ORGANOMETALLIC COMPOUND, LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING THE LIGHT-EMITTING DEVICE
20230041701 · 2023-02-09
Assignee
Inventors
- Haejin Kim (Yongin-si, KR)
- Soobyung Ko (Yongin-si, KR)
- Sungbum Kim (Yongin-si, KR)
- Sujin Shin (Yongin-si, KR)
- Eunsoo Ahn (Yongin-si, KR)
- Jaesung Lee (Yongin-si, KR)
Cpc classification
C09K2211/185
CHEMISTRY; METALLURGY
H10K30/353
ELECTRICITY
International classification
Abstract
An organometallic compound is represented by Formula 1. A light-emitting device includes a first electrode, a second electrode facing the first electrode, an interlayer disposed between the first electrode and the second electrode and including an emission layer, and at least one organometallic compound represented by Formula 1. An electronic apparatus includes the light-emitting device.
Claims
1. A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; an interlayer disposed between the first electrode and the second electrode and comprising an emission layer; and at least one organometallic compound represented by Formula 1: ##STR00131## wherein in Formula 1, M.sub.1 is 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), or thulium (Tm), X.sub.1 is O, S, N(R.sub.9), or C(R.sub.9)(R.sub.10), Y.sub.1 to Y.sub.4 are each independently a carbon atom (C) or a nitrogen atom (N), Z.sub.11, Z.sub.12, Z.sub.21, Z.sub.22, Z.sub.31, and Z.sub.32 are each independently a carbon atom (C) or a nitrogen atom (N), Z.sub.41 and Z.sub.42 are each independently C(R.sub.6) or N, T.sub.1 to T.sub.4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), or P(R′)(R″), wherein, when T.sub.1 is a chemical bond, Y.sub.1 and M.sub.1 are directly bonded to each other, when T.sub.2 is a chemical bond, Y.sub.2 and M.sub.1 are directly bonded to each other, when T.sub.3 is a chemical bond, Y.sub.3 and M.sub.1 are directly bonded to each other, and when T.sub.4 is a chemical bond, Y.sub.4 and M.sub.1 are directly bonded to each other, two bonds selected from a bond between Y.sub.1 or T.sub.1 and M.sub.1, a bond between Y.sub.2 or T.sub.2 and M.sub.1, a bond between Y.sub.3 or T.sub.3 and M.sub.1, and a bond between Y.sub.4 or T.sub.4 and M.sub.1 are each a coordinate bond, and the other two bonds are each a covalent bond, A.sub.1 to A.sub.4 are each independently a C.sub.5-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, L.sub.1 to L.sub.3 are each independently a single bond, a double bond, *—N(R.sub.7)—*′, *—B(R.sub.7)—*′, *—P(R.sub.7)—*′, *—C(R.sub.7)(R.sub.8)—*′, *—Si(R.sub.7)(R.sub.8)—*′, *—Ge(R.sub.7)(R.sub.8)—*′, *—S—*I, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.7)═*′, *═C(R.sub.7)—*′, *—C(R.sub.7)═C(R.sub.8)—*′, *—C(═S)*′, or *—C≡C—*′, a1 to a3 are each independently an integer from 0 to 3, wherein, when a1 is 0, A.sub.1 and a ring including Y.sub.4 are not linked to each other, when a2 is 0, A.sub.1 and A.sub.2 are not linked to each other, and when a3 is 0, A.sub.2 and A.sub.3 are not linked to each other, and *′ each indicate a binding site to a neighboring atom, and R′, R″, and R.sub.1 to R.sub.10 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), b1 to b4 are each independently an integer from 1 to 20, two neighboring groups selected from R.sub.1 to R.sub.10 are optionally bonded to each other to form a C.sub.5-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, and R.sub.10a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or a combination thereof; a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, or a C.sub.6-C.sub.60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32), wherein Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.
2. The light-emitting device of claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the interlayer further comprises: a hole transport region disposed between the first electrode and the emission layer; and an electron transport region disposed between the emission layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and the electron transport region comprises a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
3. The light-emitting device of claim 1, wherein the interlayer comprises the at least one organometallic compound.
4. The light-emitting device of claim 1, wherein the emission layer comprises the at least one organometallic compound.
5. The light-emitting device of claim 4, wherein the emission layer further comprises a host, and an amount of the at least one organometallic compound is in a range of about 0.01 parts by weight to about 49.99 parts by weight, based on 100 parts by weight of the emission layer.
6. The light-emitting device of claim 4, wherein the emission layer emits blue light having a maximum emission wavelength in a range of about 430 nm to about 490 nm.
7. The light-emitting device of claim 2, wherein the electron transport region comprises a phosphine oxide-containing compound.
8. An electronic apparatus comprising the light-emitting device of claim 1.
9. The electronic apparatus of claim 8, 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 at least one of the source electrode and the drain electrode of the thin-film transistor.
10. The electronic apparatus of claim 8, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.
11. An organometallic compound represented by Formula 1: ##STR00132## wherein in Formula 1, M.sub.1 is 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), or thulium (Tm), X.sub.1 is O, S, N(R.sub.9), or C(R.sub.9)(R.sub.10), Y.sub.1 to Y.sub.4 are each independently a carbon atom (C) or a nitrogen atom (N), Z.sub.11, Z.sub.12, Z.sub.21, Z.sub.22, Z.sub.31, and Z.sub.32 are each independently a carbon atom (C) or a nitrogen atom (N), Z.sub.41 and Z.sub.42 are each independently C(R.sub.6) or N, T.sub.1 to T.sub.4 are each independently a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), or P(R′)(R″), wherein, when T.sub.1 is a chemical bond, Y.sub.1 and M.sub.1 are directly bonded to each other, when T.sub.2 is a chemical bond, Y.sub.2 and M.sub.1 are directly bonded to each other, when T.sub.3 is a chemical bond, Y.sub.3 and M.sub.1 are directly bonded to each other, and when T.sub.4 is a chemical bond, Y.sub.4 and M.sub.1 are directly bonded to each other, two bonds selected from a bond between Y.sub.1 or T.sub.1 and M.sub.1, a bond between Y.sub.2 or T.sub.2 and M.sub.1, a bond between Y.sub.3 or T.sub.3 and M.sub.1, and a bond between Y.sub.4 or T.sub.4 and M.sub.1 are each a coordinate bond, and the other two bonds are each a covalent bond, A.sub.1 to A.sub.4 are each independently a C.sub.5-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, L.sub.1 to L.sub.3 are each independently a single bond, a double bond, *—N(R.sub.7)—*′, *—B(R.sub.7)—*′, *—P(R.sub.7)—*′, *—C(R.sub.7)(R.sub.8)—*′, *—Si(R.sub.7)(R.sub.8)—′, *—Ge(R.sub.7)(R.sub.8)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.7)═*′, *═C(R.sub.7)—*′, *—C(R.sub.7)═C(R.sub.8)—*′, *—C(═S)*′, or *—C≡C—*′, a1 to a3 are each independently an integer from 0 to 3, wherein, when a1 is 0, A.sub.1 and a ring including Y.sub.4 are not linked to each other, when a2 is 0, A.sub.1 and A.sub.2 are not linked to each other, and when a3 is 0, A.sub.2 and A.sub.3 are not linked to each other, * and *′ each indicate a binding site to a neighboring atom, R′, R″, and R.sub.1 to R.sub.10 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), b1 to b4 are each independently an integer from 1 to 20, two neighboring groups selected from R.sub.1 to R.sub.10 are optionally bonded to each other to form a C.sub.5-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, and R.sub.10a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or a combination thereof; a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, or a C.sub.6-C.sub.60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32), wherein Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof.
12. The organometallic compound of claim 11, wherein T.sub.1 to T.sub.4 are each a chemical bond, and at least one of a bond between Y.sub.1 and M.sub.1 and a bond between Y.sub.2 and M.sub.1 are each a coordinate bond.
13. The organometallic compound of claim 11, wherein Y.sub.1, Y.sub.3, and Y.sub.4 are each C, and Y.sub.2 is N, or Y.sub.2 to Y.sub.4 are each C, and Y.sub.1 is N.
14. The organometallic compound of claim 11, wherein Z.sub.11 and Z.sub.12 are each N, or Z.sub.21 and Z.sub.22 are each N.
15. The organometallic compound of claim 11, wherein A.sub.1 to A.sub.4 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cyclohexene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 1,2,4-triazole group, a tetrazole group, a 2,3-dihydrotriazole group, an azasilole group, a diazasilole group, a triazasilole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
16. The organometallic compound of claim 11, wherein A.sub.1 is a group represented by one of Formulae 2A-1 to 2A-33, A.sub.2 is a group represented by one of Formulae 2B-1 to 2B-33, and A.sub.3 is a group represented by one of Formulae 2C-1 to 2C-17: ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## wherein in Formulae 2A-1 to 2A-33, Formulae 2B-1 to 2B-33, and Formulae 2C-1 to 2C-17, Y.sub.21 is N or C(R.sub.21), Y.sub.22 is N or C(R.sub.22), Y.sub.23 is N or C(R.sub.23), Y.sub.24 is N or C(R.sub.24), Y.sub.25 is N or C(R.sub.25), Y.sub.26 is N or C(R.sub.26), Y.sub.27 is N or C(R.sub.27), Y.sub.28 is N or C(R.sub.28), X.sub.21 is N(R.sub.21) or C(R.sub.21)(R.sub.22), R.sub.1a, R.sub.2a, R.sub.21 to R.sub.28, R.sub.21a to R.sub.28a, and R.sub.21b to R.sub.28b are each independently the same as described in connection with R′, R″, and R.sub.1 to R.sub.10 in Formula 1, and indicates a binding site to neighboring T.sub.1, T.sub.2, or T.sub.3, *′ indicates a binding site to neighboring L.sub.1, L.sub.2, or L.sub.3, and *″ indicates a binding site to a neighboring carbon atom.
17. The organometallic compound of claim 11, wherein a1 and a3 are each 1, a2 is 0, L.sub.1 is a single bond, and L.sub.3 is *—O—*′, or a1 and a3 are each 1, a2 is 0, L.sub.1 is *—O—*′, and L.sub.3 is a single bond.
18. The organometallic compound of claim 11, wherein R′, R″, and R.sub.1 to R.sub.10 are each independently: hydrogen, deuterium, —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group; a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with deuterium, —F, —Br, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a alkoxy group, or a combination thereof; a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group; a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group, each substituted with deuterium, —F, —Br, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), —P(═O)(Q.sub.31)(Q.sub.32), or a combination thereof; a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group, each substituted with a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or a combination thereof, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or a combination thereof; a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group, each substituted with a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, or a combination thereof, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or a combination thereof; or —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2), wherein Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.1-C.sub.20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.
19. The organometallic compound of claim 11, wherein the organometallic compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2: ##STR00145## wherein in Formulae 1-1 and 1-2, M.sub.1, A.sub.1 to A.sub.3, X.sub.1, Y.sub.1 to Y.sub.4, Z.sub.11, Z.sub.12, Z.sub.21, Z.sub.22, Z.sub.31, Z.sub.32, Z.sub.41, Z.sub.42, L.sub.1, L.sub.3, R.sub.1 to R.sub.5, and b1 to b4 are each the same as described in Formula 1, A.sub.11 and A.sub.12 are each independently the same as described in connection with A.sub.1 to A.sub.4 in Formula 1, R.sub.11 and R.sub.12 are each independently the same as described in connection with R′, R″, and R.sub.1 to R.sub.10 in Formula 1, and b11 and b12 are each independently the same as described in connection with b1 to b4 in Formula 1.
20. The organometallic compound of claim 11, wherein the organometallic compound represented by Formula 1 is selected from Compounds 1 to 54: ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168##
Description
BRIEF DESCRIPTION OF THE DRAWINGS
[0048] The above and other aspects and features of the disclosure will become more apparent by describing in detail embodiments thereof with reference to the accompanying drawings, in which:
[0049]
[0050]
[0051]
DETAILED DESCRIPTION OF THE EMBODIMENTS
[0052] The disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.
[0053] In the drawings, the sizes, thicknesses, ratios, and dimensions of the elements may be exaggerated for ease of description and for clarity. Like numbers refer to like elements throughout.
[0054] In the description, it will be understood that when an element (or region, layer, part, etc.) is referred to as being “on”, “connected to”, or “coupled to” another element, it can be directly on, connected to, or coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, part, etc.) is described as “covering” another element, it can directly cover the other element, or one or more intervening elements may be present therebetween.
[0055] In the description, when an element is “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without an additional element such as an adhesion element therebetween.
[0056] As used herein, the expressions used in the singular such as “a,” “an,” and “the,” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0057] As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B.” The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”.
[0058] In the specification and the claims, the term “at least one of” is intended to include the meaning of “at least one selected from the group of” for the purpose of its meaning and interpretation. For example, “at least one of A and B” may be understood to mean “A, B, or A and B.” When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.
[0059] It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the disclosure. Similarly, a second element could be termed a first element, without departing from the scope of the disclosure.
[0060] The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation, in addition to the orientation depicted in the drawings. For example, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.
[0061] The terms “about” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the recited value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the recited quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.
[0062] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” and the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or combinations thereof in the disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
[0063] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or excessively formal sense unless clearly defined in the specification.
[0064] An aspect of the disclosure provides an organometallic compound which may be represented by Formula 1:
##STR00002##
[0065] In Formula 1, M.sub.1 may be 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), or thulium (Tm).
[0066] In an embodiment, M.sub.1 may be Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os.
[0067] In an embodiment, M.sub.1 may be Pt, but embodiments are not limited thereto.
[0068] In Formula 1, X.sub.1 may be O, S, N(R.sub.9), or C(R.sub.9)(R.sub.10).
[0069] In an embodiment, X.sub.1 may be O.
[0070] In Formula 1, Y.sub.1 to Y.sub.4 may each independently be a carbon atom (C) or a nitrogen atom (N).
[0071] In an embodiment, Y.sub.1, Y.sub.3, and Y.sub.4 may each be C, and Y.sub.2 may be N, or Y.sub.2 to Y.sub.4 may each be C, and Y.sub.1 may be N.
[0072] In Formula 1, Z.sub.11, Z.sub.12, Z.sub.21, Z.sub.22, Z.sub.31, and Z.sub.32 may each independently be a carbon atom (C) or a nitrogen atom (N).
[0073] In an embodiment, Z.sub.11 and Z.sub.12 may each be N, or Z.sub.21 and Z.sub.22 may each be N.
[0074] In an embodiment, Y.sub.1, Y.sub.3, and Y.sub.4 may each be C, Y.sub.2 may be N, and Z.sub.11 and Z.sub.12 may each be N, or Y.sub.2 to Y.sub.4 may each be C, Y.sub.1 may be N, and Z.sub.21 and Z.sub.22 may each be N.
[0075] In Formula 1, Z.sub.41 and Z.sub.42 may each independently be C(R.sub.6) or N.
[0076] In an embodiment, Z.sub.41 and Z.sub.42 may each be C(R.sub.6).
[0077] In Formula 1, T.sub.1 to T.sub.4 may each independently be a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), or P(R′)(R″), wherein, when T.sub.1 is a chemical bond, Y.sub.1 and M.sub.1 may be directly bonded to each other, when T.sub.2 is a chemical bond, Y.sub.2 and M.sub.1 may be directly bonded to each other, when T.sub.3 is a chemical bond, Y.sub.3 and M.sub.1 may be directly bonded to each other, and when T.sub.4 is a chemical bond, Y.sub.4 and M.sub.1 may be directly bonded to each other, and
[0078] two bonds selected from a bond between Y.sub.1 or T.sub.1 and M.sub.1, a bond between Y.sub.2 or T.sub.2 and M.sub.1, a bond between Y.sub.3 or T.sub.3 and M.sub.1, and a bond between Y.sub.4 or T.sub.4 and M.sub.1 may each be a coordinate bond, and the other two bonds may each be a covalent bond.
[0079] In an embodiment, T.sub.1 to T.sub.4 may each be a chemical bond, and at least one of a bond between Y.sub.1 and M.sub.1 and a bond between Y.sub.2 and M.sub.1 may each be a coordinate bond.
[0080] In Formula 1, A.sub.1 to A.sub.4 may each independently be a C.sub.5-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group.
[0081] In an embodiment, A.sub.1 to A.sub.4 may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cyclohexene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 1,2,4-triazole group, a tetrazole group, a 2,3-dihydrotriazole group, an azasilole group, a diazasilole group, a triazasilole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
[0082] In an embodiment, at least one of A.sub.1 to A.sub.4 may be a 5-membered ring having two or more N(s) or a condensed cyclic group including the 5-membered ring having two or more N(s), and
[0083] at least one of A.sub.1 to A.sub.4 may be a 6-membered ring having one or more N(s) or a condensed cyclic group including the 6-membered ring having one or more N(s).
[0084] In an embodiment, A.sub.1 and A.sub.2 may each independently be an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
[0085] In an embodiment, A.sub.3 and A.sub.4 may each independently be a benzene group, a naphthalene group, an anthracene group, or a phenanthrene group.
[0086] In embodiments, A.sub.1 may be a group represented by one of Formulae 2A-1 to 2A-33, A.sub.2 may be a group represented by one of Formulae 2B-1 to 2B-33, and A.sub.3 may be a group represented by one of Formulae 2C-1 to 2C-17:
##STR00003## ##STR00004## ##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015##
[0087] In Formulae 2A-1 to 2A-33, Formulae 2B-1 to 2B-33, and Formulae 2C-1 to 2C-17,
[0088] Y.sub.21 may be N or C(R.sub.21), Y.sub.22 may be N or C(R.sub.22), Y.sub.23 may be N or C(R.sub.23), Y.sub.24 may be N or C(R.sub.24), Y.sub.25 may be N or C(R.sub.25), Y.sub.26 may be N or C(R.sub.26), Y.sub.27 may be N or C(R.sub.27), and Y.sub.28 may be N or C(R.sub.28),
[0089] X.sub.21 may be N(R.sub.21) or C(R.sub.21)(R.sub.22),
[0090] R.sub.1a, R.sub.2a, R.sub.21 to R.sub.28, R.sub.21a to R.sub.28a, and R.sub.21b to R.sub.28b may each independently be the same as described in connection with R′, R″, and R.sub.1 to R.sub.10 in Formula 1, and
[0091] * indicates a binding site to neighboring T.sub.1, T.sub.2, or T.sub.3, *′ indicates a binding site to neighboring L.sub.1, L.sub.2, or L.sub.3, and *″ indicates a binding site to a neighboring carbon atom.
[0092] In an embodiment, A.sub.1 may be a group represented by Formula 2A-1, 2A-2, or 2A-20.
[0093] In an embodiment, R.sub.1a in Formulae 2A-1 and 2A-2 may not be hydrogen.
[0094] In an embodiment, R.sub.1a in Formulae 2A-1 and 2A-2 may be a C.sub.1-C.sub.20 alkyl group, a C.sub.6-C.sub.20 aryl group, or a C.sub.1-C.sub.20 heteroaryl group;
[0095] a C.sub.1-C.sub.20 alkyl group or a C.sub.6-C.sub.20 aryl group, each substituted with at least one of deuterium, a C.sub.1-C.sub.20 alkyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.1-C.sub.20 alkyl group substituted with at least one deuterium or a C.sub.1-C.sub.20 alkyl group, or a C.sub.6-C.sub.20 aryl group substituted with at least one deuterium or a C.sub.1-C.sub.20 alkyl group.
[0096] In an embodiment, A.sub.2 may be a group represented by Formula 2B-3, 2B-17, or 2B-18.
[0097] In an embodiment, R.sub.2a in Formulae 2B-17 and 2B-18 may not be hydrogen.
[0098] In an embodiment, R.sub.2a in Formulae 2B-17 and 2B-18 may be a C.sub.1-C.sub.20 alkyl group, a C.sub.6-C.sub.20 aryl group, or a C.sub.1-C.sub.20 heteroaryl group;
[0099] a C.sub.1-C.sub.20 alkyl group or a C.sub.6-C.sub.20 aryl group, each substituted with at least one of deuterium, a C.sub.1-C.sub.20 alkyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.1-C.sub.20 alkyl group substituted with at least one deuterium or a C.sub.1-C.sub.20 alkyl group, or a C.sub.6-C.sub.20 aryl group substituted with at least one deuterium or a C.sub.1-C.sub.20 alkyl group.
[0100] In an embodiment, A.sub.3 may be a group represented by Formula 2C-5.
[0101] In an embodiment, in Formula 2C-5, Y.sub.21 may be C(R.sub.21), Y.sub.22 may be C(R.sub.22), and Y.sub.23 may be C(R.sub.23).
[0102] In an embodiment, R.sub.21 to R.sub.23 in Formula 2C-5 may each be hydrogen.
[0103] In an embodiment, A.sub.4 may be a benzene group.
[0104] In Formula 1, L.sub.1 to L.sub.3 may each independently be a single bond, a double bond, *—N(R.sub.7)—*′, *—B(R.sub.7)—*′, *—P(R.sub.7)—*′, *—C(R.sub.7)(R.sub.8)—*′, *—Si(R.sub.7)(R.sub.8)—*′, *—Ge(R.sub.7)(R.sub.8)—*′, *—S—*′, *—Se—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O).sub.2—*′, *—C(R.sub.7)═*′, *═C(R.sub.7)—*′, *—C(R.sub.7)═C(R.sub.8)—*′, *—C(═S)—*′, or *—C≡C—*′, and a1 to a3 may each independently be an integer from 0 to 3, wherein, when a1 is 0, A.sub.1 and a ring including Y.sub.4 may not be linked to each other, when a2 is 0, A.sub.1 and A.sub.2 may not be linked to each other, when a3 is 0, A.sub.2 and A.sub.3 may not be linked to each other.
[0105] In Formula 1, * and *′ may each indicate a binding site to a neighboring atom.
[0106] In an embodiment, at least one of L.sub.1 to L.sub.3 may be *—O—*′.
[0107] In an embodiment, a1 and a3 may each be 1, a2 may be 0, L.sub.1 may be a single bond, and L.sub.3 may be *—O—*′, or a1 and a3 may each be 1, a2 may be 0, L.sub.1 may be *—O—*′, and L.sub.3 may be a single bond.
[0108] In an embodiment, Y.sub.1, Y.sub.3, and Y.sub.4 may each be C, Y.sub.2 may be N, Z.sub.11 and Z.sub.12 may each be N, L.sub.1 may be a single bond, and L.sub.3 may be *—O—*′, or Y.sub.2 to Y.sub.4 may each be C, Y.sub.1 may be N, Z.sub.21 and Z.sub.22 may each be N, L.sub.1 may be *—O—*′, and L.sub.3 may be a single bond.
[0109] In Formula 1, R′, R″, and R.sub.1 to R.sub.10 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 aryloxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.6-C.sub.60 arylthio group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or —P(═O)(Q.sub.1)(Q.sub.2),
[0110] b1 to b4 may each independently be an integer from 1 to 20,
[0111] any two neighboring groups selected from R.sub.1 to R.sub.10 may optionally be bonded to each other to form a C.sub.5-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0112] R.sub.10a may be:
[0113] deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
[0114] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or any combination thereof;
[0115] a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, or a C.sub.6-C.sub.60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or any combination thereof; or
[0116] —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32),
[0117] wherein Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be: hydrogen; deuterium; —F; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C.sub.1-C.sub.60 alkyl group; a C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a C.sub.1-C.sub.60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
[0118] In an embodiment, R′, R″, and R.sub.1 to R.sub.10 may each independently be:
[0119] hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, or a C.sub.1-C.sub.20 alkoxy group;
[0120] a C.sub.1-C.sub.20 alkyl group or a C.sub.1-C.sub.20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a alkoxy group, or any combination thereof;
[0121] a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group;
[0122] a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), —P(═O)(Q.sub.31)(Q.sub.32), or any combination thereof;
[0123] a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group, each substituted with a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, or any combination thereof, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or any combination thereof;
[0124] a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, or a triazinyl group, each substituted with a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, or any combination thereof, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or any combination thereof; or
[0125] —Si(Q.sub.1)(Q.sub.2)(Q.sub.3), —N(Q.sub.1)(Q.sub.2), —B(Q.sub.1)(Q.sub.2), —C(═O)(Q.sub.1), —S(═O).sub.2(Q.sub.1), or P(═O)(Q.sub.1)(Q.sub.2),
[0126] wherein Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be:
[0127] hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.1-C.sub.20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.
[0128] In an embodiment, the organometallic compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:
##STR00016##
[0129] In Formulae 1-1 and 1-2,
[0130] M.sub.1, A.sub.1 to A.sub.4, X.sub.1, Y.sub.1 to Y.sub.4, Z.sub.11, Z.sub.12, Z.sub.21, Z.sub.22, Z.sub.31, Z.sub.32, Z.sub.41, Z.sub.42, L.sub.1, L.sub.3, R.sub.1 to R.sub.5, and b1 to b4 may each be the same as described in Formula 1,
[0131] A.sub.11 and A.sub.12 may each independently be the same as described in connection with A.sub.1 to A.sub.4 in Formula 1,
[0132] R.sub.11 and R.sub.12 may each independently be the same as described in connection with R′, R″, and R.sub.1 to R.sub.10 in Formula 1, and
[0133] b11 and b12 may each independently be the same as described in connection with b1 to b4 in Formula 1.
[0134] In an embodiment, A.sub.11 and A.sub.12 may each be a benzene group.
[0135] In an embodiment, R.sub.11 and R.sub.12 may each be hydrogen.
[0136] In embodiments, the organometallic compound represented by Formula 1 may be represented by Formula 1A or Formula 1B:
##STR00017##
[0137] In Formulae 1A and 1B,
[0138] M.sub.1, X.sub.1, Y.sub.1 to Y.sub.4, Z.sub.11, Z.sub.21, Z.sub.41, Z.sub.42, L.sub.1, and L.sub.3 may each be the same as described in Formula 1,
[0139] Z.sub.13 to Z.sub.16 may each independently be C(R.sub.11) or N, Z.sub.23 to Z.sub.26 may each independently be C(R.sub.12) or N, Z.sub.33 to Z.sub.35 may each independently be C(R.sub.13) or N, and Z.sub.43 to Z.sub.46 may each independently be C(R.sub.14) or N, and
[0140] R.sub.11 to R.sub.14 may each independently be the same as described in connection with R′, R″, and R.sub.1 to R.sub.10 in Formula 1.
[0141] In an embodiment, the organometallic compound represented by Formula 1 may be selected from Compounds 1 to 54, but embodiments are not limited thereto:
##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037##
[0142] The organometallic compound represented by Formula 1 includes a xanthene-, a thioxanthene-, an acridine-, or a dihydroanthracene-based ligand, and thus has a rigid structure in which a central metal is bound by a pentagonal or hexagonal ring structure. This may reduce a vibrational mode of a molecular bond in an excited state, thereby suppressing a decrease in luminescence efficiency due to a loss of non-luminous energy. A conjugate length may be effectively controlled, and thus, a deep blue color wavelength may be realized.
[0143] The organometallic compound represented by Formula 1 may include at least one *—O—*′ as a linker for linking ligands, and thus, for example, a conjugate length of pyridine, which has a large influence on a lowest unoccupied molecular orbital (LUMO) level, may be controlled, thereby shortening an emission wavelength of the organometallic compound.
[0144] The organometallic compound represented by Formula 1 may optionally include a ligand having a carbene structure such as imidazole, and thus may have a stronger bonding force with platinum as the central metal and improved molecular stability, thereby increasing a lifespan of a light-emitting device. For example, when highly reactive hydrogen of imidazole is changed to benzimidazole, the molecular stability may be further improved.
[0145] In the organometallic compound represented by Formula 1, due to the introduction of a substituent having a large steric hindrance to the benzimidazole ligand connected to the central metal, formation of excimers between hosts and dopants, or between the dopants themselves, may be inhibited, and thus, blue light emission of high color purity may be realized.
[0146] The organometallic compound may emit blue light. In an embodiment, the organometallic compound may emit blue light (bottom emission ClE.sub.x,y color coordinates X=0.13, and Y=0.05 to 0.18) having a maximum emission wavelength in a range of about 430 nm to about 490 nm, but embodiments are not limited thereto. Accordingly, the organometallic compound represented by Formula 1 may be useful for the manufacture of a light-emitting device that emits blue light.
[0147] Synthesis methods of the organometallic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Examples provided below.
[0148] A light-emitting device may include at least one organometallic compound represented by Formula 1 between a pair of electrodes of the light-emitting device. In an embodiment, an emission layer of the light-emitting device may include the at least one organometallic compound. The organometallic compound included in the emission layer may be a dopant. In embodiments, the organometallic compound represented by Formula 1 may be a material included in a capping layer located outside a pair of electrodes of a light-emitting device.
[0149] Accordingly, in embodiments, a light-emitting device may include a first electrode, a second electrode facing the first electrode, an interlayer disposed between the first electrode and the second electrode and including an emission layer, and at least one organometallic compound represented by Formula 1.
[0150] In an embodiment, the interlayer may include the at least one organometallic compound.
[0151] The expression “(an interlayer) includes at least one of organometallic compounds” as used herein may include a case in which “(an interlayer) includes identical organometallic compounds represented by Formula 1” and a case in which “(an interlayer) includes two or more different organometallic compounds represented by Formula 1.”
[0152] In an embodiment, the interlayer may include, as the organometallic compound, only Compound 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In embodiments, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in a same layer (for example, both Compound 1 and Compound 2 may be present in an emission layer), or Compound 1 and Compound 2 may be present in different layers (for example, Compound 1 may be present in an emission layer, and Compound 2 may be present in an electron transport region).
[0153] In an embodiment, the first electrode of the light-emitting device may be an anode, the second electrode of the light-emitting device may be a cathode, and the interlayer of the light-emitting device may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof. The electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0154] The term “interlayer” as used herein may refer to a single layer and/or all layers between a first electrode and a second electrode of a light-emitting device. A material included in the “interlayer” is not limited to an organic material.
[0155] In an embodiment, the emission layer may include the at least one organometallic compound.
[0156] In embodiments, the emission layer may include the at least one organometallic compound represented by Formula 1, the emission layer may further include a host, and an amount of the host in the emission layer may be greater than an amount of the at least one organometallic compound in the emission layer.
[0157] In an embodiment, the emission layer may include the at least one organometallic compound represented by Formula 1, the emission layer may further include a host, and an amount of the at least one organometallic compound may be in a range of about 0.01 parts by weight to about 49.99 parts by weight, based on 100 parts by weight of the emission layer.
[0158] In an embodiment, the emission layer may include the at least one organometallic compound represented by Formula 1, and the emission layer may emit blue light having a maximum emission wavelength in a range of about 430 nm to about 490 nm.
[0159] In an embodiment, the electron transport region may include a phosphine oxide-containing compound.
[0160] [Description of
[0161]
[0162] Hereinafter, the structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described with reference to
[0163] [First Electrode 110]
[0164] In
[0165] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be a high-work function material that facilitates injection of holes.
[0166] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide (ZnO), or any combination thereof. In embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof.
[0167] The first electrode 110 may have a structure consisting of a single layer or a structure including multiple layers. In an embodiment, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
[0168] [Interlayer 130]
[0169] The interlayer 130 is located on the first electrode 110. The interlayer 130 may include an emission layer.
[0170] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 150.
[0171] The interlayer 130 may further include, in addition to various organic materials, a metal-containing compound such as an organometallic compound, an inorganic material such as quantum dots, or the like.
[0172] In embodiments, the interlayer 130 may include two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between the two or more emitting units. When the interlayer 130 includes the two or more emitting units and the at least one charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[0173] [Hole Transport Region in Interlayer 130]
[0174] The hole transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a multi-layered structure including layers including different materials.
[0175] The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
[0176] In an embodiment, the hole transport region may have a structure consisting of a layer consisting of different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein for each structure, constituting layers may be stacked from the first electrode 110 in its respective stated order, but the structure of the hole transport region is not limited thereto.
[0177] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
##STR00038##
[0178] In Formulae 201 and 202,
[0179] L.sub.201 to L.sub.204 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0180] L.sub.205 may be *—O—*′, *—S—*′, *—N(Q.sub.201)—*′, a C.sub.1-C.sub.20 alkylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.20 alkenylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, wherein * and *′ each represent a binding site to a neighboring atom,
[0181] xa1 to xa4 may each independently be an integer from 0 to 5,
[0182] xa5 may be an integer from 1 to 10,
[0183] R.sub.201 to R.sub.204 and Q.sub.201 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0184] R.sub.201 and R.sub.202 may optionally be linked to each other via a single bond, a C.sub.1-C.sub.5 alkylene group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.2-C.sub.5 alkenylene group unsubstituted or substituted with at least one R.sub.10a, to form a C.sub.8-C.sub.60 polycyclic group (for example, a carbazole group or the like) unsubstituted or substituted with at least one R.sub.10a (for example, Compound HT16),
[0185] R.sub.203 and R.sub.204 may optionally be linked to each other via a single bond, a C.sub.1-C.sub.5 alkylene group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.2-C.sub.5 alkenylene group unsubstituted or substituted with at least one R.sub.10a, to form a C.sub.8-C.sub.60 polycyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0186] na1 may be an integer from 1 to 4.
[0187] In an embodiment, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY217:
##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045##
[0188] In Formulae CY201 to CY217, R.sub.10b and R.sub.10c may each independently be the same as described in connection with R.sub.10a, ring CY.sub.201 to ring CY.sub.204 may each independently be a C.sub.3-C.sub.20 carbocyclic group or a C.sub.1-C.sub.20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R.sub.10a.
[0189] In an embodiment, ring CY.sub.201 to ring CY.sub.204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
[0190] In embodiments, each of Formulae 201 and 202 may include at least one of groups represented by Formulae CY201 to CY203.
[0191] In embodiments, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.
[0192] In embodiments, in Formula 201, xa1 may be 1, R.sub.201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R.sub.202 may be a group represented by one of Formulae CY204 to CY217.
[0193] In embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203.
[0194] In embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY203, and may include at least one of the groups represented by Formulae CY204 to CY217.
[0195] In embodiments, each of Formulae 201 and 202 may not include a group represented by one of Formulae CY201 to CY217.
[0196] In an embodiment, the hole transport region may include one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:
##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064##
[0197] A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
[0198] The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by an emission layer, and the electron-blocking layer may block the leakage of electrons from an emission layer to a hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron-blocking layer.
[0199] [p-Dopant]
[0200] The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).
[0201] The charge-generation material may be, for example, a p-dopant.
[0202] In an embodiment, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be equal to or less than about −3.5 eV.
[0203] In embodiments, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound containing element EL1 and element EL2, or any combination thereof.
[0204] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
[0205] Examples of the cyano group-containing compound may include HAT-CN, and a compound represented by Formula 221, and the like:
##STR00065##
[0206] In Formula 221,
[0207] R.sub.221 to R.sub.223 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, and
[0208] at least one of R.sub.221 to R.sub.223 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each substituted with a cyano group; —F; —Cl; —Br; —I; a C.sub.1-C.sub.20 alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.
[0209] In the compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.
[0210] Examples of the metal may include an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
[0211] Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
[0212] Examples of the non-metal may include oxygen (O) and a halogen (for example, F, Cl, Br, I, etc.).
[0213] For example, the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, a metal iodide, or the like), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, or the like), a metal telluride, or any combination thereof.
[0214] Examples of the metal oxide may include tungsten oxide (for example, WO, W.sub.2O.sub.3, WO.sub.2, WO.sub.3, W.sub.2O.sub.5, etc.), vanadium oxide (for example, VO, V.sub.2O.sub.3, VO.sub.2, V.sub.2O.sub.5, etc.), molybdenum oxide (MoO, Mo.sub.2O.sub.3, MoO.sub.2, MoO.sub.3, Mo.sub.2O.sub.5, etc.), and rhenium oxide (for example, ReO.sub.3, etc.).
[0215] Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, and a lanthanide metal halide.
[0216] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
[0217] Examples of the alkaline earth metal halide may include BeF.sub.2, MgF.sub.2, CaF.sub.2, SrF.sub.2, BaF.sub.2, BeCl.sub.2, MgCl.sub.2, CaCl.sub.2, SrCl.sub.2, BaCl.sub.2, BeBr.sub.2, MgBr.sub.2, CaBr.sub.2, SrBr.sub.2, BaBr.sub.2, BeI.sub.2, MgI.sub.2, CaI.sub.2, SrI.sub.2, and BaI.sub.2.
[0218] Examples of the transition metal halide may include titanium halide (for example, TiF.sub.4, TiCl.sub.4, TiBr.sub.4, TiI.sub.4, etc.), zirconium halide (for example, ZrF.sub.4, ZrCl.sub.4, ZrBr.sub.4, ZrI.sub.4, etc.), hafnium halide (for example, HfF.sub.4, HfCl.sub.4, HfBr.sub.4, HfI.sub.4, etc.), vanadium halide (for example, VF.sub.3, VCl.sub.3, VBr.sub.3, VI.sub.3, etc.), niobium halide (for example, NbF.sub.3, NbCl.sub.3, NbBr.sub.3, NbI.sub.3, etc.), tantalum halide (for example, TaF.sub.3, TaCl.sub.3, TaBr.sub.3, TaI.sub.3, etc.), chromium halide (for example, CrF.sub.3, CrCl.sub.3, CrBr.sub.3, CrI.sub.3, etc.), molybdenum halide (for example, MoF.sub.3, MoCl.sub.3, MoBr.sub.3, MoI.sub.3, etc.), tungsten halide (for example, WF.sub.3, WCl.sub.3, WBr.sub.3, WI.sub.3, etc.), manganese halide (for example, MnF.sub.2, MnCl.sub.2, MnBr.sub.2, MnI.sub.2, etc.), technetium halide (for example, TcF.sub.2, TcCl.sub.2, TcBr.sub.2, TcI.sub.2, etc.), rhenium halide (for example, ReF.sub.2, ReCl.sub.2, ReBr.sub.2, ReI.sub.2, etc.), iron halide (for example, FeF.sub.2, FeCl.sub.2, FeBr.sub.2, FeI.sub.2, etc.), ruthenium halide (for example, RuF.sub.2, RuCl.sub.2, RuBr.sub.2, RuI.sub.2, etc.), osmium halide (for example, OsF.sub.2, OsCl.sub.2, OsBr.sub.2, OsI.sub.2, etc.), cobalt halide (for example, CoF.sub.2, CoCl.sub.2, CoBr.sub.2, CoI.sub.2, etc.), rhodium halide (for example, RhF.sub.2, RhCl.sub.2, RhBr.sub.2, RhI.sub.2, etc.), iridium halide (for example, IrF.sub.2, IrCl.sub.2, IrBr.sub.2, IrI.sub.2, etc.), nickel halide (for example, NiF.sub.2, NiCl.sub.2, NiBr.sub.2, NiI.sub.2, etc.), palladium halide (for example, PdF.sub.2, PdCl.sub.2, PdBr.sub.2, PdI.sub.2, etc.), platinum halide (for example, PtF.sub.2, PtCl.sub.2, PtBr.sub.2, PtI.sub.2, etc.), copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
[0219] Examples of the post-transition metal halide may include zinc halide (for example, ZnF.sub.2, ZnCl.sub.2, ZnBr.sub.2, ZnI.sub.2, etc.), indium halide (for example, InI.sub.3, etc.), and tin halide (for example, SnI.sub.2, etc.).
[0220] Examples of the lanthanide metal halide may include YbF, YbF.sub.2, YbF.sub.3, SmF.sub.3, YbCl, YbCl.sub.2, YbCl.sub.3, SmCl.sub.3, YbBr, YbBr.sub.2, YbBr.sub.3, SmBr.sub.3, YbI, YbI.sub.2, YbI.sub.3, and SmI.sub.3
[0221] Examples of the metalloid halide may include antimony halide (for example, SbCl.sub.5, etc.).
[0222] Examples of the metal telluride may include an alkali metal telluride (for example, Li.sub.2Te, Na.sub.2Te, K.sub.2Te, Rb.sub.2Te, Cs.sub.2Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe.sub.2, ZrTe.sub.2, HfTe.sub.2, V.sub.2Te.sub.3, Nb.sub.2Te.sub.3, Ta.sub.2Te.sub.3, Cr.sub.2Te.sub.3, Mo.sub.2Te.sub.3, W.sub.2Te.sub.3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu.sub.2Te, CuTe, Ag.sub.2Te, AgTe, Au.sub.2Te, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[0223] [Emission Layer in Interlayer 130]
[0224] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a subpixel. In embodiments, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers may contact each other or may be separated from each other. In embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials may be mixed with each other in a single layer to emit white light.
[0225] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant. The phosphorescent dopant may include the organometallic compound represented by Formula 1.
[0226] An amount of the dopant in the emission layer may be in a range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.
[0227] In embodiments, the emission layer may include a quantum dot.
[0228] The emission layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or as a dopant in the emission layer.
[0229] A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
[0230] [Host in Emission Layer]
[0231] The host may include a compound represented by Formula 301:
[Ar.sub.301].sub.xb11-[(L.sub.301).sub.xb1-R.sub.301].sub.xb21 [Formula 301]
[0232] In Formula 301,
[0233] Ar.sub.301 and L.sub.301 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0234] xb11 may be 1, 2, or 3,
[0235] xb1 may be an integer from 0 to 5,
[0236] R.sub.301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkenyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.2-C.sub.60 alkynyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.301)(Q.sub.302)(Q.sub.303), —N(Q.sub.301)(Q.sub.302), —B(Q.sub.301)(Q.sub.302), —C(═O)(Q.sub.301), —S(═O).sub.2(Q.sub.301), or —P(═O)(Q.sub.301)(Q.sub.302),
[0237] xb21 may be an integer from 1 to 5, and
[0238] Q.sub.301 to Q.sub.303 may each independently be the same as described in connection with Q.sub.1.
[0239] In an embodiment, when xb11 in Formula 301 is 2 or more, two or more of Ar.sub.301(s) may be linked to each other via a single bond.
[0240] In embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
##STR00066##
[0241] In Formulae 301-1 and 301-2,
[0242] ring A.sub.301 to ring A.sub.304 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0243] X.sub.301 may be O, S, N-[(L.sub.304).sub.xb4-R.sub.304], C(R.sub.304)(R.sub.305), or Si(R.sub.304)(R.sub.305),
[0244] xb22 and xb23 may each independently be 0, 1, or 2,
[0245] L.sub.301, xb1, and R.sub.301 may each independently be the same as described in the specification,
[0246] L.sub.302 to L.sub.304 may each independently be the same as described in connection with L.sub.301,
[0247] xb2 to xb4 may each independently be the same as described in connection with xb1, and
[0248] R.sub.302 to R.sub.305 and R.sub.311 to R.sub.314 may each independently be the same as described in connection with R.sub.301.
[0249] In embodiments, the host may include an alkali earth metal complex, a post-transition metal complex, or any combination thereof. In an embodiment, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.
[0250] In embodiments, the host may include one of Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9, 10-bis(naphthalen-2-yl)anthracene (MADN), 9, 10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-Abenzene (TCP), or any combination thereof:
##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094##
[0251] In embodiments, the host may include at least one of a silicon-containing compound (for example, BCPDS used in the following Examples or the like) and a phosphine oxide-containing compound (for example, POPCPA used in the following Examples or the like).
[0252] The host may have various modifications. For example, the host may include only one type of compound or two or more different types of compounds (for example, the host of the following Examples consists of BCPDS and POPCPA).
[0253] [Phosphorescent Dopant]
[0254] The phosphorescent dopant may include the organometallic compound represented by Formula 1.
[0255] The phosphorescent dopant may include at least one transition metal as a center metal.
[0256] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0257] The phosphorescent dopant may be electrically neutral.
[0258] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
##STR00095##
[0259] In Formulae 401 and 402,
[0260] M may be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0261] L.sub.401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein when xc1 is two or more, two or more of L.sub.401 (s) may be identical to or different from each other,
[0262] L.sub.402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, when xc2 is 2 or more, two or more of L.sub.402(s) may be identical to or different from each other,
[0263] X.sub.401 and X.sub.402 may each independently be nitrogen (N) or carbon (C),
[0264] ring A.sub.401 and ring A.sub.402 may each independently be a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group,
[0265] T.sub.401 may be a single bond, *—O—*′, *—C(═O)—*′, *—N(Q.sub.411)—*′, *—C(Q.sub.411)(Q.sub.412)—*′, *—C(Q.sub.411)═C(Q.sub.412)—*′, *—C(Q.sub.411)═*′, or *═C═*′,
[0266] X.sub.403 and X.sub.414 may each independently be a chemical bond (for example, a covalent bond or a coordination bond), O, S, N(Q.sub.413), B(Q.sub.413), P(Q.sub.413), C(Q.sub.413)(Q.sub.414), or Si(Q.sub.413)(Q.sub.414),
[0267] Q.sub.411 to Q.sub.414 may each independently be the same as described in connection with Q.sub.1,
[0268] R.sub.401 and R.sub.402 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.20 alkoxy group unsubstituted or substituted with at least one R.sub.10a, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.401)(Q.sub.402)(Q.sub.403), —N(Q.sub.401)(Q.sub.402), —B(Q.sub.401)(Q.sub.402), —C(═O)(Q.sub.401), —S(═O).sub.2(Q.sub.401), or —P(═O)(Q.sub.401)(Q.sub.402),
[0269] Q.sub.401 to Q.sub.403 may each independently be the same as described in connection with Q.sub.1,
[0270] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0271] * and *′ in Formula 402 each indicate a binding site to M in Formula 401.
[0272] In an embodiment, in Formula 402, X.sub.401 may be nitrogen and X.sub.402 may be carbon, or each of X.sub.401 and X.sub.402 may be nitrogen.
[0273] In embodiments, when xc1 in Formula 402 is 2 or more, two ring A.sub.401(s) in two or more of L.sub.401(s) may be optionally linked to each other via T.sub.402, which is a linking group, and two ring A.sub.402(s) may be optionally linked to each other via T.sub.403, which is a linking group (see Compounds PD1 to PD4 and PD7). T.sub.402 and T.sub.403 may each independently be the same as described in connection with T.sub.401.
[0274] L.sub.402 in Formula 401 may be an organic ligand. In an embodiment, L.sub.402 may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
[0275] The phosphorescent dopant may include, for example, one of compounds PD1 to PD25, or any combination thereof:
##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101##
[0276] [Fluorescent Dopant]
[0277] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0278] For example, the fluorescent dopant may include a compound represented by Formula 501:
##STR00102##
[0279] In Formula 501,
[0280] Ar.sub.501, L.sub.501 to L.sub.503, R.sub.501, and R.sub.502 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0281] xd1 to xd3 may each independently be 0, 1, 2, or 3, and
[0282] xd4 may be 1, 2, 3, 4, 5, or 6.
[0283] In an embodiment, Ar.sub.501 in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, or a pyrene group) in which three or more monocyclic groups are condensed together.
[0284] In embodiments, xd4 in Formula 501 may be 2.
[0285] In an embodiment, the fluorescent dopant may include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107##
[0286] [Delayed Fluorescence Material]
[0287] The emission layer may include a delayed fluorescence material.
[0288] In the specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.
[0289] The delayed fluorescence material included in the emission layer may act as a host or as a dopant depending on the type of other materials included in the emission layer.
[0290] In an embodiment, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be in a range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.
[0291] In an embodiment, the delayed fluorescence material may include a material including at least one electron donor (for example, a 7 electron-rich C.sub.3-C.sub.60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a 7 electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group), and a material including a C.sub.8-C.sub.60 polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).
[0292] Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF9:
##STR00108##
[0293] [Quantum Dot]
[0294] The emission layer may include a quantum dot.
[0295] The term “quantum dot” as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths according to a size of the crystal.
[0296] A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
[0297] The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0298] The wet chemical process is a method which may include mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. When the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled through a process which costs lower, and is easier than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE),
[0299] The quantum dot may include a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group semiconductor compound, a Group IV-VI semiconductor compound, a Group IV element or compound, or any combination thereof.
[0300] Examples of the Group II-VI semiconductor compound may include a binary compound, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; a ternary compound, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.
[0301] Examples of the Group III-V semiconductor compound may include a binary compound such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; a ternary compound such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; a quaternary compound such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. The Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
[0302] Examples of the Group III-VI semiconductor compound may include a binary compound, such as GaS, GaSe, Ga.sub.2Se.sub.3, GaTe, InS, InSe, In.sub.2S.sub.3, In.sub.2Se.sub.3, or InTe; a ternary compound, such as InGaS.sub.3, or InGaSe.sub.3; or any combination thereof.
[0303] Examples of the Group semiconductor compound may include a ternary compound, such as AgInS, AgInS.sub.2, CuInS, CuInS.sub.2, CuGaO.sub.2, AgGaO.sub.2, or AgAlO.sub.2; or any combination thereof.
[0304] Examples of the Group IV-VI semiconductor compound may include a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; a quaternary compound, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.
[0305] The Group IV element or compound may include a single element compound, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.
[0306] Each element included in a multi-element compound such as the binary compound, the ternary compound, and the quaternary compound may be present at a uniform concentration or at a non-uniform concentration in a particle.
[0307] The quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell structure. In an embodiment, when the quantum dot has a core-shell structure, a material included in the core and a material included in the shell may be different from each other.
[0308] The shell of the quantum dot may be a protective layer that prevents chemical degeneration of the core to maintain semiconductor characteristics, and/or may be a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. An interface between the core and the shell may have a concentration gradient in which the concentration of an element in the shell may decrease toward the core.
[0309] Examples of the shell of the quantum dot may include a metal oxide, a metalloid oxide, a non-metal oxide, a semiconductor compound, and any combination thereof. Examples of the metal oxide, the metalloid oxide, or the non-metal oxide may include a binary compound, such as SiO.sub.2, Al.sub.2O.sub.3, TiO.sub.2, ZnO, MnO, Mn.sub.2O.sub.3, Mn.sub.3O.sub.4, CuO, FeO, Fe.sub.2O.sub.3, Fe.sub.3O.sub.4, CoO, Co.sub.3O.sub.4, or NiO; a ternary compound, such as MgAl.sub.2O.sub.4, CoFe.sub.2O.sub.4, NiFe.sub.2O.sub.4, or CoMn.sub.2O.sub.4; or any combination thereof. Examples of the semiconductor compound may include, as described herein, a Group II-VI semiconductor compound; a Group III-V semiconductor compound; a Group III-VI semiconductor compound; a Group I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; or any combination thereof. In an embodiment, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0310] A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be equal to or less than about 45 nm. For example, a FWHM of an emission wavelength spectrum of the quantum dot may be equal to or less than about 40 nm. For example, a FWHM of an emission wavelength spectrum of the quantum dot may be equal to or less than about 30 nm. Within these ranges, color purity or color reproducibility may be increased. Light emitted through the quantum dot may be emitted in all directions, and a viewing angle may be improved.
[0311] The quantum dot may be a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.
[0312] Since the energy band gap may be adjusted by controlling the size of the quantum dot, light having various wavelength bands may be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths may be implemented. In an embodiment, the size of the quantum dot may be selected to emit red light, green light, and/or blue light. The size of the quantum dot may be configured to emit white light by a combination of light of various colors.
[0313] [Electron Transport Region in Interlayer 130]
[0314] The electron transport region may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a multi-layered structure including layers including different materials.
[0315] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0316] In an embodiment, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein, for each structure, constituting layers may be stacked from an emission layer in its respective stated order, but embodiments are not limited thereto.
[0317] In an embodiment, the electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, or the electron transport layer in the electron transport region) may include a metal-free compound including at least one 7 electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group.
[0318] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[Ar.sub.601].sub.xe11-[(L.sub.601).sub.xe1-R.sub.601].sub.xe21 [Formula 601]
[0319] In Formula 601,
[0320] Ar.sub.601 and L.sub.601 may each independently be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a,
[0321] xe11 may be 1, 2, or 3,
[0322] xe1 may be 0, 1, 2, 3, 4, or 5,
[0323] R.sub.601 may be a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, —Si(Q.sub.601)(Q.sub.602)(Q.sub.603), —C(═O)(Q.sub.601), —S(═O).sub.2(Q.sub.601), or —P(═O)(Q.sub.601)(Q.sub.602),
[0324] Q.sub.601 to Q.sub.603 may each independently be the same as described in connection with Q.sub.1,
[0325] xe21 may be 1, 2, 3, 4, or 5, and
[0326] at least one of Ar.sub.601, L.sub.601, and R.sub.601 may each independently be a 7 electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group unsubstituted or substituted with at least one R.sub.10a.
[0327] In an embodiment, when xe11 in Formula 601 is 2 or more, two or more of Ar.sub.601(s) may be linked to each other via a single bond.
[0328] In embodiments, Ar.sub.601 in Formula 601 may be a substituted or unsubstituted anthracene group.
[0329] In embodiments, the electron transport region may include a compound represented by Formula 601-1:
##STR00109##
[0330] In Formula 601-1,
[0331] X.sub.614 may be N or C(R.sub.614), X.sub.615 may be N or C(R.sub.615), X.sub.616 may be N or C(R.sub.616), and at least one of X.sub.614 to X.sub.616 may be N,
[0332] L.sub.611 to L.sub.613 may each independently be the same as described in connection with L.sub.601,
[0333] xe611 to xe613 may each independently be the same as described in connection with xe1,
[0334] R.sub.611 to R.sub.613 may each independently be the same as described in connection with R.sub.601, and
[0335] R.sub.614 to R.sub.616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a.
[0336] In an embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
[0337] The electron transport region may include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1, 10-phenanthroline (Bphen), Alq.sub.3, BAlq, TAZ, NTAZ, or any combination thereof:
##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123##
[0338] In embodiments, the electron transport region may include a phosphine oxide-containing compound (for example, TSPO1 used in the following Examples or the like), but embodiments are not limited thereto. In an embodiment, the phosphine oxide-containing compound may be included in a hole blocking layer in the electron transport region, but embodiments are not limited thereto.
[0339] A thickness of the electron transport region may be in a range of about 100 Å to about 5,000 Å. For example, the thickness of the electron transport region may be in a range of about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, a thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, and a thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 30 Å to about 300 Å. For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole-blocking layer, the electron control layer, and/or the electron transport layer are within these ranges, satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
[0340] The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
[0341] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a L.sub.1 ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth-metal complex may each independently include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
[0342] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (Liq) or Compound ET-D2:
##STR00124##
[0343] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0344] The electron injection layer may have a structure consisting of a layer consisting of a single material, a structure consisting of a layer consisting of different materials, or a multi-layered structure including layers including different materials.
[0345] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0346] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0347] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may include oxides, halides (for example, fluorides, chlorides, bromides, or iodides), or tellurides of the alkali metal, the alkaline earth metal, the rare earth metal, or any combination thereof.
[0348] The alkali metal-containing compound may include alkali metal oxides, such as Li.sub.2O, Cs.sub.2O, or K.sub.2O, alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba.sub.xSr.sub.1−xO (wherein x is a real number satisfying the condition of 0<x<1), Ba.sub.xCa.sub.1−xO (wherein x is a real number satisfying the condition of 0<x<1), or the like. The rare earth metal-containing compound may include YbF.sub.3, ScF.sub.3, Sc.sub.2O.sub.3, Y.sub.2O.sub.3, Ce.sub.2O.sub.3, GdF.sub.3, TbF.sub.3, YbI.sub.3, ScI.sub.3, TbI.sub.3, or any combination thereof. In embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La.sub.2Te.sub.3, Ce.sub.2Te.sub.3, Pr.sub.2Te.sub.3, Nd.sub.2Te.sub.3, Pm.sub.2Te.sub.3, Sm.sub.2Te.sub.3, Eu.sub.2Te.sub.3, Gd.sub.2Te.sub.3, Tb.sub.2Te.sub.3, Dy.sub.2Te.sub.3, Ho.sub.2Te.sub.3, Er.sub.2Te.sub.3, Tm.sub.2Te.sub.3, Yb.sub.2Te.sub.3, and Lu.sub.2Te.sub.3.
[0349] The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include one of ions of the alkali metal, ions of the alkaline earth metal, and ions of the rare earth metal, and a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0350] The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
[0351] In an embodiment, the electron injection layer may consist of an alkali metal-containing compound (for example, alkali metal halide); or an alkali metal-containing compound (for example, alkali metal halide); and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, or the like.
[0352] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
[0353] A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å. For example, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
[0354] [Second Electrode 150]
[0355] The second electrode 150 may be on the interlayer 130 as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as the material for the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low-work function, may be used.
[0356] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0357] The second electrode 150 may have a single-layered structure or a structure including multiple layers.
[0358] [Capping Layer]
[0359] A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. The light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this stated order.
[0360] Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer. Light generated in an emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer.
[0361] The first capping layer and the second capping layer may each increase external luminescence efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
[0362] Each of the first capping layer and the second capping layer may include a material having a refractive index equal to or greater than about 1.6 (at a wavelength of about 589 nm).
[0363] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0364] At least one of the first capping layer and the second capping layer may each independently include carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may each independently be optionally substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0365] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
[0366] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0367] In embodiments, at least one of the first capping layer and the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:
##STR00125##
[0368] [Electronic Apparatus]
[0369] The light-emitting device may be included in various electronic apparatuses. In an embodiment, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, or the like.
[0370] The electronic apparatus (for example, a light-emitting apparatus) may further include, in addition to the light-emitting device, a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and/or the color conversion layer may be located in at least one traveling direction of light emitted from the light-emitting device. In an embodiment, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In an embodiment, the color conversion layer may include quantum dots. The quantum dot may be, for example, a quantum dot as described herein.
[0371] The electronic apparatus may include a first substrate. The first substrate may include subpixels, the color filter may include color filter areas respectively corresponding to the subpixels, and the color conversion layer may include color conversion areas respectively corresponding to the subpixels.
[0372] A pixel-defining film may be located between the subpixels to define each subpixel.
[0373] The color filter may further include color filter areas and light-shielding patterns located among the color filter areas, and the color conversion layer may further include color conversion areas and light-shielding patterns located among the color conversion areas.
[0374] The color filter areas (or the color conversion areas) may include a first area emitting first-color light, a second area emitting second-color light, and/or a third area emitting third-color light, wherein the first-color light, the second-color light, and/or the third-color light may have different maximum emission wavelengths from one another. In an embodiment, the first-color light may be red light, the second-color light may be green light, and the third-color light may be blue light. In an embodiment, the color filter areas (or the color conversion areas) may include quantum dots. The first area may include a red quantum dot, the second area may include a green quantum dot, and the third area may not include a quantum dot. The quantum dot may be the same as described in the specification. The first area, the second area, and/or the third area may each include a scatterer.
[0375] In an embodiment, the light-emitting device may emit first light, the first area may absorb the first light to emit first first-color light, the second area may absorb the first light to emit second first-color light, and the third area may absorb the first light to emit third first-color light. The first first-color light, the second first-color light, and the third first-color light may have different maximum emission wavelengths from one another. For example, the first light may be blue light, the first first-color light may be red light, the second first-color light may be green light, and the third first-color light may be blue light.
[0376] The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.
[0377] The thin-film transistor may further include a gate electrode, a gate insulating film, and the like.
[0378] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0379] The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color conversion layer and/or color filter and the light-emitting device. The sealing portion may allow light from the light-emitting device to be extracted to the outside, and may simultaneously prevent ambient air and/or moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic apparatus may be flexible.
[0380] Various functional layers may be located on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the use of the electronic apparatus. Examples of the functional layer may include a touch screen layer, a polarizing layer, an authentication apparatus, and the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by using biometric information of living matter (for example, fingertips, pupils, etc.).
[0381] The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector.
[0382] The electronic apparatus may be applied to various displays, such as light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and a vessel), projectors, and the like.
[0383] [Description of
[0384]
[0385] The electronic apparatus of
[0386] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0387] A TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0388] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0389] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be located on the active layer 220, and the gate electrode 240 may be located on the gate insulating film 230.
[0390] An interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to provide insulation therebetween.
[0391] The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may contact exposed portions of the source region and the drain region of the active layer 220.
[0392] The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0393] The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may expose a portion of the drain electrode 270 may not completely cover the drain electrode 270, and the first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0394] A pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and an interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. Although not shown in
[0395] The second electrode 150 may be on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0396] The encapsulation portion 300 may be on the capping layer 170. The encapsulation portion 300 may be located on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), or the like), or any combination thereof; or any combination of the inorganic films and the organic films.
[0397]
[0398] The electronic apparatus of
[0399] [Manufacturing Method]
[0400] Respective layers included in the hole transport region, the emission layer, and respective layers included in the electron transport region may be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging (LITI).
[0401] When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10.sup.−8 torr to about 10.sup.−3 torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec, depending on a material to be included in a layer to be formed and the structure of a layer to be formed.
[0402] [Definitions of Terms]
[0403] The term “C.sub.3-C.sub.60 carbocyclic group” as used herein may be a cyclic group consisting only of carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms, and the term “C.sub.1-C.sub.60 heterocyclic group” as used herein may be a cyclic group that has 1 to 60 carbon atoms and further has, in addition to carbon, a heteroatom as ring-forming atoms. The C.sub.3-C.sub.60 carbocyclic group and the C.sub.1-C.sub.60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed with each other. In an embodiment, the C.sub.1-C.sub.60 heterocyclic group may have 3 to 61 ring-forming atoms.
[0404] The term “cyclic group” as used herein may include the C.sub.3-C.sub.60 carbocyclic group and the C.sub.1-C.sub.60 heterocyclic group.
[0405] The term “T.sub.1 electron-rich C.sub.3-C.sub.60 cyclic group” as used herein may be a cyclic group that has 3 to 60 carbon atoms and may not include *—N═*′ as a ring-forming moiety, and the term “T.sub.1 electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group” as used herein may be a heterocyclic group that has 1 to 60 carbon atoms and may include *—N═*′ as a ring-forming moiety.
[0406] In an embodiment,
[0407] the C.sub.3-C.sub.60 carbocyclic group may be a T1 group, or a group in which at least two T1 groups are condensed (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),
[0408] the C.sub.1-C.sub.60 heterocyclic group may be a T2 group, a condensed cyclic group in which at least two T2 groups are condensed with each other, or a condensed cyclic group in which at least one T2 group and at least one T1 group are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0409] the π electron-rich C.sub.3-C.sub.60 cyclic group may be a T1 group, a condensed cyclic group in which at least two T1 groups are condensed with each other, a T3 group, a condensed cyclic group in which at least two T3 groups are condensed with each other, or a condensed cyclic group in which at least one T3 group and at least one T1 group are condensed with each other (for example, the C.sub.3-C.sub.60 carbocyclic group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.),
[0410] the π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group may be a T4 group, a condensed cyclic group in which at least two T4 groups are condensed with each other, a condensed cyclic group in which at least one T4 group and at least one T1 group are condensed with each other, a condensed cyclic group in which at least one T4 group and at least one T3 group are condensed with each other, or a condensed cyclic group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed with one another (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0411] wherein the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene 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,
[0412] the T2 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group,
[0413] the T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and
[0414] the T4 group may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
[0415] The terms “cyclic group,” “C.sub.3-C.sub.60 carbocyclic group,” “C.sub.1-C.sub.60 heterocyclic group,” “π electron-rich C.sub.3-C.sub.60 cyclic group,” or “π electron-deficient nitrogen-containing C.sub.1-C.sub.60 cyclic group” as used herein may each be a group condensed to any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. In an embodiment, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be readily understood by one of ordinary skill in the art according to the structure of a formula including the “benzene group.”
[0416] Examples of the monovalent C.sub.3-C.sub.60 carbocyclic group and the monovalent C.sub.1-C.sub.60 heterocyclic group may include a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and examples of the divalent C.sub.3-C.sub.60 carbocyclic group and the monovalent C.sub.1-C.sub.60 heterocyclic group may include a C.sub.3-C.sub.10 cycloalkylene group, a C.sub.1-C.sub.10 heterocycloalkylene group, a C.sub.3-C.sub.10 cycloalkenylene group, a C.sub.1-C.sub.10 heterocycloalkenylene group, a C.sub.6-C.sub.60 arylene group, a C.sub.1-C.sub.60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
[0417] The term “C.sub.1-C.sub.60 alkyl group” as used herein may be a linear or branched aliphatic hydrocarbon monovalent group that has 1 to 60 carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. The term “C.sub.1-C.sub.60 alkylene group” as used herein may be a divalent group having a same structure as the C.sub.1-C.sub.60 alkyl group.
[0418] The term “C.sub.2-C.sub.60 alkenyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and examples thereof may include an ethenyl group, a propenyl group, and a butenyl group. The term “C.sub.2-C.sub.60 alkenylene group” as used herein may be a divalent group having a same structure as the C.sub.2-C.sub.60 alkenyl group.
[0419] The term “C.sub.2-C.sub.60 alkynyl group” as used herein may be a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C.sub.2-C.sub.60 alkyl group, and examples thereof may include an ethynyl group and a propynyl group. The term “C.sub.2-C.sub.60 alkynylene group” as used herein may be a divalent group having a same structure as the C.sub.2-C.sub.60 alkynyl group.
[0420] The term “C.sub.1-C.sub.60 alkoxy group” as used herein may be a monovalent group represented by —O(A.sub.101) (wherein A.sub.101 is a C.sub.1-C.sub.60 alkyl group), and examples thereof may include a methoxy group, an ethoxy group, and an isopropyloxy group.
[0421] The term “C.sub.3-C.sub.10 cycloalkyl group” as used herein may be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (or bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C.sub.3-C.sub.10 cycloalkylene group” as used herein may be a divalent group having a same structure as the C.sub.3-C.sub.10 cycloalkyl group.
[0422] The term “C.sub.1-C.sub.10 heterocycloalkyl group” as used herein may be a monovalent cyclic group of 1 to 10 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C.sub.1-C.sub.10 heterocycloalkylene group” as used herein may be a divalent group having a same structure as the C.sub.1-C.sub.10 heterocycloalkyl group.
[0423] The term “C.sub.3-C.sub.10 cycloalkenyl group” as used herein may be a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C.sub.3-C.sub.10 cycloalkenylene group” as used herein may be a divalent group having a same structure as the C.sub.3-C.sub.10 cycloalkenyl group.
[0424] The term “C.sub.1-C.sub.10 heterocycloalkenyl group” as used herein may be a monovalent cyclic group that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in the cyclic structure thereof. Examples of the C.sub.1-C.sub.10 heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C.sub.1-C.sub.10 heterocycloalkenylene group” as used herein may be a divalent group having a same structure as the C.sub.1-C.sub.10 heterocycloalkenyl group.
[0425] The term “C.sub.6-C.sub.60 aryl group” as used herein may be a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C.sub.6-C.sub.60 arylene group” as used herein may be a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C.sub.6-C.sub.60 aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. When the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group each include two or more rings, the rings may be condensed with each other.
[0426] The term “C.sub.1-C.sub.60 heteroaryl group” as used herein may be a monovalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C.sub.1-C.sub.60 heteroarylene group” as used herein may be a divalent group having a heterocyclic aromatic system of 1 to 60 carbon atoms, further including, in addition to carbon atoms, at least one heteroatom, as ring-forming atoms. Examples of the C.sub.1-C.sub.60 heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each include two or more rings, the rings may be condensed with each other.
[0427] The term “monovalent non-aromatic condensed polycyclic group” as used herein may be a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, and an indeno anthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed polycyclic group described above.
[0428] The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein may be a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed with each other, at least one heteroatom other than carbon atoms as a ring-forming atom, and no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphtho silolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein may be a divalent group having a same structure as the monovalent non-aromatic condensed heteropolycyclic group described above.
[0429] The term “C.sub.6-C.sub.60 aryloxy group” as used herein may be represented by —O(A.sub.102) (wherein A.sub.102 is a C.sub.6-C.sub.60 aryl group), and the term “C.sub.6-C.sub.60 arylthio group” as used herein may be represented by —S(A.sub.103) (wherein A.sub.103 is a C.sub.6-C.sub.60 aryl group).
[0430] The term “R.sub.10a” as used herein may be:
[0431] deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
[0432] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, or a C.sub.1-C.sub.60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), —P(═O)(Q.sub.11)(Q.sub.12), or any combination thereof;
[0433] a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, or a C.sub.6-C.sub.60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.60 carbocyclic group, a C.sub.1-C.sub.60 heterocyclic group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), —P(═O)(Q.sub.21)(Q.sub.22), or any combination thereof; or
[0434] —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), or —P(═O)(Q.sub.31)(Q.sub.32).
[0435] The term “C.sub.1-C.sub.60 heterocyclic group” as used herein may be a group having a same structure as a C.sub.3-C.sub.60 carbocyclic group, except that as a ring-forming atom at least one heteroatom selected from N, O, Si, P, and S is used in addition to carbon (wherein the number of carbon atoms may be in a range of 1 to 60).
[0436] In the specification, at least one substituent of the substituted C.sub.3-C.sub.60 carbocyclic group, the substituted C.sub.1-C.sub.60 heterocyclic group, the substituted C.sub.3-C.sub.10 cycloalkylene group, the substituted C.sub.1-C.sub.10 heterocycloalkylene group, the substituted C.sub.3-C.sub.10 cycloalkenylene group, the substituted C.sub.1-C.sub.10 heterocycloalkenylene group, the substituted C.sub.6-C.sub.60 arylene group, the substituted C.sub.1-C.sub.60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0437] deuterium, —F, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group;
[0438] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 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 hydrazino group, a hydrazono group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.11)(Q.sub.12)(Q.sub.13), —N(Q.sub.11)(Q.sub.12), —B(Q.sub.11)(Q.sub.12), —C(═O)(Q.sub.11), —S(═O).sub.2(Q.sub.11), and —P(═O)(Q.sub.11)(Q.sub.12);
[0439] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
[0440] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 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, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.21)(Q.sub.22), —B(Q.sub.21)(Q.sub.22), —C(═O)(Q.sub.21), —S(═O).sub.2(Q.sub.21), and —P(═O)(Q.sub.21)(Q.sub.22), and
[0441] —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.31)(Q.sub.32), —B(Q.sub.31)(Q.sub.32), —C(═O)(Q.sub.31), —S(═O).sub.2(Q.sub.31), and —P(═O)(Q.sub.31)(Q.sub.32),
[0442] wherein Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be 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 C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C.sub.1-C.sub.60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C.sub.6-C.sub.60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group.
[0443] Q.sub.1 to Q.sub.3, Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 as used herein may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; C.sub.1-C.sub.60 alkyl group; C.sub.2-C.sub.60 alkenyl group; C.sub.2-C.sub.60 alkynyl group; C.sub.1-C.sub.60 alkoxy group; or a C.sub.3-C.sub.60 carbocyclic group or a C.sub.1-C.sub.60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C.sub.1-C.sub.60 alkyl group, a alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
[0444] The term “heteroatom” as used herein may be any atom other than a carbon atom or a hydrogen atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0445] The term “third-row transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and the like.
[0446] The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “tert-Bu” or “But” as used herein refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.
[0447] The term “biphenyl group” as used herein may be a “phenyl group substituted with a phenyl group.” For example, the “biphenyl group” may be a “substituted phenyl group” having a “C.sub.6-C.sub.60 aryl group” as a substituent.
[0448] The term “terphenyl group” as used herein may be a “phenyl group substituted with a biphenyl group.” For example, the “terphenyl group” may be a “substituted phenyl group” having a “C.sub.6-C.sub.60 aryl group substituted with a C.sub.6-C.sub.60 aryl group” as a substituent.
[0449] The symbols *, *′, and *″ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula.
[0450] Hereinafter, a compound according to embodiments and a light-emitting device according to embodiments will be described in detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an identical molar equivalent of B was used in place of A.
Synthesis Examples
Synthesis Example 1: Synthesis of Compound 3
[0451] ##STR00126##
[0452] 1) Synthesis of Intermediate [A-I]
[0453] A starting material 1-bromo-2-(4-fluorophenoxy)benzene was dissolved in THF (0.15 M), CH.sub.3Li (1.2 eq, 1.6 M in diethyl ether) was added dropwise thereto at−78° C., and the mixture was stirred for 1 hour. (3-methoxyphenyl)(phenyl)methanone dissolved in THF was added dropwise to the mixed solution at −78° C., and the solution was slowly heated to room temperature. After the reaction was terminated using NH.sub.4Cl, the solution was evaporated in a rotary evaporator. Acetic acid was carefully added to the evaporated solution, and fuming HCl was added thereto. The batch was heated to 75° C. and maintained at the temperature for 6 hours. An organic layer was extracted from the mixture by using distilled water and dichloromethane. The organic layer was washed three times with distilled water, dried using magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain Intermediate [A-I] at a yield of 60%.
[0454] 2) Synthesis of Intermediate [A-II]
[0455] Intermediate [A-I] was suspended in HBr (0.5 M) and acetic acid (0.5 M), heated to 120° C., and stirred for 12 hours. The reaction mixture was neutralized with a 0.3 M NaOH aqueous solution, and the resulting solid was filtered. An organic layer was extracted from the filtered solid by using dichloromethane and distilled water. The organic layer was washed three times with distilled water, dried using magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain Intermediate [A-II] at a yield of 75%.
[0456] 3) Synthesis of Intermediate [A-III]
[0457] Intermediate [A-II] (1.5 eq), 2-bromo-4-(tert-butyl)pyridine (1 eq), CuBr (5 mol %), 1-methyl-1H-imidazole (10 mol %), and t-BuOLi (3 eq) were suspended in toluene (0.2 M), heated to 120° C., and stirred for 12 hours. An organic layer was extracted from the reaction mixture by using dichloromethane and distilled water. The organic layer was washed three times with distilled water, dried using magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain Intermediate [A-III] at a yield of 50%.
[0458] 4) Synthesis of Intermediate [A-IV]
[0459] Intermediate [A-III] (1 eq), 1H-benzo[d]imidazole (1.5 eq), and K.sub.3PO.sub.4 (3 eq) were suspended in toluene (0.1M), and stirred at 120° C. for 2 days. An organic layer was extracted from the reaction mixture by using dichloromethane and NH.sub.4Cl. The organic layer was washed three times with distilled water, dried using magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain Intermediate [A-IV] at a yield of 80%.
[0460] 5) Synthesis of Intermediate [A-V]
[0461] Intermediate [A-IV] was dissolved in acetone (0.2 M), iodomethane-D3 (1.2 eq) was added thereto, and the mixture was stirred at room temperature. After completion of the reaction, the solvent was removed therefrom under reduced pressure, and the concentrate was purified by column chromatography to obtain Intermediate [A-V] at a yield of 80%.
[0462] 6) Synthesis of Intermediate [A-VI]
[0463] Intermediate [A-V] was dissolved in a mixed solvent including methanol and distilled water at a ratio of 4:1, and ammonium hexafluorophosphate (2 eq) was added thereto. The resulting solid was stirred at room temperature for 12 hours. The solid was filtered and washed with diethyl ether to obtain Intermediate [A-VI] at a yield of 90%.
[0464] 7) Synthesis of Compound 3
[0465] Intermediate [A-VI], sodium acetate (3.0 eq), and Pt(COD)Cl.sub.2 (1.1 eq) were suspended in a 1,4-dioxane solvent. The reaction mixture was heated to 120° C. and stirred for 12 hours. After completion of the reaction, the solvent was removed therefrom under reduced pressure. Column purification was performed thereon to obtain Compound 3 at a yield of 40%.
Synthesis Example 2: Synthesis of Compound 4
[0466] ##STR00127##
[0467] Compound 4 was obtained in the same manner as used in Synthesis Example 1, except that 1-bromo-2-(4-methoxyphenoxy)benzene and (3-fluorophenyl)(phenyl)methanone were used instead of the starting material 1-bromo-2-(4-fluorophenoxy)benzene and (3-methoxyphenyl)(phenyl)methanone.
Synthesis Example 3: Synthesis of Compound 24
[0468] ##STR00128##
[0469] 1) Synthesis of Intermediate [B-VII]
[0470] Intermediate [B-III], N1-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d10)benzene-1,2-diamine (1.1 eq), Pd.sub.2(dba).sub.3 (5 mol %), SPhos (7.5 mol %), and NaOt-Bu (2 eq) were suspended in toluene (0.1 M), heated to 120° C., and stirred for 12 hours. An organic layer was extracted from the reaction mixture by using dichloromethane and distilled water. The organic layer was washed three times with distilled water, dried using magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain Intermediate [B-VII] at a yield of 70%.
[0471] 2) Synthesis of Intermediate [B-VIII]
[0472] Triethyl orthoformate (0.2 M) and HCl (1 M) were added to Intermediate [B-VII], and the mixture was heated to 80° C. and stirred for 12 hours. The reaction mixture was concentrated under reduced pressure, and purified by column chromatography to obtain Intermediate [B-VIII] at a yield of 90%.
[0473] 3) Synthesis of Intermediate [B-IX]
[0474] Intermediate B-IX was obtained in the same manner as used in synthesis Example 1, except that Intermediate [B-VIII] was used instead of Intermediate [A-V] as a starting material.
[0475] 4) Synthesis of Compound 24
[0476] Compound 24 was obtained in the same manner as used in synthesis Example 1, except that Intermediate [B-IX] was used instead of Intermediate [A-VI] as a starting material.
[0477] .sup.1H NMR and MALDI-TOF of Compounds 3, 4, and 24 synthesized according to Synthesis Examples above are shown in Table 1.
[0478] Synthesis methods for other compounds than the compounds shown in Table 1 may be readily recognized by those skilled in the technical field by referring to the synthesis paths and source materials described above.
TABLE-US-00001 TABLE 1 MALDI-TOF Compound MS[M.sup.+] No. .sup.1H NMR (CDCl.sub.3, 500 MHz) (ppm) found calc. 3 δ 8.04(d, 1H), 7.68~7.58(m, 5H), 809.24 809.10 7.41~7.48(m, 3H), 7.30~7.28(d, 2H), 7.18(s, 1H), 7.06(m, 3H), 6.98(s, 1H), 6.80(d, 1H), 6.75(m, 2H), 6.65(d, 2H), 6.48(m, 1H), 1.28(s, 9H) 4 δ 8.03(d, 1H), 7.65~7.55(m, 3H), 809.24 809.08 7.45~7.50(m, 5H), 7.32(d, 2H), 7.16~7.18(s, 1H), 7.12~7.15(m, 1H), 7.06(m, 2H), 6.95~6.98(s, 1H), 6.77(d, 1H), 6.73(m, 2H), 6.60(d, 2H), 6.55(m, 1H), 1.30(s, 9H) 24 δ 8.20~8.24(d, 2H), 7.70(d, 1H), 1030.02 1030.36 7.38~7.39(m, 2H), 7.26~7.33 (m, 4H), 7.18~7.20(m, 3H) 7.14(m, 2H), 7.10(d, 1H), 6.98(m, 1H), 6.90~6.95(m, 3H), 6.51(s, 1H), 6.45(m, 2H), 5.87(m, 1H), 1.32(s, 9H)
EXAMPLES
Example 1
[0479] As a substrate and an anode, a glass substrate with 15 Ωcm.sup.2 (1,200 Å) ITO thereon, which was manufactured by Corning Inc., was cut to a size of 50 mm×50 mm×0.7 mm, cleaned by sonication with isopropyl alcohol and pure water for 5 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. The resultant glass substrate was loaded onto a vacuum deposition apparatus.
[0480] 2-TNATA was vacuum-deposited on the ITO anode formed on the ITO glass substrate to form a hole injection layer having a thickness of 600 Å, and NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
[0481] Compound 3, which was a dopant, and bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS) and (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), which were a mixed host at the weight ratio of 1:1, were co-deposited on the hole transport layer to form an emission layer having a thickness of 300 Å, wherein the ratio of the dopant to the mixed host was 10%.
[0482] Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq.sub.3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing the manufacture of a light-emitting device.
##STR00129##
Examples 2 and 3 and Comparative Examples 1 and 2
[0483] Light-emitting devices were manufactured in the same manner as in Example 1, except that in forming an emission layer, for use as a dopant, corresponding compounds shown in Table 2 were used instead of Compound 3.
Evaluation Example 1
[0484] The driving voltage, current density, luminance, luminescence efficiency, emission color, and emission wavelength of the light-emitting devices manufactured according to Examples 1 to 3 and Comparative Examples 1 and 2 were measured by using Kethley SMU 236 and a luminance meter PR650, and results thereof are shown in Table 2.
TABLE-US-00002 TABLE 2 Driving Luminescence Emission Device Dopant in the voltage Luminance Efficiency CIE wavelength lifespan Emission layer (V) (cd/m.sup.2) (cd/A) (x, y) (nm) (T.sub.95, h) Example 1 Compound 3 5.30 1000 22.1 (0.135, 0.160) 457 99 Example 2 Compound 4 5.20 1000 22.5 (0.133, 0.165) 459 87 Example 3 Compound 24 5.55 1000 21.4 (0.134, 0.171) 460 88 Comparative Flrpic 6.56 1000 22.9 (0.140, 0.321) 471 4 Example 1 Comparative Compound A 5.65 1000 19.3 (0.199, 0.290) 463 50 Example 2
##STR00130##
[0485] Referring to Table 2, it was confirmed that the light-emitting devices of Examples 1 to 3 had a lower driving voltage, and longer device lifespan than the light-emitting devices of Comparative Examples 1 and 2.
[0486] Light-emitting devices including the organometallic compound represented by Formula 1 may have a low driving voltage, high luminance, high luminescence efficiency and long device lifespan at the same time.
[0487] Embodiments have been disclosed herein, and although terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent by one of ordinary skill in the art, features, characteristics, and/or elements described in connection with an embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of ordinary skill in the art that various changes in form and details may be made without departing from the spirit and scope of the disclosure as set forth in the claims.