US 12,284,916 B2
Organic electroluminescence device and electronic apparatus provided with the same
Hiroaki Itoi, Sodegaura (JP); Yuki Nakano, Sodegaura (JP); Satomi Tasaki, Sodegaura (JP); Taro Yamaki, Sodegaura (JP); and Tetsuya Masuda, Sodegaura (JP)
Assigned to IDEMITSU KOSAN CO., LTD., Tokyo (JP)
Appl. No. 17/602,273
Filed by IDEMITSU KOSAN CO., LTD., Tokyo (JP)
PCT Filed Apr. 8, 2020, PCT No. PCT/JP2020/015850
§ 371(c)(1), (2) Date Oct. 7, 2021,
PCT Pub. No. WO2020/209299, PCT Pub. Date Oct. 15, 2020.
Claims priority of application No. 2019-073768 (JP), filed on Apr. 8, 2019.
Prior Publication US 2022/0165964 A1, May 26, 2022
Int. Cl. H01L 51/00 (2006.01); C07D 307/77 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6574 (2023.02) [C07D 307/77 (2013.01); C09K 11/06 (2013.01); H10K 85/615 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 18 Claims
OG exemplary drawing
 
1. An organic electroluminescence device comprising:
a cathode,
an anode, and
an organic layer disposed between the cathode and the anode, wherein
the organic layer comprises an emitting layer, a first layer, and a second layer,
the first layer is disposed between the cathode and the emitting layer,
the second layer is disposed between the cathode and the first layer,
the second layer comprises a compound represented by the following formula (EB4),
the emitting layer comprises a compound represented by the following formula (1), and
the first layer comprises a compound represented by the following formula (BE1):

OG Complex Work Unit Chemistry
wherein in the formula (1),
X1 is an oxygen atom or a sulfur atom;
Ar1 is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
L1 is a single bond,
a substituted or unsubstituted arylene group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted divalent heterocyclic group including 5 to 50 ring atoms;
R1 to R8 and R11 to R19 are independently
a hydrogen atom, a halogen atom, a cyano group, a nitro group,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group including 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R901)(R902)(R903),
—O—(R904),
—S—(R905),
—N(R906)(R907),
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R901 to R907 are independently
a hydrogen atom,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms; and
when two or more of each of R901 to R907 are present, the two or more of each of R901 to R907 are the same or different;

OG Complex Work Unit Chemistry
wherein in the formula (BE1),
two or more of X31 to X33 are nitrogen atoms, and the rest which is not a nitrogen atom is CR;
R is
a hydrogen atom,
a cyano group,
a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,
—Si(R901)(R902)(R903),
—O—(R904),
a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or
a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
R901 to R904 are as defined in the formula (1);
when a plurality of R's are present, the plurality of R's may be the same as or different from each other;
AE is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
BE is a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
LE is a single bond, a substituted or unsubstituted (nE+1)-valent aromatic hydrocarbon ring group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted (nE+1)-valent heterocyclic group including 5 to 50 ring atoms; the aromatic hydrocarbon ring group may have a structure in which two or more different aromatic hydrocarbon rings are bonded;
CE's are independently a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group including 5 to 50 ring atoms;
nE is an integer of 1 to 3; and when nE is 2 or more, LE is not a single bond;

OG Complex Work Unit Chemistry
wherein in the formula (EB4),
ArE1 and ArE3 are independently
a single bond,
a substituted or unsubstituted phenylene group,
a substituted or unsubstituted naphthylene group,
a substituted or unsubstituted phenanthrylene group, or
a substituted or unsubstituted anthrylene group;
ArE2 and ArE4 are independently
a substituted or unsubstituted phenyl group,
a substituted or unsubstituted naphthyl group,
a substituted or unsubstituted phenanthryl group, or
a substituted or unsubstituted anthryl group;
ArE1 and ArE2, and ArE3 and ArE4 independently form a substituted or unsubstituted, saturated or unsaturated ring constituted only by a 6-membered ring by bonding with each other, or do not form a ring.