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US 12,740,313 B2Granted
Organometallic compound and light-emitting device including the same
AssigneeSamsung Display Co., Ltd.
InventorsHyun-jung Lee, Il-Joon Kang, Soo-byung Ko, Sujin Shin, Junghoon Han
Life of this patent
Estimating the term…
Abstract
An organometallic compound represented by Formula 1 emits deep blue light. A light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device may have excellent or suitable driving voltage, luminescence efficiency, color conversion efficiency, and/or lifespan characteristics: In Formula 1, X1 to X4 are each independently C or N, Y11 is C(Z11) or N, and Y12 is C(Z12) or N.
Claims19
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 emission layer comprises:
- i) a first compound, which is an organometallic compound represented by Formula 1;
- ii) a second compound comprising at least one π electron-deficient nitrogen-containing C1-C60 cyclic group,
- a third compound comprising a group represented by Formula 3,
- a fourth compound to emit delayed fluorescence, or any combination thereof,
- wherein the first compound, the second compound, the third compound, and the fourth compound are different from each other:
- Formulae A4(1) to A4(8)
- wherein, in Formula 1 and Formulae A4(1) to A4(8),
- M is platinum (Pt), palladium (Pd), nickel (Ni), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
- X1 to X4 are each independently C or N,
- Y11 is C(Z11) or N,
- Y12 is C(Z12) or N,
- A1 to A3 are each independently a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
- a group in Formula 1 represented by
- is represented by one of Formulae A4(1) to A4(8),
- L1 to L3 are each independently a single bond, a double bond, *—N(Z21)—*′, *—B(Z21)—*′, *—P(Z21)—*′, *—C(Z21)(Z22)—*′, *—Si(Z21)(Z22)—*′, *—Ge(Z21)(Z22)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)*′, *—S(═O)2—*′, *—C(Z21)═*′, *═C(Z21)—*′, *—C(Z21)═C(Z22)—*′, *—C(═S)—*′, or *≡C C—*′,
- *, *′ and *″ each indicate a binding site to a neighboring atom,
- a1 to a3 are each independently an integer from 0 to 3,
- b48 is an integer from 0 to 8,
- b47 is an integer from 0 to 7,
- R1 to R4, R40, Z11, Z12, Z21, and Z22 are each independently 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), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
- two or more neighboring groups of R1 to R4, R40, Z11, Z12, Z21, and Z22 are optionally bonded to each other to form a C3-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,
- b1 to b3 are each independently an integer from 0 to 10,
- when b1 is 2 or more, two or more R1(s) are identical to or different from each other, when b2 is 2 or more, two or more R2(s) are identical to or different from each other, and when b3 is 2 or more, two or more R3(s) are identical to or different from each other,
- R10a is:
- deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
- a C1-C60 alkylgroup, 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), —P(Q11)(Q12), —C(═O)(Q11), —S(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), —P(═S)(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), —P(Q21)(Q22), —C(═O)(Q21), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), —P(═S)(Q21)(Q22), or any combination thereof;
- or
- —Si(Q31)(Q32)(Q3), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or —P(═S)(Q31)(Q32), and
- 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, and
- wherein, in Formula 3,
- ring CY71 and ring CY72 are each independently a π electron-rich C3-C60 cyclic group or a pyridine group,
- X71 is a single bond or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and
- * indicates a binding site to a neighboring atom in Formula 3.
50 more elements
An organometallic compound represented by Formula 1:
- Formula 1
- Formulae A4(1) to A4(8)
- wherein, in Formula 1 and Formulae A4(1) to A4(8),
- M is platinum (Pt), palladium (Pd), nickel (Ni), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm),
- X1 to X4 are each independently C or N,
- Y11 is C(Z11) or N,
- Y12 is C(Z12) or N,
- A1 to A3 are each independently a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
- a group in Formula 1 represented by
- is represented by one of Formulae A4(1) to A4(8),
- L1 to L3 are each independently a single bond, a double bond, *—N(Z21)—*′, *—B(Z21)—*′, *—P(Z21)—*′, *—C(Z21)(Z22)—*, *—Si(Z21)(Z22)—*, *—Ge(Z21)(Z22)—*, *—S—*′, *—Se—*, *—O—*, *—C(═O)*, *—S(═O)2—*′, *—C(Z21)=*, *═C(Z21)—*, *—C(Z21) ═C(Z22)—*, *—C(═S)—*′, or *≡C C—*′,
- *,*′ and *″ each indicate a binding site to a neighboring atom,
- a1 to a3 are each independently an integer from 0 to 3,
- b48 is an integer from 0 to 8,
- b47 is an integer from 0 to 7,
- R1 to R4, R40, Z11, Z12, Z21, and Z22 are each independently 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), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
- two or more neighboring groups of R1 to R4, R40, Z11, Z12, Z21, and Z22 are optionally bonded to each other to form a C3-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,
- b1 to b3 are each independently an integer from 0 to 10,
- when b1 is 2 or more, two or more R1 (s) are identical to or different from each other, when b2 is 2 or more, two or more R2 (s) are identical to or different from each other, and when b3 is 2 or more, two or more R3 (s) are identical to or different from each other,
- R10a is:
- deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
- a C1-C60 alkylgroup, 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), —P(Q11)(Q12), —C(═O)(Q11), —S(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), —P(═S)(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), —P(Q21)(Q22), —C(═O)(Q21), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), —P(═S)(Q21)(Q22), or any combination thereof;
- or
- —Si(Q31)(Q32)(Q3), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or —P(═S)(Q31)(Q32), and
- 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.