Granted Patent B2

US 12,201,015 · App. 17/454,504 · Granted Jan 14, 2025

Inventors: Kazuhiro Nagayama (Tokyo, JP); Yoshiko Kajiyama (Tokyo, JP)

Assignee: Mitsubishi Chemical Corporation

H10K85/342C07F15/0033C09K11/06C09K2211/1029C09K2211/185H10K50/11H10K2101/10

Abstract

Claims (55)

1. An iridium complex compound denoted by a formula (1),

wherein,

Ir represents an iridium atom,

ring Cy 1 represents a monocyclic or fused aromatic ring or a monocyclic or fused heteroaromatic ring, which includes carbon atoms C 1 and C 2 ,

ring Cy 2 represents a monocyclic or fused heteroaromatic ring, which includes carbon atom C 3 and a nitrogen atom N 1 ,

each of R 1 and R 2 represents a hydrogen atom or a substituent,

a represents an integer of 0 or more, an upper limit of which is the maximum number of possible substituents on the ring Cy 1 ,

b represents an integer of 0 or more, an upper limit of which is the maximum number of possible substituents on the ring Cy 2 ,

when there are a plurality of R 1 and a plurality of R 2 , the plurality of R 1 and the plurality of R 2 are independent of each other and may be the same or may differ from each other, and

at least one R 1 is a substituent denoted by a formula (2) or a substituent further substituted with a substituent denoted by a formula (2),

wherein,

the broken line represents a bond,

each of ring Cy 3 , ring Cy 4 , and ring Cy 5 represents a monocyclic aromatic ring or a heteroaromatic ring,

ring Cy 3 optionally includes multiple linked ring structures,

each of R 3 to R 6 represents a hydrogen atom or a substituent,

each of x, y, and z represents an integer of 0 or more, an upper limit of which is the maximum number of possible substituents on the ring Cy 3 , the ring cy 4 , and the ring Cy 5 , respectively, and

two R 6 and a plurality of R 3 to a plurality of R 5 when there are a plurality of R 3 to a plurality of R 5 are independent of each other and may be the same or may differ from each other.

2. The iridium complex compound according to claim 1 , wherein the substituent denoted by the formula (2) is a substituent denoted by formula (3),

wherein,

each of R 3 to R 6 represents a hydrogen atom or a substituent, and

n represents an integer of 0 to 10.

3. The iridium complex compound according to claim 1 , wherein the substituent denoted by formula (2) is a substituent denoted by formula (4),

wherein,

each of R 3 to R 6 represents a hydrogen atom or a substituent.

4. The iridium complex compound according to claim 1 , wherein the substituent denoted by formula (2) is a substituent denoted by formula (2A),

wherein,

each of a ring Cy 3 , R 3 , R 4 , R 5 , R 6 , and x is as defined for formula (2).

5. The iridium complex compound according to claim 1 , wherein the substituent denoted by formula (2) is a substituent denoted by formula (3A),

wherein,

each of R 3 to R 6 represents a hydrogen atom or a substituent, and

n represents an integer of 0 to 10.

6. The iridium complex compound according to claim 1 , wherein the substituent denoted by formula (2) is a substituent denoted by formula (4A),

wherein each of R 3 to R 6 represents a hydrogen atom or a substituent.

7. The iridium complex compound according to claim 1 , wherein Cy 3 in the formula (2) has a partial structure denoted by formula (5),

wherein,

R 3 represents a hydrogen atom or a substituent,

and “*” represents a bonding position.

8. The iridium complex compound according to claim 1 , wherein the ring Cy 2 is a benzene ring.

9. The iridium complex compound according to claim 1 , wherein the ring Cy 2 is a pyridine ring.

10. The iridium complex compound according to claim 1 , wherein each of R 1 to R 6 is a hydrogen atom or a substituent selected from the group consisting of

D, F, Cl, Br, I, —N(R′), —CN, —NO 2 , —OH, —COOR′, —C(═O)R′, —C(═O)NR′, —P(═O)(R′) 2 , —S(═O)R′, —S(═O) 2 R′, —OSO 2 R′, a linear, branched, or cyclic alkyl group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkylthio group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 30 carbon atoms, a linear, branched, or cyclic alknyl group having 2 to 30 carbon atoms, an aromatic group having 5 to 60 carbon atoms, a heteroaromatic group having 5 to 60 carbon atoms, an aryloxy group having 5 to 40 carbon atoms, an arylthio group having 5 to 40 carbon atoms, an aralkyl group having 5 to 60 carbon atoms, a heteroaralkyl group having 5 to 60 carbon atoms, a diarylamino group having 10 to 40 carbon atoms, an arylheteroarylamino group having 10 to 40 carbon atoms, and a diheteroarylamino group having 10 to 40 carbon atoms,

wherein

the alkyl group, the alkoxy group, the alkylthio group, the alkenyl group, the alkynyl group, the aralkyl group, and the heteroaralkyl group may be further substituted with one or more R′, one —CH 2 — group or two or more non-adjacent —CH 2 — groups in these groups may be substituted with —C(—R′)═C(—R′)—, —C≡C—, —Si(—R′) 2 —, —C(O)—, —NR′—, —O—, —S—, —CONR′—, or a divalent aromatic group,

one or more hydrogen atoms in these groups may be substituted with D, F, Cl, Br, I, or —CN,

each of two adjacent R 1 to R 4 may be bonded to each other to form an aliphatic, aromatic, or heteroaromatic monocyclic ring or fused ring,

the aromatic group, the heteroaromatic group, the aryloxy group, the arylthio group, the diarylamino group, the arylheteroarylamino group, and the diheteroarylamino group may be further substituted with one or more R′,

wherein each R′ is independently selected from the group consisting of H, D, F, Cl, Br, I, —N(R″) 2 , —CN, —NO 2 , —Si(R″) 3 , —B(OR″) 2 , —C(═O)R″, —P(═O)(R″) 2 , —S(═O) 2 R″, —OSO 2 R″, a linear, branched, or cyclic alkyl group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkylthio group having 1 to 30 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 30 carbon atoms, a linear, branched, or cyclic alkynyl group having 2 to 30 carbon atoms, an aromatic group having 5 to 60 carbon atoms, a heteroaromatic group having 5 to 60 carbon atoms, an aryloxy group having 5 to 40 carbon atoms, an arylthio group having 5 to 40 carbon atoms, an aralkyl group having 5 to 60 carbon atoms, a heteroaralkyl group having 5 to 60 carbon atoms, a diarylamino group having 10 to 40 carbon atoms, an arylheteroarylamino group having 10 to 40 carbon atoms, and a diheteroarylamino group having 10 to 40 carbon atoms,

wherein the alkyl group, the alkoxy group, the alkylthio group, the alkenyl group, the alkynyl group, the aralkyl group, and the heteroaralkyl group may be further substituted with one or more R″, one CH 2 group or two or more non-adjacent CH 2 groups in these groups may be substituted with —R″C═CR′—′, —C≡C—, —Si(R″) 2 , —C(═O)—, —NR″—, —O—, —S—, —CONR″—, or a divalent aromatic group, one or more hydrogen atoms in these groups may be substituted with D, F, Cl, Br, I, or CN, and the aromatic group, the heteroaromatic group, the aryloxy group, the arylthio group, the diarylamino group, the arylheteroarylamino group, and the diheteroarylamino group may be further substituted with one or more R″,

each of two adjacent R′ may be bonded to each other to form an aliphatic, aromatic, or heteroaromatic monocyclic ring or fused ring, and

each R″ is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic group having 1 to 20 carbon atoms, and a heteroaromatic group having 1 to 20 carbon atoms, and two or more adjacent R″ may be bonded to each other to form an aliphatic, aromatic, or heteroaromatic, monocyclic or fused ring.

11. The iridium complex compound according to claim 1 , wherein at least one of R 1 is a substituent denoted by formula (2) or is further substituted with a substituent denoted by formula (2).

12. A composition comprising the iridium complex compound according to claim 1 and an organic solvent.

13. An organic electroluminescent element comprising the iridium complex compound according to claim 1 .

14. A display device comprising the organic electroluminescent element according to claim 13 .

15. An illumination device comprising the organic electroluminescent element according to claim 13 .

Assignments (1)

Priority Claims (1)

Continuity (2)

References Cited (58)