US 11,818,932 B2
Organic light-emitting device
Jino Lim, Yongin-si (KR); Seulong Kim, Yongin-si (KR); Younsun Kim, Yongin-si (KR); Dongwoo Shin, Yongin-si (KR); Jungsub Lee, Yongin-si (KR); and Hyein Jeong, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-Si (KR)
Filed by Samsung Display Co., Ltd., Yongin-Si (KR)
Filed on Jun. 23, 2021, as Appl. No. 17/356,414.
Application 17/356,414 is a continuation of application No. 16/739,048, filed on Jan. 9, 2020, granted, now 11,056,541.
Application 16/739,048 is a continuation in part of application No. 16/134,853, filed on Sep. 18, 2018, granted, now 10,573,692, issued on Feb. 25, 2020.
Application 16/134,853 is a continuation in part of application No. 15/889,028, filed on Feb. 5, 2018, abandoned.
Application 15/889,028 is a continuation of application No. 15/341,223, filed on Nov. 2, 2016, granted, now 9,887,244, issued on Feb. 6, 2018.
Claims priority of application No. 10-2016-0042410 (KR), filed on Apr. 6, 2016.
Prior Publication US 2021/0320154 A1, Oct. 14, 2021
Int. Cl. H10K 59/35 (2023.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/844 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01); H10K 101/00 (2023.01)
CPC H10K 59/35 (2023.02) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02); H10K 50/844 (2023.02); H10K 85/342 (2023.02); H10K 85/615 (2023.02); H10K 85/631 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/8445 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02)] 21 Claims
OG exemplary drawing
 
1. An electronic apparatus comprising:
a substrate;
a pixel defining layer defining a pixel area and a non-pixel area on the substrate;
an organic light-emitting device disposed on the substrate to be surrounded by the pixel defined layer, and comprising at least a first sub-pixel region, a second sub-pixel region, and a third sub-pixel region; and
a thin film encapsulation portion sealing the organic light-emitting device and the pixel defining layer, and comprising at least one organic film,
wherein the organic film comprises a cured product of a composition for forming an organic film, the composition comprising a curable material and an UV absorber dispersed in the curable material, and an amount of the UV absorber is in a range of about 0.1 parts to about 20 parts by weight based on 100 parts by weight of the composition for forming the organic film,
wherein the curable material comprises at least one selected from an acryl-based material, a methacryl-based material, an acrylate-based material, a methacrylate-based material, a vinyl-based material, an epoxy-based material, a urethane-based material, and a cellulose-based material, and
the organic light-emitting device comprises:
a first sub-pixel electrode disposed in the first sub-pixel region, a first sub-pixel intermediate layer disposed on the first sub-pixel electrode;
a second sub-pixel electrode disposed in the second sub-pixel region, a second sub-pixel intermediate layer disposed on the second sub-pixel electrode;
a third sub-pixel electrode disposed in the third sub-pixel region, a third sub-pixel intermediate layer disposed on the third sub-pixel electrode; and
a second electrode
wherein the first sub-pixel intermediate layer comprises a first sub-pixel emission layer, and a first sub-pixel hole transport region between the first sub-pixel electrode and the first sub-pixel emission layer,
the second sub-pixel intermediate layer comprises a second sub-pixel emission layer, and a second sub-pixel hole transport region between the second sub-pixel electrode and the second sub-pixel emission layer, and
the third sub-pixel intermediate layer comprises a third sub-pixel emission layer, and a third sub-pixel hole transport region between the third sub-pixel electrode and the third sub-pixel emission layer,
wherein at least one of the first sub-pixel emission layer, the second sub-pixel emission layer, and the third sub-pixel emission layer includes a first compound represented by Formula 1, and
at least one of the first sub-pixel hole transport region, the second sub-pixel hole transport region, and the third sub-pixel hole transport region includes a diamine compound:

OG Complex Work Unit Chemistry
wherein, in Formulae 1 and 1-1,
rings A1 and A4 are each independently selected from a C5-C60 carbocyclic group and a C1-C30 heterocyclic group,
ring A2 is selected from a C10-C60 carbocyclic group and a C1-C30 heterocyclic group,
ring A3 is selected from a group represented by Formula 1-1,
X1 is selected from N and C-[(L1)a1-(R1)b1], X2 is selected from N and C-[(L2)a2-(R2)b2], X3 is selected from N and C-[(L3)a3-(R3)b3], wherein at least one selected from X1 to X3 is N,
X11 is selected from N-[(L11)a11-(R11)b11], O, S, Se, C(R12)(R13), and Si(R12)(R13),
each of L1 to L6, L11, and L21 to L23 is independently selected from a substituted or unsubstituted C3-C10cycloalkylene group, a substituted or unsubstituted C1-C10heterocycloalkylene group, a substituted or unsubstituted C3-C10cycloalkenylene group, a substituted or unsubstituted C1-C10heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
each of a1 to a6, a11, and a21 to a23 is independently an integer selected from 0 to 5,
each of R1 to R5, R12, R13, and R21 to R23 is independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60arylthio 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, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
R1 and R4 are optionally linked to form a saturated or unsaturated ring, R2 and R4 are optionally linked to form a saturated or unsaturated ring, R3 and R5 are optionally linked to form a saturated or unsaturated ring, R1 and R5 are optionally linked to form a saturated or unsaturated ring,
R11 is selected from a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl 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, substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
each of b1 to b5, and b21 to b23 is independently an integer selected from 0 to 5,
b11 is an integer selected from 1 to 5,
each of n1 to n3 is independently an integer selected from 0 to 4,
wherein at least one of substituents of the substituted C3-C10cycloalkylene group, substituted C1-C10heterocycloalkylene group, substituted C3-C10cycloalkenylene group, substituted C1-C10heterocycloalkenylene group, substituted C6-C60 arylene group, substitute C1-C60heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C1-C10heterocycloalkyl group, substituted C3-C10cycloalkenyl group, substituted C1-C10heterocycloalkenyl group, substitute C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60arylthio group, substituted C1-C60 heteroaryl group, substituted monovalent non-aromatic condense polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, 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 deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkeny group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condense polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
a C3-C10 cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkeny group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60arylthio group, a C1-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 deuterium, —F, —Cl, —Br, —I, a hydroxyl group, cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22-B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryl group substituted with a C1-C60 alkyl group, a C6-C6 aryl group substituted with a C6-C60 aryl group, a terphenyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryl group substituted with a C1-C60 alkyl group, a C1-C60 heteroaryl group substituted with a C6-C60 aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.