Back to results
US 2016/0111663 A1Published application
Organic light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsMyeong-Suk Kim, Sung-Wook Kim, Hwan-Hee Cho, Chang-Woong Chu, Youn-Sun Kim, Naoyuki Ito
Life of this patent
Estimating the term…
Abstract
An organic light-emitting device includes a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; and a hole transport region between the first electrode and the emission layer. The emission layer includes an organometallic compound represented by Formula 1, and the hole transport region includes a first compound represented by Formula 2.
Claims24
An organic light-emitting device comprising
- a first electrode;
- a second electrode facing the first electrode;
- an emission layer between the first electrode and the second electrode;
- a hole transport region between the first electrode and the emission layer,
- wherein the emission layer comprises an organometallic compound represented by Formula 1, and
- the hole transport region comprises a first compound represented by Formula 2:
- M(L1)n1(L2)n2 Formula 1
- wherein, in Formula 1,
- M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rd);
- L1 is a ligand represented by Formula 1A;
- L2 is a ligand represented by Formula 1 B;
- L1 and L2 are different from each other;
- n1 and n2 are each independently 1 or 2, n1+n2=2 or n1+n2=3, when n1 is 2, two L1s are identical to or different from each other, and when n2 is 2, two L2s are identical to or different from each other;
- wherein, in the formulae above,
- CY1 and CY2 are each independently selected from a C5-C60 cyclic group and a C2-C60 heterocyclic group, wherein CY1 and CY2 are linked to each other by a single bond;
- Y1 to Y4 are each independently carbon (C) or nitrogen (N), wherein Y1 and Y2 are linked to each other by a single bond or a double bond, and Y3 and Y4 are linked to each other by a single bond or a double bond;
- CY3 to CY6 are each independently selected from a C5-C40 cyclic group, a C2-C40 heterocyclic group, and Formula 2-1;
- in Formula 2-1, A1 and A2 are each independently selected from a C5-C20 cyclic group and a C2-C20 heterocyclic group;
- X1 is selected from N-(L3)Ib3-Ar2, oxygen atom (O), sulfur atom (S), C(R13)(R14),
- and Si(R15)(R16);
- L1 to L3 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, —N(Q1a)-, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic;
- Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C1-C60 heteroaryl group;
- R1 to R5, and R9 to R16 are each independently selected from a hydrogen atom, a deuterium atom, —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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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 C1-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), and —B(Q6)(Q7),
- R6 to R8 are each independently selected from:
- a C1-C10 alkyl group;
- and
- a C1-C10 alkyl group substituted with at least one selected from a deuterium atom, —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 group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof,
- at least one substituent of the 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-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C1-C60 heteroaryl group, substituted C3-C10 cycloalkylene group, substituted C6-C60 arylene group, substituted C1-C60 heteroarylene group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic, substituted divalent non-aromatic condensed polycyclic group, and substituted divalent non-aromatic condensed heteropolycyclic is selected from:
- a deuterium atom, —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 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;
- 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 atom, —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 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, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17);
- 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, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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, 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 atom, —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 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, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27);
- and
- —N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37),
- wherein Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 are each independently selected from a hydrogen, a deuterium atom, —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 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, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
- Q1a is selected from 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 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,
- a1 and a2 are each independently an integer selected from 0 to 5,
- a3 is an integer selected from 0 to 2,
- a4, b1 to b5, and Ib1 to Ib3 are each independently an integer selected from 0 to 4, and, optionally, when a4 is 2 or greater, a plurality of R5s are condensed to a benzene ring connected to the R5s to form a condensed ring,
- nb1 is 0 or 1,
- nb2 is an integer selected from 0 to 2,
- when at least one selected from a1 to a4 is 2 or greater, at least two selected from R1, R2, R4, and R5 are identical to or different from each other,
- when at least one selected from b1 to b5 is 2 or greater, at least two selected from Ar1 and R9 to R12 are identical to or different from each other,
- when at least one selected from Ib1 to Ib3 is 2 or greater, at least two selected from L1 to L3 are identical to or different from each other, and
- * and *′ are a binding site to M in Formula 1.
42 more elements
Dependencies are inferred from the claim text.