphthyridine rings, and phenanth