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US 12,101,996 B2Granted
Organometallic compound, light-emitting device including the same, and electronic apparatus
AssigneeSamsung Display Co., Ltd.
InventorsEunyoung Lee, Soobyung Ko, Haejin Kim, Sujin Shin, Eunsoo Ahn, Junghoon Han
Life of this patent
Estimating the term…
Abstract
An organometallic compound represented by Formula 1, a light-emitting device including the same, and an electronic apparatus including the light-emitting device are disclosed. In Formula 1, the substituents are as described in more detail in the specification.
Claims20
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- and
- an interlayer between the first electrode and the second electrode and comprising an emission layer,
- wherein the interlayer comprises at least one organometallic compound represented by Formula 1:
- wherein, in Formula 1,
- M1 is selected from the group consisting of platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
- Y1 to Y3 are each independently selected from the group consisting of a carbon atom (C) and a nitrogen atom (N),
- T1 to T4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), or C(═O),
- when T1 is a chemical bond, Y1 and M1 are directly bonded to each other,
- when T2 is a chemical bond, Y2 and M1 are directly bonded to each other,
- when T3 is a chemical bond, Y3 and M1 are directly bonded to each other,
- when T4 is a chemical bond, C in ring A4 is directly bonded to M1,
- two bonds selected from the group consisting of a bond between M1 and Y1 or T1, a bond between M1 and Y2 or T2, a bond between M1 and Y3 or T3, and a bond between M1 and C in ring A4 or T4 are each a coordinate bond, and the remaining two bonds are each a covalent bond,
- ring A1 to ring A3, ring A11 and ring A12 are each independently selected from the group consisting of a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
- L1 to L3 are each independently selected from the group consisting of a single bond, a double bond, *—N(R4)—*′, *—B(R4)—*′, *—P(R4)—*′, *—C(R4)(R5)—*′, *—Si(R4)(R5)—*′, *—Ge(R4)(R5)—*′, *—S—*′, *—Se*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R4)═*′, *═C(R4)—*′, *—C(R4)═C(R5)—*′, *—C(═S)—*′ and *—C≡C—*′,
- a1 to a3 are each independently an integer from 0 to 3,
- when a1 is 0, ring A1 and ring A2 are not linked to each other,
- when a2 is 0, ring A2 and ring A3 are not linked to each other,
- when a3 is 0, ring A3 and ring A4 are not linked to each other,
- R′, R″, R1 to R5, R11 and R12 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2),
- b1 to b3, b11 and b12 are each independently an integer from 1 to 20,
- two or more neighboring groups from among R1 to R5, R11 and R12 are optionally bonded to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, * and *′ each indicate a binding site to a neighboring atom, and
- R10a is:
- deuterium (—D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof;
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- a C1-C60 alkyl group;
- a C2-C60 alkenyl group;
- a C2-C60 alkynyl group;
- a C1-C60 alkoxy group;
- or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
40 more elements
An organometallic compound represented by Formula 1:
- wherein, in Formula 1,
- M1 is selected from the group consisting of platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
- Y1 to Y3 are each independently selected from the group consisting of a carbon atom (C) and a nitrogen atom (N),
- T1 to T4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), or C(═O),
- when T1 is a chemical bond, Y1 and M1 are directly bonded to each other,
- when T2 is a chemical bond, Y2 and M1 are directly bonded to each other,
- when T3 is a chemical bond, Y3 and M1 are directly bonded to each other,
- when T4 is a chemical bond, C in ring A4 is directly bonded to M1,
- two bonds selected from the group consisting of a bond between M1 and Y1 or T1, a bond between M1 and Y2 or T2, a bond between M1 and Y3 or T3, and a bond between M1 and C in ring A4 or T4 are each a coordinate bond, and the remaining two bonds are each a covalent bond,
- ring A1 to ring A3, ring A11 and ring A12 are each independently selected from the group consisting of a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
- L1 to L3 are each independently selected from the group consisting of a single bond, a double bond, *—N(R4)—*′, *—B(R4)—*′, *—P(R4)—*′, *—C(R4)(R5)—*′, *—Si(R4)(R5)—*′, *—Ge(R4)(R5)—*′, *—S—*′, *—Se*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R4)═*′, *═C(R4)—*′, *—C(R4)═C(R5)—*′, *—C(═S)—*′ and *—C≡C—*′
- a1 to a3 are each independently an integer from 0 to 3,
- when a1 is 0, ring A1 and ring A2 are not linked to each other,
- when a2 is 0, ring A2 and ring A3 are not linked to each other,
- when a3 is 0, ring A3 and ring A4 are not linked to each other,
- R′, R″, R1 to R5, R11 and R12 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2),
- b1 to b3, b11 and b12 are each independently an integer from 1 to 20,
- two or more neighboring groups from among R1 to R5, R11 and R12 are optionally bonded to form a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
- and *′ each indicate a binding site to a neighboring atom, and
- R10a is:
- deuterium (—D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof;
- or
- —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32), and
- wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently:
- hydrogen;
- deuterium;
- —F;
- —Cl;
- —Br;
- —I;
- a hydroxyl group;
- a cyano group;
- a nitro group;
- a C1-C60 alkyl group;
- a C2-C60 alkenyl group;
- a C2-C60 alkynyl group;
- a C1-C60 alkoxy group;
- or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
37 more elements
Dependencies are inferred from the claim text.