US 12,245,496 B2
Light emitting device
Sun Young Pak, Suwon-si (KR); Taeil Kim, Hwaseong-si (KR); Junha Park, Gwacheon-si (KR); Jang Yeol Baek, Yongin-si (KR); Kyoung Sunwoo, Hwaseong-si (KR); Mun-Ki Sim, Seoul (KR); Chanseok Oh, Seoul (KR); and Minjung Jung, Gangwon-do (KR)
Assigned to SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Aug. 16, 2021, as Appl. No. 17/403,040.
Claims priority of application No. 10-2020-0181950 (KR), filed on Dec. 23, 2020.
Prior Publication US 2022/0209116 A1, Jun. 30, 2022
Int. Cl. H10K 85/60 (2023.01); C07F 5/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/13 (2023.01); H10K 50/15 (2023.01); H10K 50/18 (2023.01); H10K 59/12 (2023.01); H10K 59/38 (2023.01); H10K 85/30 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/322 (2023.02) [C07F 5/027 (2013.01); C09K 11/06 (2013.01); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A light emitting device, comprising:
a first electrode;
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region;
an electron transport region disposed on the emission layer; and
a second electrode disposed on the electron transport region, wherein
the emission layer comprises a fused polycyclic compound represented by Formula 1, and
the hole transport region comprises an amine compound represented by Formula H-a:

OG Complex Work Unit Chemistry
wherein in Formula 1,
X1 to X3 are each independently C(R4)(R5), N(R6), O, S, or Se,
R1 to R6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group of 2 to 30 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,
Ra and Rb are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group of 2 to 30 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,
n1 and n2 are each independently an integer from 0 to 4,
n3 is an integer from 0 to 2,
na is an integer from 0 to 4,
nb is an integer from 0 to 5,
Cy1 and Cy2 are each independently a group represented by Formula 2-1 or Formula 2-2, and
at least one of Cy1 and Cy2 is represented by Formula 2-1:

OG Complex Work Unit Chemistry
wherein in Formula 2-1,
Z1 is C(R9)(R10), N(R11), O, S, or Se,
R7 to R11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group of 2 to 30 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,
n4 is an integer from 0 to 4,
A1 is a position bonded to a boron atom in Formula 1, and
A2 are positions bonded X1 and X2 in Formula 1, or positions bonded to a nitrogen atom and X3 in Formula 1,

OG Complex Work Unit Chemistry
wherein in Formula 2-2,
R12 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted alkyl group of 2 to 30 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,
n5 is an integer from 0 to 3,
A3 is a position bonded to a boron atom in Formula 1, and
A4 are positions bonded to X1 and X2 in Formula 1, or positions bonded to a nitrogen atom and X3 in Formula 1,

OG Complex Work Unit Chemistry
wherein in Formula H-a,
Ya and Yb are each independently C(Re)(Rf), N(Rg), O, or S,
Ar1 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
L1 and L2 are each independently a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,
Ra to Rg are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or are combined with an adjacent group to form a ring,
na and nd are each independently an integer from 0 to 4, and
nb and nc are each independently an integer from 0 to 3.