US 11,758,802 B2
Composition and organic light-emitting device including the same
Banglin Lee, Suwon-si (KR); Soyeon Kim, Seoul (KR); Jiyoun Lee, Anyang-si (KR); Jongwon Choi, Yongin-si (KR); Dmitry Kravchuk, Hwaseong-si (KR); Sangdong Kim, Seongnam-si (KR); Sukekazu Aratani, Hwaseong-si (KR); and Yongsuk Cho, Hwaseong-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Oct. 31, 2019, as Appl. No. 16/669,770.
Claims priority of application No. 10-2019-0037214 (KR), filed on Mar. 29, 2019; and application No. 10-2019-0136949 (KR), filed on Oct. 30, 2019.
Prior Publication US 2020/0313095 A1, Oct. 1, 2020
Int. Cl. H10K 85/30 (2023.01); C07D 403/14 (2006.01); C07D 487/04 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/342 (2023.02) [C07D 403/14 (2013.01); C07D 487/04 (2013.01); C07F 15/0033 (2013.01); C09K 11/06 (2013.01); H10K 85/6572 (2023.02); C09K 2211/1018 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 17 Claims
OG exemplary drawing
 
1. A composition comprising a first compound and a second compound, wherein the first compound comprises a compound represented by Formula 1, and the second compound comprises a compound represented by Formula 2:

OG Complex Work Unit Chemistry
Y2 in Formula 1 is C,
a group represented by

OG Complex Work Unit Chemistry
 in Formula 1 is a group represented by Formula A(1):

OG Complex Work Unit Chemistry
wherein, in Formula A(1), R9 and R11 are each independently a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, or a phenyl group, each unsubstituted or substituted with deuterium, a C1-C20 alkyl group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a phenyl group, or any combination thereof, and R10 and R12 are each independently hydrogen or deuterium, *′ indicates a binding site to Ir in Formula 1, and *″ indicates a binding site to a neighboring atom in Formula 1,
Ar1 in Formula 2 is a C5-C6, carbocyclic group unsubstituted or substituted with at least one R61 or a C1-C6 heterocyclic group unsubstituted or substituted with at least one R61,
Ar2 in Formula 2 is a π electron-depleted nitrogen-containing C1-C6 cyclic group unsubstituted or substituted with at least one R62,
Ar5 in Formula 2 is not present or is a single bond, a C5-C6 carbocyclic group unsubstituted or substituted with at least one R65, or a C1-C6 heterocyclic group unsubstituted or substituted with at least one R65,
n in Formula 2 is 1, 2, or 3, and when n is 1, Ar5 is not present,
a1 and a2 in Formula 2 are each independently an integer from 0 to 5, and the sum of a1 and a2 is 1 or greater,
ring CY2 and ring CY3 in Formula 2 are each independently a C5-C6, carbocyclic group or a C1-C6 heterocyclic group, and ring CY2 and ring CY3 are optionally bound to each other via a C5-C6 carbocyclic group unsubstituted or substituted with at least one R66 or a C1-C6 heterocyclic group unsubstituted or substituted with at least one R6,
R1 to R8, A1 to A7, R20, R30, R61, R62, R65, and R66 in Formulae 1 and 2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
b2 and b3 in Formula 2 are each independently an integer from 0 to 20, when b2 is 2 or more, two or more R20(s) are identical to or different from each other, and when b3 is 2 or more, two or more R30(s) are identical to or different from each other,
provided that at least one of R1 to R8 is a fluoro (—F) group,
two or more of R1 to R8 in Formula 1 are optionally linked to form a C5-C60 carbocyclic group which is unsubstituted or substituted with at least one R1a or a C1-C60 heterocyclic group which is unsubstituted or substituted with at least one R1a,
two or more of A1 to A7 in Formula 1 are optionally linked to form a C5-C60 carbocyclic group which is unsubstituted or substituted with at least one R1a or a C1-C60 heterocyclic group which is unsubstituted or substituted with at least one R1a,
two or more of ring CY2, ring CY3, R20, and R30 in Formula 2 are optionally linked to form a C5-C60 carbocyclic group which is unsubstituted or substituted with at least one R1a or a C1-C60 heterocyclic group which is unsubstituted or substituted with at least one R1a,
R1a is understood by referring to the description of A7 provided above, and
a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C2-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof,
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro 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 C1-C60 alkyl group, unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C2-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group, unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.