US 12,480,041 B2
Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
Yusuke Takahashi, Sodegaura (JP); Tasuku Haketa, Sodegaura (JP); and Shota Tanaka, Sodegaura (JP)
Assigned to IDEMITSU KOSAN CO., LTD., Chiyoda-ku (JP)
Appl. No. 17/634,498
Filed by IDEMITSU KOSAN CO., LTD., Chiyoda-ku (JP)
PCT Filed Sep. 29, 2021, PCT No. PCT/JP2021/035944
§ 371(c)(1), (2) Date Feb. 10, 2022,
PCT Pub. No. WO2022/071424, PCT Pub. Date Apr. 7, 2022.
Claims priority of application No. 2020-165196 (JP), filed on Sep. 30, 2020; and application No. 2020-204495 (JP), filed on Dec. 9, 2020.
Prior Publication US 2023/0262999 A1, Aug. 17, 2023
Int. Cl. C07C 211/54 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 85/60 (2023.01)
CPC C09K 11/06 (2013.01) [C07C 211/54 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 85/626 (2023.02); H10K 85/631 (2023.02); H10K 85/633 (2023.02); C07B 2200/05 (2013.01)] 20 Claims
 
1. A compound represented by formula (1):

OG Complex Work Unit Chemistry
wherein:
N* is a central nitrogen atom,
R1 to R7 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
Ra and Rb are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
wherein adjacent two selected from R1 to R7, Ra and Rb are not bonded to each other, thereby failing to form a ring structure,
L is a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, Ar1 is represented by formula (1-a) and Ar2 is represented by formula (1-b) or (1-c):

OG Complex Work Unit Chemistry
wherein:
R11 to R18, R21 to R25, and R31 to R35 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein:
one selected from R11 to R18 is a single bond bonded to *a,
one selected from R21 to R25 is a single bond bonded to *b,
one selected from R31 to R35 is a single bond bonded to *c,
* is a bonding site to the central nitrogen atom N*
m1 is 0 or 1, n1 is 0 or 1,
when m1 is 0 and n1 is 0, *c is bonded to the central nitrogen atom N*,
when m1 is 0 and n1 is 1, *b is bonded to the central nitrogen atom N* and *c is bonded to R33,
when m1 is 1 and n1 is 0, *c is bonded to R23,
when m1 is 1 and n1 is 1, *c is bonded to R33,
R11 to R18 not the single bond, R21 to R25 not the single bond, and R31 to R35 not the single bond are not bonded to each other, thereby failing to form a ring structure,

OG Complex Work Unit Chemistry
wherein:
R41 to R48, R51 to R55, and R61 to R65 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein:
one selected from R41 to R48 is a single bond bonded to *d,
one selected from R51 to R55 is a single bond bonded to *e,
one selected from R61 to R65 is a single bond bonded to *f,
* is a bonding site to the central nitrogen atom N*,
m2 is 0 or 1 and n2 is 0 or 1,
when m2 is 0 and n2 is 0, *f is bonded to the central nitrogen atom N*,
when m2 is 0 and n2 is 1, *e is bonded to the central nitrogen atom N* and *f is bonded to R63,
when m2 is 1 and n2 is 0, *f is bonded to R53,
when m2 is 1 and n2 is 1, *f is bonded to R63,
R41 to R48 not the single bond, R51 to R55 not the single bond and R61 to Re not the single bond are not bonded to each other, thereby failing to form a ring structure,

OG Complex Work Unit Chemistry
wherein:
R71 to R75, R81 to R86, and R91 to R95 are each independently
a hydrogen atom, a halogen atom, a nitro group, a cyano group,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms,
a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms,
a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms,
a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or
a mono-, di- or tri-substituted silyl group wherein the substituent is selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
wherein;
one selected from R71 to R75 is a single bond bonded to *g,
one selected from R81 to R86 is a single bond bonded to *h and another one selected from R81 to R86 is a single bond bonded to *i,
* is a bonding site to the central nitrogen atom N*,
R71 to R75 not the single bond, R51 to R86 not the single bond, and R91 to R95 are not bonded to each other, thereby failing to form a ring structure.