IP Library Granted Patent US 12692212
Granted Patent B2
US 12692212 · App. 17/918,737 · Granted Jul 28, 2026

Compound, organic electroluminescent element and electronic device

Inventors: Yuki Nakano (Tokyo, JP); Satomi Tasaki (Tokyo, JP); Kazuki Nishimura (Tokyo, JP); Hiroaki Itoi (Tokyo, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
C07C15/38C07C13/66C07D211/54C07D307/91C07D333/76H10K50/11H10K85/622H10K85/626H10K85/6572H10K85/6574H10K85/6576C07B2200/05
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Quick Facts
Patent No.
US 12692212
App. No.
17/918,737
Granted
Jul 28, 2026
Kind
B2
Abstract

A compound represented by a formula (1) and having at least one deuterium atom is provided. In the formula (1), n is 1 to 4, L 1 is a divalent group or a group represented by a formula (11) and R 111 to R 119 and R 211 to R 219 are each independently a hydrogen atom or a substituent, where the compound represented by the formula (1) does not include a group represented by —N(R 906 ) (R 907 ) and R 906 and R 907 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, or the like. In the formula (11), X 13 is an oxygen atom or a sulfur atom, Y 1 to Y 8 are each independently CR 300 or a nitrogen atom, and two of R 300 are a single bond bonded with *a or other L 1 and a single bond bonded with *b or other L 1 .

Claims (58)

1 . A compound represented by a formula (1) below and comprising at least one deuterium atom, and having a ratio of the number of deuterium atoms to a total number of hydrogen atoms being 30% or more,

where, in the formula (1): n is 1;

L 1 is a group represented by any one of formulae (L-1) to (L-3) below; and

R 111 to R 119 and R 211 to R 219 are each a hydrogen atom,

where, in the formulae (L-1) to (L-3):

one of two * represents a bonding position with *a in the formula (1) and the other * represents a bonding position with *b in the formula (1); and

R 11 to R 15 are each independently a hydrogen atom, an unsubstituted phenyl group, or an unsubstituted naphthyl group.

2 . The compound according to claim 1 , wherein

L 1 comprises at least one deuterium atom.

3 . The compound according to claim 1 , wherein

at least one of R 11 to R 15 is a deuterium atom.

4 . The compound according to claim 1 , wherein

at least one of R 11 to R 15 is a substituent, and at least one of R 11 to R 15 as the substituent each independently comprises one or more deuterium atom(s).

5 . The compound according to claim 1 , wherein

-(L 1 )n- is a group represented by a formula (L n -18) below,

where, in the formula (L n -18):

Ra is a hydrogen atom; and

one of two * represents a bonding position with *a in the formula (1) and the other * represents a bonding position with *b in the formula (1).

6 . The compound according to claim 5 , wherein

at least one of the plurality of Ra is a deuterium atom.

7 . The compound according to claim 1 , wherein

a total number of carbon atoms comprised in -(L 1 ) n- is 21 or less.

8 . The compound according to claim 1 , wherein

at least one of R 111 to R 119 or R 211 to R 219 is a deuterium atom.

9 . The compound according to claim 1 , wherein

R 111 to R 119 are each a deuterium atom, or

R 211 to R 219 are each a deuterium atom.

10 . The compound according to claim 1 , wherein

R 111 to R 119 and R 211 to R 219 are each a deuterium atom.

11 . An organic electroluminescence device comprising:

an anode;

a cathode; and

an emitting layer interposed between the anode and the cathode, wherein

the emitting layer comprises a compound M2 in a form of the compound according to claim 1 .

12 . The organic electroluminescence device according to claim 11 , wherein

the emitting layer further comprises a fluorescent compound M1.

13 . The organic electroluminescence device according to claim 11 , wherein

a singlet energy S 1 (M2) of the compound M2 and a singlet energy S 1 (M1) of the compound M1 satisfy a relationship of a numerical formula (Numerical Formula 1) below,

S 1 ( M 2)> S 1 ( M 1)  (Numerical Formula 1).

14 . The organic electroluminescence device according to claim 11 , wherein

the emitting layer comprises no metal complex.

15 . The organic electroluminescence device according to claim 11 , further comprising

a hole transporting layer between the anode and the emitting layer.

16 . The organic electroluminescence device according to claim 11 , further comprising

an electron transporting layer between the cathode and the emitting layer.

17 . An electronic device comprising the organic electroluminescence device according to claim 11 .

18 . The compound according to claim 1 , wherein

L 1 is a group represented by the formula (L-1).

19 . The compound according to claim 1 , wherein

the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the compound represented by the formula (1) is 40% or more.

20 . The compound according to claim 1 , wherein

the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the compound represented by the formula (1) is 50% or more.

21 . The compound according to claim 1 , wherein

the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the compound represented by the formula (1) is 60% or more.

22 . The compound according to claim 1 , wherein

the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the compound represented by the formula (1) is 70% or more.

23 . The compound according to claim 1 , wherein

the ratio of the number of deuterium atoms to the total number of hydrogen atoms of the compound represented by the formula (1) is 80% or more.