Light-emitting device and electronic apparatus including same
A light-emitting device includes a first compound represented by Formula 1; and a second compound, a third compound, a fourth compound, or any combination thereof, each having a specific formula: emitting device may have excellent driving voltage, current density, high luminescence efficiency, and long lifespan, and may be used in the manufacture of a high quality electronic apparatus.
1 . 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, the interlayer comprising an emission layer,
wherein the interlayer further comprises:
i) a first compound represented by Formula 1; and
ii) a second compound comprising at least one π electron-deficient nitrogen-containing C 1 -C 60 cyclic group, a third compound comprising a group represented by Formula 3, or a fourth compound capable of emitting delayed fluorescent light, or any combination thereof, and
the first compound, the second compound, the third compound, and the fourth compound are different from one another:
wherein, in Formula 1, M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
in Formula 1, X 1 to X 3 are C and X 4 is N,
in Formula 1, i) a bond between X 1 and M is a coordinate bond, and ii) one of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the other two bonds are each a covalent bond,
in Formula 1, ring CY 1 is i) a X 1 -containing 5-membered ring, or ii) a X 1 -containing 5-membered ring condensed with at least one 6-membered ring,
wherein the X 1 -containing 5-membered ring in ring CY 1 in Formula 1 is a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and
the 6-membered ring that is condensed with the X 1 -containing 5-membered ring in ring CY 1 in Formula 1 is a benzene group, a pyridine group, or a pyrimidine group,
in Formula 1, ring CY 2 is a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group,
in Formula 1, X 31 to X 36 and X 41 to X 44 are each independently C,
in Formula 1, X 51 is *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5a )(R 5b )—*, *—Si(R 5a )(R 5b )—*′, *—Ge(R 5a )(R 5b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 5 )=*′, *=C(R 5 )—*′, *—C(R 5a )═C(R 5b )—*′, *—C(═S)—*′, or *—C≡C—*′, and * and *′ each indicate a binding site to an adjacent atom,
in Formula 1, L 1 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formula 1, b1 is an integer from 1 to 5,
in Formula 1, R 1 to R 5 , R 5a , and R 5b are each independently a group represented by Formula 1-1, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , provided that the C 1 -C 60 alkyl group is not substituted with a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
wherein, in Formula 1, c1 is an integer from 0 to 5, a1 and a4 are each independently an integer from 0 to 4, a2 is an integer from 0 to 10, and a3 is an integer from 0 to 6, provided that the sum of a1 to a4 is 1 or greater, and at least one of *-(L 1 ) b1 -(R 1 ) c1 (s) in the number of a1, at least one of R 2 (s) in the number of a2, at least one of R 3 (s) in the number of a3, or at least one of R 4 (s) in the number of a4, or any combination thereof are each independently the group represented by Formula 1-1,
in Formula 1-1, L 7 is a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
in Formula 1-1, b7 is an integer from 1 to 5,
in Formula 1-1, ring CY 7 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formula 1-1, n7 is an integer from 1 to 5,
in Formula 1-1, ring CY 8 is a non-aromatic C 3 -C 60 carbocyclic group or a non-aromatic C 1 -C 60 heterocyclic group,
in Formula 1-1, R 7 and R 8 are each understood by referring to the description of R 1 ,
in Formula 1-1, a7 and a8 are each independently an integer from 0 to 20,
in Formula 3, ring CY 71 and ring CY 72 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
in Formula 3, X 71 is a single bond or a linking group comprising O, S, N, B, C, or Si, or any combination thereof,
in Formula 3, * indicates a binding site to an adjacent atom,
at least two groups represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1 are optionally bound to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
at least two of R 2 (s) in the number of a2 are optionally bound to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
at least two of R 3 (s) in the number of a3 are optionally bound to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
at least two of R 4 (s) in the number of a4 are optionally bound to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
at least two of R 1 to R 5 , R 5a , and R 5b (s) are optionally bound to form a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , and
R 10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), or —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), or —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each independently unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, or any combination thereof, and
the following compounds are excluded from the third compound:
2 . The light-emitting device of claim 1 , wherein the second compound comprises a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, or any combination thereof.
3 . The light-emitting device of claim 1 , wherein the interlayer comprises the second compound.
4 . The light-emitting device of claim 3 , wherein the interlayer further comprises the third compound, or the fourth compound, or any combination thereof.
5 . The light-emitting device of claim 1 , wherein the fourth compound is a compound comprising at least one cyclic group comprising boron (B) and nitrogen (N) as ring forming atoms.
6 . The light-emitting device of claim 5 , wherein the fourth compound is a compound represented by Formula 502, or a compound represented by Formula 503, or any combination thereof:
and
wherein, in Formulae 502 and 503,
ring A 501 to ring A 504 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
Y 505 is O, S, N(R 505 ), B(R 505 ), C(R 505a )(R 505b ), or Si(R 505a )(R 505b ),
Y 506 is O, S, N(R 506 ), B(R 506 ), C(R 506a )(R 506b ), or Si(R 506a )(R 506b ),
Y 507 is O, S, N(R 507 ), B(R 507 ), C(R 507a )(R 507b ), or Si(R 507a )(R 507b ),
Y 508 is O, S, N(R 508 ), B(R 508 ), C(R 508a )(R 508b ), or Si(R 508a )(R 508b ),
Y 51 and Y 52 are each independently B, P(=O), or S(═O),
R 500a , R 500b , R 501 to R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a , and R 508b are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(=O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), and
a501 to a504 are each independently an integer from 0 to 20.
7 . The light-emitting device of claim 1 , wherein the fourth compound comprises a condensed ring in which at least one third ring is condensed with at least one fourth ring,
the third ring is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
the fourth ring is a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
8 . The light-emitting device of claim 1 , wherein the interlayer comprises the fourth compound.
9 . The light-emitting device of claim 1 , wherein the emission layer comprises: i) the first compound; and ii) the second compound, the third compound, or the fourth compound, or any combination thereof, and
the first compound is to emit phosphorescent light or fluorescent light, and
the emission layer is to emit the phosphorescent light or the fluorescent light emitted from the first compound.
10 . The light-emitting device of claim 1 , wherein the first compound is to emit phosphorescent light or fluorescent light, and
the phosphorescent light or the fluorescent light is blue light.
11 . The light-emitting device of claim 1 , wherein, in Formula 1, a4 is an integer from 1 to 4, and one or more of R 4 (s) in the number of a4 are each independently the group represented by Formula 1-1 .
12 . The light-emitting device of claim 1 , wherein, in Formula 1-1, ring CY 7 is i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring and at least one second ring are condensed,
the first ring is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group, and
the second ring is a pyrrole group, a furan group, a thiophene group, a silole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
13 . The light-emitting device of claim 1 , wherein, in Formula 1-1, ring CY 8 is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, or a bicyclo[2.2.2]octane group.
14 . The light-emitting device of claim 1 , wherein, in Formula 1-1, ring CY 8 is a group represented by one of Formulae CY8-1 to CY8-8:
and
wherein, in Formulae CY8-1 to CY8-8, * indicates a binding site to an adjacent atom in Formula 1, and *′ indicates a binding site to L 7 in Formula 1-1.
15 . The light-emitting device of claim 1 , wherein the second compound comprises a compound represented by Formula 2:
wherein, in Formula 2,
L 51 to L 53 are each independently a single bond, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
b51 to b53 are each independently an integer from 1 to 5,
X 54 is N or C(R 54 ), X 55 is N or C(R 55 ), X 56 is N or C(R 56 ), and at least one selected from X 54 to X 56 is N, and
R 51 to R 56 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ).
16 . The light-emitting device of claim 1 , wherein the third compound comprises a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, or a compound represented by Formula 3-5, or any combination thereof:
wherein, in Formulae 3-1 to 3-5,
ring CY 71 to ring CY 74 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
X 82 is a single bond, O, S, N-[(L 82 ) b82 -R 82 ], C(R 82a )(R 82b ), or Si(R 82a )(R 82b ), X 83 is a single bond, O, S, N-[(L 83 ) b83 -R 83 ], C(R 83a )(R 83b ), or Si(R 83a )(R 83b ),
X 84 is O, S, N-[(L 84 ) b84 -R 84 ], C(R 84a )(R 84b ), or Si(R 84a )(R 84b ),
X 85 is C or Si,
L 81 to L 85 are each independently a single bond, *—C(Q 4 )(Q 5 )-*′, *—Si(Q 4 )(Q 5 )-*, a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , or a pyridine group unsubstituted or substituted with at least one R 10a , wherein Q 4 and Q 5 are each understood by referring to the description of Q 1 ,
b81 to b85 are each independently an integer from 1 to 5, and
R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , and R 84b are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(=)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
a71 to a74 are each independently an integer from 0 to 20,
* and *′ each indicate a binding site to an adjacent atom.
17 . An electronic apparatus comprising the light-emitting device of claim 1 .
18 . The electronic apparatus of claim 17 , further comprising a thin-film transistor, wherein the thin-film transistor comprises a source electrode and a drain electrode, and the first electrode of the light-emitting device is electrically connected to one of the source electrode or the drain electrode of the thin-film transistor.
19 . The electronic apparatus of claim 17 , further comprising: a color filter, a color-conversion layer, a touchscreen layer, and/or a polarization layer.