US 12,486,452 B2
Organic electroluminescent element and electronic device
Hiromi Nakano, Sodegaura (JP); Hisato Matsumoto, Sodegaura (JP); Takushi Shiomi, Sodegaura (JP); Toshinari Ogiwara, Sodegaura (JP); and Keiji Okinaka, Sodegaura (JP)
Assigned to IDEMITSU KOSAN CO., LTD., Tokyo (JP)
Appl. No. 17/614,092
Filed by IDEMITSU KOSAN CO., LTD., Tokyo (JP)
PCT Filed May 25, 2020, PCT No. PCT/JP2020/020572
§ 371(c)(1), (2) Date Nov. 24, 2021,
PCT Pub. No. WO2020/241580, PCT Pub. Date Dec. 3, 2020.
Claims priority of application No. 2019-098828 (JP), filed on May 27, 2019.
Prior Publication US 2022/0231227 A1, Jul. 21, 2022
Int. Cl. C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/13 (2023.01); H10K 50/18 (2023.01); H10K 85/30 (2023.01); H10K 101/10 (2023.01); H10K 101/20 (2023.01)
CPC C09K 11/06 (2013.01) [H10K 85/60 (2023.02); H10K 85/615 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 50/13 (2023.02); H10K 50/181 (2023.02); H10K 85/322 (2023.02); H10K 85/626 (2023.02); H10K 2101/10 (2023.02); H10K 2101/20 (2023.02)] 31 Claims
 
1. An organic electroluminescence device comprising:
an anode;
a cathode;
an emitting layer provided between the anode and the cathode;
a first layer provided between the anode and the emitting layer and adjacent to the emitting layer; and
a second layer provided between the cathode and the emitting layer and adjacent to the emitting layer, wherein
the emitting layer comprises a first compound, a second compound, and a third compound,
the first layer comprises a compound represented by formula (1),
the second layer comprises a compound represented by formula (2),
the first compound is a fluorescent compound,
the second compound is a delayed fluorescent compound, and
a singlet energy S1(M1) of the first compound, a singlet energy S1(M2) of the second compound, and a singlet energy S1(M3) of the third compound satisfy a relationship of Numerical Formula 1,

OG Complex Work Unit Math

OG Complex Work Unit Chemistry
wherein
Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 are each independently a hydrogen atom or a substituent;
with the proviso that one of Ra1 to Ra5 is a substituent and the Ra1 to Ra5 not being a substituent are each hydrogen atoms and one of Rb1 to Rb5 is a substituent and the Rb1 to Rb5 not being a substituent are each hydrogen atoms,
Ra1 to Ra5, Rb1 to Rb5, and Rc3 to Rc5 serving as the substituent are each independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;
Rc1 is a hydrogen atom or a substituent, or is bonded to Rc2 to form a ring, and Rc1 serving as the substituent is a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms;
Rc2 is a hydrogen atom or a substituent, or a pair of Rc1 and Rc2 are mutually bonded to form a ring;
when a pair of Rc1 and Rc2 are mutually bonded to form a ring, the ring at least comprises a five-membered ring, the five-membered ring comprising at least one of a carbon atom, an oxygen atom, a sulfur atom, or a nitrogen atom;
Rc1 and Rc2 are not hydrogen atoms at the same time; and
Rc2 serving as the substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted amino group,
wherein
a partial structure represented by formula (1A) in formula (1) is a group represented by one of formulae (1A-1) and (1A-3) to (1A-10),

OG Complex Work Unit Chemistry
wherein
Rc1 represents the same as Rc1 in the formula (1), Rc2 represents the same as Rc2 in the formula (1), Rc3 to Rc5 each independently represent the same as Rc3 to Rc5 in the formula (1), and * represents a bonding position to a nitrogen atom in the compound represented by the formula (1),

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
where in the formulae (1A-1) and (1A-3) to (1A-10);
RA is a hydrogen atom or a substituent;
RA serving as the substituent is each independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;
when a plurality of RA are present, the plurality of RA are mutually the same or different; and * represents a bonding position to a nitrogen atom in the compound represented by the formula (1),

OG Complex Work Unit Chemistry
wherein
X1 to X3 are each independently a nitrogen atom or CR1, at least one of X1 to X3 is a nitrogen atom;
R1 is a hydrogen atom or a substituent;
R1 serving as the substituent is each independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms;
Ar1 and Ar2 are each independently represented by formula (2A), or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; and
A is represented by formula (2A) below,

OG Complex Work Unit Chemistry
wherein
HAr is represented by formula (2B);
a is 1, 2, 3, 4 or 5;
when a is 1, L1 is a single bond or a divalent linking group;
when a is 2, 3, 4 or 5, L1 is a trivalent to hexavalent linking group;
a plurality of HAr are mutually the same or different;
the linking group is a group derived from a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a group derived from a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a group derived from a group formed by mutually bonding two groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a group derived from a group formed by mutually bonding three groups selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; and
the mutually bonded groups are mutually the same or different,

OG Complex Work Unit Chemistry
wherein
X11 to X18 are each independently a nitrogen atom, CR13, or a carbon atom bonded to L1;
a plurality of R13 are mutually the same or different;
Y1 is an oxygen atom, a sulfur atom, NR18, SiR11R12, CR14R15, a nitrogen atom bonded to L1, a silicon atom bonded to each of R16 and L1, or a carbon atom bonded to each of R17 and L1;
among carbon atoms in X11 to X18, R11 to R12, and R14 to R15 as well as a nitrogen atom, a silicon atom, and carbon atoms in Y1, one atom is bonded to L1;
R11 and R12 are the same or different; R14 and R15 are the same or different;
R18 and R11 to R17 are each independently a hydrogen atom or a substituent, or at least one pair of a pair of adjacent ones of R13, a pair of R11 and R12, or a pair of R14 and R15 are bonded to each other to form a ring; and
R18 and R11 to R17 serving as the substituent are each independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.