US 11,696,458 B2
Organic light-emitting device and method of manufacturing the same
Seokhwan Hong, Seoul (KR); Seungyeon Kwak, Suwon-si (KR); Hyun Koo, Seongnam-si (KR); Sangdong Kim, Seongnam-si (KR); Sungjun Kim, Seongnam-si (KR); Jiwhan Kim, Seoul (KR); Sunghun Lee, Hwaseong-si (KR); Sukekazu Aratani, Hwaseong-si (KR); Sunyoung Lee, Seoul (KR); Shingo Ishihara, Suwon-si (KR); Aram Jeon, Suwon-si (KR); and Byoungki Choi, Hwaseong-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Nov. 21, 2018, as Appl. No. 16/197,710.
Claims priority of application No. 10-2017-0158568 (KR), filed on Nov. 24, 2017.
Prior Publication US 2019/0165292 A1, May 30, 2019
Int. Cl. H01L 51/00 (2006.01); H10K 50/11 (2023.01); C09K 11/06 (2006.01); C07F 15/00 (2006.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 71/00 (2023.01); H10K 85/30 (2023.01); H10K 101/40 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01); H10K 101/00 (2023.01)
CPC H10K 50/11 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 71/00 (2023.02); H10K 85/346 (2023.02); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02); H10K 2101/90 (2023.02)] 13 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode;
an emission layer comprising a host and a dopant, the emission layer disposed between the first electrode and the second electrode;
a hole transport region disposed between the first electrode and the emission layer; and
an electron transport region disposed between the emission layer and the second electrode,
wherein the dopant comprises platinum or palladium, and a tetradentate organic ligand including a benzimidazole and a pyridine group, a dopant concentration profile of the emission layer satisfies N1≤Dcon(x)≤N2 in a direction from the hole transport region toward the electron transport region,
wherein the dopant concentration profile of the emission layer is continuous,
x of Dcon(x) is a real number and a variable satisfying 0≤x≤LEML,
LEML is a thickness of the emission layer,
Dcon(x) represents a dopant concentration (percent by weight) in the emission layer at a distance x from an interface between the hole transport region and the emission layer to an interface between the electron transport region and the emission layer,
N1 is a minimum value of a dopant concentration of the emission layer and is in a range of about 1 percent by weight to about 10 percent by weight,
N2 is a maximum value of the dopant concentration of the emission layer and is greater than about 10 percent by weight and less than or equal to about 40 percent by weight,
wherein Dcon(0) and Dcon(LEML) are each N2,
wherein the dopant is represented by Formula 1A-1:

OG Complex Work Unit Chemistry
wherein in Formula 1A-1,
M represents the palladium or the platinum,
X1 is O or S, and a bond between X1 and M is a covalent bond, X2 is N, and X3 is C,
X11 is N or C-[(L11)b11-(R11)c11], X12 is N or C-[(L12)b12-(R12)c12], X13 is N or C-[(L13)b13-(R13)c13], and X14 is N or C-[(L14)b14-(R14)c14],
X21 is N or C-[(L21)b21-(R21)c21], X22 is N or C-[(L22)b22-(R22)c22], and X23 is N or C-[(L23)b23-(R23)c23],
X31 is N or C-[(L31)b31-(R31)c31], X32 is N or C-[(L32)b32-(R32)c32], and X33 is N or C-[(L33)b33-(R33)c33],
X41 is N or C-[(L41)b41-(R41)c41], X42 is N or C-[(L42)b42-(R42)c42], X43 is N or C-[(L43)b43-(R43)c43], and X44 is N or C-[(L44)b44-(R44)c44], and X51 is N-[(L7)b7-(R7)c7], wherein
L7, L11 to L14, L21 to L23, L31 to L33, and L41 to L44, are independently a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group,
b11 to b14, b21 to b23, b31 to b33, and b41 to b44, are independently an integer of 0 to 5, and b7 is 0,
R7 is a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
R11 to R14, R21 to R23, R31 to R33, and R41 to R44, are independently hydrogen, deuterium, —F, a hydroxyl group, a cyano group, a nitro group, an amidino group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
c7 is 1, and c11 to c14, c21 to c23, c31 to c33, and c41 to c44, are independently an integer of 1 to 5, and
optionally, at least two of R11 to R14 are linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
optionally, at least two of R21 to R23 are linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
optionally, at least two of R31 to R33 are linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, or
optionally, at least two of R41 to R44 are linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group.