US 9,812,651 B2
Condensed-cyclic compound and organic light-emitting device including the same
Jung-Sub Lee, Yongin (KR)
Assigned to Samsung Display Co., Ltd., Yongin, Gyeonggi-do (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin, Gyeonggi-Do (KR)
Filed on Jan. 5, 2015, as Appl. No. 14/589,027.
Claims priority of application No. 10-2014-0090351 (KR), filed on Jul. 17, 2014.
Prior Publication US 2016/0020396 A1, Jan. 21, 2016
Int. Cl. H01L 51/00 (2006.01); C07D 241/38 (2006.01); C07D 409/04 (2006.01); C07D 403/04 (2006.01); C07D 487/06 (2006.01); C07D 265/38 (2006.01); C07D 413/04 (2006.01); C07D 498/06 (2006.01); C07D 513/06 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0067 (2013.01) [C07D 241/38 (2013.01); C07D 265/38 (2013.01); C07D 403/04 (2013.01); C07D 409/04 (2013.01); C07D 413/04 (2013.01); C07D 487/06 (2013.01); C07D 498/06 (2013.01); C07D 513/06 (2013.01); H01L 51/0059 (2013.01); H01L 51/0072 (2013.01); H01L 51/0074 (2013.01); H01L 51/0081 (2013.01); H01L 51/0085 (2013.01); H01L 51/5016 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A condensed cyclic compound represented by Formula 1 below:

OG Complex Work Unit Drawing
wherein in Formulae 1,
X1 is selected from N(R1), C(R1)(R2), Si(R1)(R2), sulfur atom (S), oxygen atom (O), and P(R1);
X2 is selected from N(R3), C(R3)(R4), Si(R3)(R4), a sulfur atom (S), an oxygen atom (O), and P(R3);
i) X3 is a carbon atom that is one of X7 and X8 in Formula A below, X4 is a carbon atom that is the other of X7 and X8 in Formula A, X5 is C(R15), and X6 is C(R16), or ii) X5 is a carbon atom that is one of X7 and X8 in Formula A, X6 is a carbon atom that is the other of X7 and X8 in Formula A, X3 is C(R13), and X4 is C(R14);

OG Complex Work Unit Drawing
R1 to R4 and R11 to R19 are each independently selected from:
a hydrogen, a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 C3-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C3-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 C2-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), —B(Q6)(Q7), and —P(═O)(Q8)(Q9);
R1 and R12 are optionally linked to each other to form a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C3-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene, a substituted or unsubstituted C3-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
a11 is selected from 0, 1, 2, and 3;
a12 is selected from 0 and 1;
a19 is selected from 0, 1, 2, 3, and 4;
when a11 is 2 or more, a plurality of R11 are each independently identical or different,
when a13 is 2 or more, a plurality of R13 are each independently identical or different, and
when R19 are 2 or more, a plurality of R19 are each independently identical or different;
at least one substituent of the substituted C3-C10 cycloalkylene group, the substituted C3-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C3-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C2-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, 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 C3-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C3-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C2-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), and P(═O)(Q18)(Q19);
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), and P(═O)(Q28)(Q29); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), and —P(═O)(Q38)(Q39);
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 may be each independently a hydrogen, a 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.