US2023403928A1PendingUtilityA1
Heterocyclic compound and organic light-emitting device including the same
Est. expiryNov 26, 2038(~12.3 yrs left)· nominal 20-yr term from priority
H10K 85/40C07F 7/0814C07F 7/0812C09K 11/06C09K 2211/1018H10K 50/11H10K 50/12H10K 85/60H10K 85/631H10K 85/654H10K 85/6576H10K 85/6574H10K 85/342H10K 85/6572H10K 2101/10H10K 50/13H10K 50/15H10K 50/16H10K 50/17H10K 50/18H10K 50/165H10K 50/171H10K 2101/30H10K 85/636
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Claims
Abstract
A heterocyclic compound is represented by Formula 1. An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes at least one of the heterocyclic compound.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An organic light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and comprising an emission layer; and at least one heterocyclic compound represented by Formula 1:
wherein, in Formulae 1 and 2-1 to 2-7,
X 1 to X 3 are each independently N or C(R 15 ), wherein at least one selected from X 1 to X 3 is N,
L 1 to L 3 are each independently a substituted or unsubstituted C 3 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a1 to a3 are each independently an integer from 0 to 3,
Ar 1 to Ar 3 are each independently a group represented by one selected from Formulae 2-1 to 2-7,
R 1 to R 15 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
b3 is an integer from 0 to 3, b4 is an integer from 0 to 4, and b5 is an integer from 0 to 5,
of the groups included in the heterocyclic compound represented by Formula 1, at least one selected from the substituents R 1 to R 11 of the Formulae 2-1 to 2-7 is —Si(Q 1 )(Q 2 )(Q 3 ),
when Ar 1 is a group represented by Formula 2-7, a1 is 0, when Ar 2 is a group represented by Formula 2-7, a2 is 0, and when Ar 3 is a group represented by Formula 2-7, a3 is 0,
when Ar 1 is a group represented by Formula 2-7, Ar 2 and Ar 3 are not a group represented by Formula 2-1 and L 2 and L 3 are not a benzene group, when Ar 2 is a group represented by Formula 2-7, Ar 1 and Ar 3 are not a group represented by Formula 2-1 and L 1 and L 3 are not a benzene group, and when Ar 3 is a group represented by Formula 2-7, Ar 1 and Ar 2 are not a group represented by Formula 2-1 and L 1 and L 2 are not a benzene group, and
a case in which each of Ar 1 to Ar 3 is a group represented by Formula 2-1 is excluded,
at least one substituent of the substituted C 3 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 2 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 1 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ),
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group; and
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, and —Si(R a )(R b )(R c ),
R a to R c are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
* indicates a binding site to a neighboring atom.
2 . The organic light-emitting device of claim 1 , wherein:
the emission layer comprises a dopant and a host, the host comprises at least one of the heterocyclic compound, and the dopant is a phosphorescent dopant.
3 . The organic light-emitting device of claim 2 , wherein:
the dopant comprises platinum (Pt).
4 . The organic light-emitting device of claim 2 , wherein:
the dopant comprises an organometallic complex represented by Formula 401:
wherein, in Formulae 401 and 402,
M is platinum (Pt),
L 401 is selected from ligands represented by Formula 402, and xc1 is 1, 2, or 3, wherein, when xc1 is two or more, two or more L 401 (s) are identical to or different from each other,
L 402 is an organic ligand, and xc2 is an integer from 0 to 4, wherein, when xc2 is two or more, two or more L 402 (s) are identical to or different from each other,
X 401 to X 404 are each independently nitrogen or carbon,
X 401 and X 403 are linked via a single bond or a double bond, and X 402 and X 404 are linked via a single bond or a double bond,
A 401 and A 402 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
X 405 is a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q 411 )-*′, *—C(Q 411 )(Q 412 )-*′, *—C(Ω 411 )═C(Q 412 )-*′, *—C(Q 411 )=*′, or *═C(Q 411 )=*′, wherein Q 411 and Q 412 are each independently hydrogen, deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,
X 406 is a single bond, O, or S,
R 401 and R 402 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 1 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 1 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 401 )(Q 402 )(Q 403 ), —N(Q 401 )(Q 402 ), —B(Q 401 )(Q 402 ), —C(═O)(Q 401 ), —S(═O) 2 (Q 401 ), and —P(═O)(Q 401 )(Q 402 ), wherein Q 401 to Q 403 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 6 -C 20 aryl group, and a C 1 -C 20 heteroaryl group,
xc11 and xc12 are each independently an integer from 0 to 10, and
* and *′ in Formula 402 each indicate a binding site to M in Formula 401.
5 . The organic light-emitting device of claim 4 , wherein:
A 401 is C 1 -C 60 heterocyclic group containing at least one nitrogen.
6 . The organic light-emitting device of claim 4 , wherein:
X 405 and X 406 are each a single bond.
7 . The organic light-emitting device of claim 4 , wherein:
R 401 is not a hydrogen.
8 . A heterocyclic compound represented by Formula 1:
wherein, in Formulae 1 and 2-1 to 2-7,
X 1 to X 3 are each independently N or C(R 15 ), wherein at least one selected from X 1 to X 3 is N,
L 1 to L 3 are each independently a substituted or unsubstituted C 3 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a1 to a3 are each independently an integer from 0 to 3,
Ar 1 to Ar 3 are each independently a group represented by one selected from Formulae 2-1 to 2-7,
R 1 to R 15 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
b3 is an integer from 0 to 3, b4 is an integer from 0 to 4, and b5 is an integer from 0 to 5,
of the groups included in the heterocyclic compound represented by Formula 1, at least one selected from the substituents R 1 to R 11 of the Formulae 2-1 to 2-7 is —Si(Q 1 )(Q 2 )(Q 3 ),
when Ar 1 is a group represented by Formula 2-7, a1 is 0, when Ar 2 is a group represented by Formula 2-7, a2 is 0, and when Ar 3 is a group represented by Formula 2-7, a3 is 0,
when Ar 1 is a group represented by Formula 2-7, Ar 2 and Ar 3 are not a group represented by Formula 2-1 and L 2 and L 3 are not a benzene group, when Ar 2 is a group represented by Formula 2-7, Ar 1 and Ar 3 are not a group represented by Formula 2-1 and L 1 and L 3 are not a benzene group, and when Ar 3 is a group represented by Formula 2-7, Ar 1 and Ar 2 are not a group represented by Formula 2-1 and L 1 and L 2 are not a benzene group, and
a case in which each of Ar 1 to Ar 3 is a group represented by Formula 2-1 is excluded,
at least one substituent of the substituted C 3 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 2 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 1 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 1 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 1 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ),
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 110 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group; and
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 1 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 1 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with a C 1 -C 60 alkyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, and —Si(R a )(R b )(R c ),
R a to R c are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
* indicates a binding site to a neighboring atom.
9 . The heterocyclic compound of claim 8 , wherein:
at least one selected from Ar 1 to Ar 3 is a group that is different from the others thereof.
10 . The heterocyclic compound of claim 8 , wherein:
i) Ar 1 and Ar 2 are each a group represented by Formula 2-1, and Ar 3 is a group represented by Formula 2-3; ii) Ar 1 is a group represented by Formula 2-1, and Ar 2 and Ar 3 are each a group represented by Formula 2-3; iii) Ar 1 is a group represented by Formula 2-1, Ar 2 is a group represented by Formula 2-3, and Ar 3 is a group represented by Formula 2-4; iv) Ar 1 is a group represented by Formula 2-1, Ar 2 is a group represented by Formula 2-3, and Ar 3 is a group represented by Formula 2-3; v) Ar 1 is a group represented by Formula 2-1, and Ar 2 and Ar 3 are each a group represented by Formula 2-4; or vi) Ar 1 and Ar 2 are each a group represented by Formula 2-3, and Ar 3 is a group represented by Formula 2-6.
11 . The heterocyclic compound of claim 8 , wherein:
i) when Ar 1 is a group represented by Formula 2-1, at least one selected from R 1 (s) in the number of b5 is —Si(Q 1 )(Q 2 )(Q 3 ), and ii) when Ar 1 and Ar 2 are each a group represented by Formula 2-3 and Ar 3 is a group represented by Formula 2-6, at least one selected from R 10 (s) in the number of b4 and R 11 (s) in the number of b3 is —Si(Q 1 )(Q 2 )(Q 3 ).
12 . The heterocyclic compound of claim 11 , wherein:
at least one of Q 1 to Q 3 comprises at least one deuterium.
13 . The heterocyclic compound of claim 8 , wherein:
Ar 1 to Ar 3 are each independently a group represented by one selected from Formulae 2-1(1) to 2-1(3), 2-2(1) to 2-2(2), 2-3(1) to 2-3(2), 2-4(1) to 2-4(2), and 2-6(1) to 2-6(4):
wherein, in Formulae 2-1(1) to 2-1(3), 2-2(1) to 2-2(2), 2-3(1) to 2-3(2), 2-4(1) to 2-4(2), and 2-6(1) to 2-6(4),
Z 11 to Z 15 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bitluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a dibenzosilolyl group, and —Si(Q 31 )(Q 32 )(Q 33 ),
Q 31 to Q 33 are each independently selected from a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, and a pyridinyl group,
e3 is an integer from 0 to 3,
e4 is an integer from 0 to 4,
e5 is an integer from 0 to 5,
Ph indicates a phenyl group, and
* and *′ each indicate a binding site to a neighboring atom.
14 . The heterocyclic compound of claim 13 , wherein:
1) Ar 1 is a group represented by Formula 2-1(1), and Z 11 in Formula 2-1(1) is deuterium; 2) Ar 1 is a group represented by one selected from Formulae 2-1(2) and 2-1(3), and
i) Z 11 in Formulae 2-1(2) and 2-1(3) is deuterium;
ii) Z 12 in Formulae 2-1(2) and 2-1(3) is selected from deuterium and a benzene group substituted with deuterium;
iii) Z 12 and Z 13 in Formulae 2-1(2) and 2-1(3) are each independently selected from deuterium and a benzene group substituted with deuterium; or
iv) Z 11 to Z 14 in Formulae 2-1(2) and 2-1(3) are each independently selected from deuterium and a benzene group substituted with deuterium;
3) Ar 2 is a group represented by Formula 2-3(1), and
i) Z 11 in Formula 2-3(1) is deuterium; or
ii) Z 11 and Z 12 in Formula 2-3(1) are each deuterium; or
4) Ar 2 is a group represented by Formula 2-3(2), and
i) Z 11 in Formulae 2-1(2) and 2-1(3) is deuterium;
ii) Z 12 in Formulae 2-1(2) and 2-1(3) is selected from deuterium and a benzene group substituted with deuterium;
iii) Z 12 and Z 13 in Formulae 2-1(2) and 2-1(3) are each independently selected from deuterium and a benzene group substituted with deuterium; or
iv) Z 11 to Z 14 in Formulae 2-1(2) and 2-1(3) are each independently selected from deuterium and a benzene group substituted with deuterium.
15 . The heterocyclic compound of claim 13 , wherein:
at least one selected from Ar 1 to Ar 3 is a group represented by one selected from Formulae 2-1(2), 2-1(3), 2-2(2), 2-3(2), 2-6(3), and 2-6(4).
16 . The heterocyclic compound of claim 8 , wherein:
i) X 1 to X 3 are each N; ii) X 1 and X 2 are each N, and X 3 is C(R 15 ); iii) X 1 and X 3 are each N, and X 2 is C(R 15 ); iv) X 2 and X 3 are each N, and X 1 is C(R 15 ); v) X 1 is N, and X 2 and X 3 are each C(R 15 ); vi) X 2 is N, and X 1 and X 3 are each C(R 15 ); or vii) X 3 is N, and X 1 and X 2 are each C(R 15 ), and R 15 is hydrogen or deuterium.
17 . The heterocyclic compound of claim 8 , wherein:
at least one hydrogen atom in the heterocyclic compound represented by Formula 1 is substituted by a deuterium atom.
18 . The heterocyclic compound of claim 8 , wherein:
at least one of R 1 to R 15 in Formulae 2-1 to 2-7 comprises deuterium.
19 . The heterocyclic compound of claim 8 , wherein:
at least one of R 1 to R 15 is selected from: deuterium; a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group substituted with at least one deuterium; and —Si(Q 1 )(Q 2 )(Q 3 ); and wherein, Q 1 is selected from a phenyl group and a biphenyl group substituted with at least one deuterium, and Q 2 and Q 3 are each independently selected from a phenyl group; a biphenyl group; a phenyl group and a biphenyl group substituted with at least one deuterium.
20 . The heterocyclic compound of claim 8 , wherein:
i) R 1 is selected from deuterium; a phenyl group substituted with at least one deuterium; and —Si(Q 1 )(Q 2 )(Q 3 ); ii) R 4 and R 5 are each independently selected from deuterium; a phenyl group substituted with at least one deuterium; and —Si(Q 1 )(Q 2 )(Q 3 ); iii) R 6 and R 7 are each independently selected from deuterium; a phenyl group substituted with at least one deuterium; and —Si(Q 1 )(Q 2 )(Q 3 ); iv) R 10 and R 11 are each independently selected from deuterium; a phenyl group substituted with at least one deuterium; and —Si(Q 1 )(Q 2 )(Q 3 ); or v) R 12 to R 14 are each independently selected from deuterium; a phenyl group substituted with at least one deuterium; and —Si(Q 1 )(Q 2 )(Q 3 ); wherein, Q 1 is selected from a phenyl group and a biphenyl group substituted with at least one deuterium, and Q 2 and Q 3 are each independently selected from a phenyl group; a biphenyl group; a phenyl group and a biphenyl group substituted with at least one deuterium.Join the waitlist — get patent alerts
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