Material for organic electroluminescent element, mixed material for organic electroluminescent element, and organic electroluminescent element
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- NIPPON STEEL CHEM & MATERIAL CO LTD
- Filing Date
- 2025-12-03
- Publication Date
- 2026-06-25
Smart Images
Figure JP2025042138_25062026_PF_FP_ABST
Abstract
Claims
1. A material for an organic electroluminescent device comprising a compound represented by the following general formula (1). Ar １ represents formula (2), formula (3), hydrogen, or deuterium. Ar ２ represents formula (2) or formula (3), and Ar １ and Ar ２ Among them, at least one represents formula (3). Ar ３ is represented by formula (3), or hydrogen, deuterium, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking 2 to 4 of these aromatic groups. R １ represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 11 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a dibenzothienyl group. R ２ ~R ４ each independently represents deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 11 carbon atoms, a substituted or unsubstituted dibenzofuranyl group, or a dibenzothienyl group. R ａ , R ｂ and R ｃ each independently represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms. x, y, and z represent the number of substituents, x represents an integer from 0 to 8, y represents an integer from 0 to 7, and z represents an integer from 0 to 8. * described in the above formula (2) or (3) indicates the bonding point with the above general formula (1). However, when Ar １ represents hydrogen or deuterium, Ar ２ and Ar ３ are both represented by the above formula (3), and at least one of the hydrogens in the compound represented by the above general formula (1) is substituted with deuterium.
2. Ar in the general formula (1) ３ The material for an organic electroluminescent element according to claim 1, characterized in that it is represented by a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted linked aromatic group formed by linking two to four of these aromatic groups.
3. The material for an organic electroluminescent device according to claim 1, characterized in that the general formula (1) is represented by any of the following formulas (5a) to (5f). Here, R ａ , R ｂ , R ｃ x, y, and z are the same as in the case of general formula (1) above. ５ Each of these independently represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms. ６ Each of these independently represents deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms. ｄ '' independently represents hydrogen and deuterium. 'n' represents the number of substituents and is an integer from 0 to 5. However, when the general formula (1) is represented by formula (5a), at least one of the hydrogen atoms in the compound represented by formula (5a) is substituted with deuterium.
4. The material for an organic electroluminescent element according to claim 1, characterized in that at least one of the hydrogen atoms in the compound represented by the general formula (1) is substituted with deuterium.
5. Ar in the general formula (1) １ Ar ２ or Ar ３ The organic electroluminescent material according to claim 1, characterized in that the average deuterated rate of at least one substituent among the substituents represented by is 20% or more.
6. The material for an organic electroluminescent element according to claim 1, characterized in that the average deuterated hydrogen content in the compound represented by the general formula (1) is 20% or more.
7. A mixed material for an organic electroluminescent element, characterized by comprising a compound represented by the general formula (1) described in claim 1 and a second compound different from the compound represented by the general formula (1).
8. A mixed material for an organic electroluminescent element, characterized by comprising the compound represented by the general formula (1) described in claim 1 and a linked carbazole compound represented by the following general formula (6). Here, Ar ４ R represents a substituted or unsubstituted tetraarylsilyl group having 24 to 42 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group composed of 2 to 8 of these aromatic groups linked together. ７ Each of these independently represents deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms. ７７ Each of these independently represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms. １ ~f ４ represents the number of substitutions, f ３ and f ４ These represent integers from 0 to 4 independently, and f １ and f ２ 'h' independently represents an integer from 0 to 3. 'g' represents a repeating number and independently represents an integer from 1 to 4. 'h' represents a substitution number and represents an integer of 1 or 2. When h is 2, general formula (6) may be symmetric or asymmetric. Some or all of the hydrogen atoms in the compound represented by general formula (6) may be substituted with deuterium. However, the compound represented by general formula (6) is a different compound from the compound represented by general formula (1).
9. An organic electroluminescent element comprising one or more organic layers between opposing anodes and cathodes, characterized in that at least one organic layer contains an organic electroluminescent element material comprising a compound represented by the general formula (1) described in claim 1.
10. An organic electroluminescent element comprising one or more light-emitting layers between opposing anodes and cathodes, characterized in that at least one light-emitting layer contains a light-emitting dopant and also contains an organic electroluminescent element material comprising the compound represented by the general formula (1) described in claim 1 as a host material.
11. An organic electroluminescent element comprising one or more organic layers between opposing anodes and cathodes, characterized in that at least one organic layer contains the mixed material for organic electroluminescent elements described in claim 8.
12. An organic electroluminescent element comprising one or more light-emitting layers between opposing anodes and cathodes, characterized in that at least one light-emitting layer contains a light-emitting dopant and the mixed material for organic electroluminescent elements described in claim 8 as a host material.
13. The organic electroluminescent element according to claim 11, characterized in that the organic layer containing the mixed material for the organic electroluminescent element is an emissive layer, and the emissive layer further contains a thermally activated delayed fluorescence emissive material.
14. The organic electroluminescent element according to claim 13, characterized in that the thermally activated delayed fluorescence material is a thermally activated delayed fluorescence material containing boron atoms.
15. The organic electroluminescent element according to claim 11, characterized in that the organic layer containing the mixed material for the organic electroluminescent element is an emissive layer, and the emissive layer further contains a phosphorescent material.
16. The organic electroluminescent device according to claim 15, characterized in that the phosphorescent material is a phosphorescent material containing platinum atoms or iridium atoms.
17. The organic electroluminescent element according to claim 11, wherein the organic layer containing the mixed material for the organic electroluminescent element is an emissive layer, and the emissive layer contains a thermally activated delayed fluorescence emissive material containing boron atoms and a phosphorescent emissive material containing platinum atoms or iridium atoms.
18. A premixed material for an organic electroluminescent element, obtained by pre-mixing the compound represented by the general formula (1) described in claim 1 with a linked carbazole compound represented by the following general formula (6). Here, Ar ４ R represents a substituted or unsubstituted tetraarylsilyl group having 24 to 42 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group composed of 2 to 8 of these aromatic groups linked together. ７ Each of these independently represents deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms. ７７ Each of these independently represents hydrogen, deuterium, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 36 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms. １ ~f ４ represents the number of substitutions, f ３ and f ４ These represent integers from 0 to 4 independently, and f １ and f ２ 'h' independently represents an integer from 0 to 3. 'g' represents a repeating number and independently represents an integer from 1 to 4. 'h' represents a substitution number and represents an integer of 1 or 2. When h is 2, general formula (6) may be symmetric or asymmetric. Some or all of the hydrogen atoms in the compound represented by general formula (6) may be substituted with deuterium. However, the compound represented by general formula (6) is a different compound from the compound represented by general formula (1).
19. The mixed material for an organic electroluminescent element according to 18, characterized in that the difference in the 50% weight loss temperature between the compound represented by general formula (1) and the linked carbazole compound represented by general formula (6) is 30°C or less.
20. A premixed material for an organic electroluminescent element, comprising pre-mixing the compound represented by the general formula (1) described in claim 1 with a luminescent dopant.
21. An organic electroluminescent element comprising one or more organic layers between opposing anodes and cathodes, characterized in that at least one organic layer contains the premixed material for organic electroluminescent elements described in claim 18.
22. A method for manufacturing an organic electroluminescent element, comprising an organic electroluminescent element having one or more organic layers between opposing anodes and cathodes, wherein at least one organic layer is a light-emitting layer, and the light-emitting layer is manufactured by depositing it from a single deposition source using the premixed material for organic electroluminescent elements described in claim 18.