US 12,193,322 B2
Organic light-emitting devices
Hwan-Hee Cho, Yongin (KR); Mi-Kyung Kim, Yongin (KR); Se-Hun Kim, Yongin (KR); Dong-Hyun Kim, Yongin (KR); and Chang-Woong Chu, Yongin (KR)
Assigned to SAMSUNG DISPLAY CO., LTD., (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin (KR)
Filed on Nov. 16, 2020, as Appl. No. 17/099,679.
Application 17/099,679 is a continuation in part of application No. 14/691,521, filed on Apr. 20, 2015, granted, now 10,840,454.
Application 14/691,521 is a continuation in part of application No. 14/061,667, filed on Oct. 23, 2013, granted, now 9,012,903, issued on Apr. 21, 2015.
Claims priority of application No. 10-2013-0068640 (KR), filed on Jun. 14, 2013.
Prior Publication US 2021/0074924 A1, Mar. 11, 2021
Int. Cl. H10K 85/60 (2023.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 50/13 (2023.01); H10K 50/15 (2023.01)
CPC H10K 85/636 (2023.02) [C09K 11/02 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/633 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/13 (2023.02); H10K 50/15 (2023.02); H10K 85/615 (2023.02)] 13 Claims
 
1. An organic light-emitting device, comprising:
a substrate comprising a first sub-pixel region, a second sub-pixel region, and a third sub-pixel region;
a first sub-pixel electrode disposed in the first sub-pixel region of the substrate,
a first buffer layer disposed on the first sub-pixel electrode,
a first emission layer disposed on the first buffer layer,
a second sub-pixel electrode disposed in the second sub-pixel region of the substrate,
a second buffer layer disposed on the second sub-pixel electrode,
a second emission layer disposed on the second buffer layer,
a third sub-pixel electrode disposed in the third sub-pixel region of the substrate,
a third emission layer disposed on the third sub-pixel electrode, and
a second electrode disposed opposite to the first sub-pixel electrode, the second sub-pixel electrode, and the third sub-pixel electrode,
wherein the first emission layer emits a red color light, the second emission layer emits a green color light, and the third emission layer emits a blue color light, and only one of conditions (i) and (ii) below is met:
(i) the first emission layer comprises at least one light-emitting material represented by any one of Formulas 1 and 2, and
the second buffer layer consists of the at least one hole-transporting material represented by Formula 2(2), or
(ii) the second emission layer comprises at least one light-emitting material represented by any one of the Formulas 1 and 2, and
the first buffer layer consists of the at least one hole-transporting material represented by the Formula 2(2):

OG Complex Work Unit Chemistry
wherein, in the Formulae 1 and 2,
A1 is CR1 or N; A2 is CR2 or N; As is CR3 or N; A4 is CR4 or N; As is CR5 or N; A6 is CR6 or N; A7 is CR7 or N; As is CR8 or N; A9 is CR9 or N; A10 is CR10 or N; An is CR11 or N; A12 is CR12 or N; A13 is CR13 or N; A14 is CR14 or N; A15 is CR15 or N; and A16 is CR16 or N;
R1 to R16 are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a C1-C60 alkyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, and —N(Q1)(Q2)(Q3), Q1 to Q3 are each independently a C1-C60 alkyl group, a C6-C60 aryl group, or a C1-C60 heteroaryl group; or two or more of R1 to R16 are optionally connected to each other to form a C6-C20 saturated ring or a Co-C20 unsaturated ring;
Y is O, S, or C(R31)(R32);
L1 to L3 are each independently selected from the group consisting of a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, and a substituted or unsubstituted C1-C60 heteroarylene group;
n1 to n3 are each independently an integer of 0 to 3;
Ar1 to Ar3 are each independently selected from the group consisting of:
i) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, and —Si(Q1)(Q2)(Q3) (here, Q1 to Q3 are each independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group); and
ii) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and
—Si(Q1)(Q2)(Q3) (here, Q1 to Q3 are each independently a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C30 aryl group);
Z1 to Z4, R31, and R32 are each independently selected from the group consisting of:
i) a hydrogen atom, a deuterium atom, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
ii) 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 substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group;
iii) a C3-C10 cycloalkyl group, C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; and
iv) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; o1 to o4 are each independently an integer of 0 to 3;

OG Complex Work Unit Chemistry
wherein, in the Formula 2(2),
X11 is CR11 or N; X12 is CR12 or N; X13 is CR13 or N; X14 is CR14 or N; X15 is CR15 or N; X16 is CR16 or N; X17 is CR17 or N; X18 is CR18 or N; X19 is CR19 or N; X20 is CR20 or N; X21 is CR21 or N; X22 is CR22 or N; X23 is CR23 or N; and X24 is CR24 or N;
Z5, Z6, and R11 to R24 are each independently selected from the group consisting of:
i) a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl 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, and a C1-C60 alkoxy group;
ii) 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 substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group;
iii) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
iv) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; and
v) —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17) (here, Q11 and Q17 are each independently a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, or a C2-C60 heteroaryl group);
Ar13 and Ar14 are each independently selected from the group consisting of:
i) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; and
ii) a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, each substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl 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 C1-C10 heterocycloalkyl group, a Cs-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, and a C1-C60 heteroaryl group; Z11 and Z12 are connected to each other to form a fluorene moiety; and p and q are each independently an integer from 1 to 4.