Patent Application
20230329085
This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0043645, filed on Apr. 7, 2022, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.
One or more embodiments of the present disclosure relate to an organometallic compound, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device.
From among light-emitting devices, organic light-emitting devices are self-emissive devices that, as compared with other devices of the related art, have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed.
In an example, an organic light-emitting device may have a structure in which a first electrode is on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may recombine in such an emission layer region to produce excitons. These excitons transition from an excited state to the ground state to thereby generate light.
Provided are an organometallic compound having low driving voltage, excellent luminescence efficiency, and long lifespan, a light-emitting device including the same, and an electronic apparatus including the light-emitting device.
Additional aspects of embodiments will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one or more embodiments, provided is a light-emitting device including:
In Formula 1,
According to one or more embodiments, provided is an electronic apparatus including the light-emitting device.
According to one or more embodiments, provided is an electronic device including the light-emitting device.
According to one or more embodiments, provided is an organometallic compound represented by Formula 1.
The above and other aspects and features of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout the specification. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of embodiments. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
According to one or more embodiments, an organometallic compound may be represented by Formula 1:
In an embodiment, M may be platinum (Pt).
X1 to X4 in Formula 1 may each independently be C or N.
In an embodiment, X1 may be C. In an embodiment, X1 in Formula 1 may be C, and C may be carbon of a carbene moiety.
In an embodiment, X2 and X3 may each be C.
In an embodiment, X4 may be N.
In Formula 1, i) a bond between X1 and M may be a coordinate bond (which may also be referred to as a coordinate covalent bond or a dative bond), ii) one selected from a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M may be a coordinate bond (which may also be referred to as a coordinate covalent bond or a dative bond), and the other two may each be a covalent bond.
In an embodiment, a bond between X1 and M is a coordinate bond (which may also be referred to as a coordinate covalent bond or a dative bond), a bond between X2 and M is a covalent bond, a bond between X3 and M is a covalent bond, and a bond between X4 and M is a coordinate bond (which may also be referred to as a coordinate covalent bond or a dative bond).
L1 to L3 in Formula 1 may each independently be a single bond, *—C(R8)(R9)—*′, *—C(R8)=*′, *═C(R8)—*′, *—C(R8)═C(R9)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R8)—*′, *—N(R8)—*′, *—O—*′, *—P(R8)—*′, *—Si(R8)(R9)—*′, *—P(═O)(R8)—*′, *—S—*′, *—S(═O)—*′ *—S(═O)2—*′, or *—Ge(R8)(R9)—*′. * and *′ may each indicate a binding site to a neighboring atom, and R8 and R9 may each be the same as described in the present specification. In this case, L1 to L3 may be identical to or different from each other.
In an embodiment, L1 may be a single bond or *—N(R8)—*′;
n1 to n3 in Formula 1 may each independently be an integer from 1 to 3. N1 in Formula 1 indicates the number of L1(s), wherein, when n1 is 2 or more, two or more L1(s) may be identical to or different from each other. N2 in Formula 1 indicates the number of L2, wherein, when n2 is 2 or more, two or more L2(s) may be identical to or different from each other. N3 in Formula 1 indicates the number of L3, wherein, when n3 is 2 or more, two or more L3(s) may be identical to or different from each other.
In an embodiment, L1 may be a single bond or *—N(R8)—*′; L2 may be *—C(R8)(R9)—*′, *—B(R8)—*′, *—N(R8)—*′, *—O—*′, *—P(R8)—*′, *—Si(R8)(R9)—*′, or *—S—*′; and L3 may be a single bond, *—C(R8)(R9)—*′, *—B(R8)—*′, *—N(R8)—*′, *—O—*′, *—P(R8)—*′, *—Si(R8)(R9)—*′, or *—S—*′.
In an embodiment, n1 to n3 in Formula 1 may each be 1.
Cz in Formula 1 may be a group represented by Formula 1A in the present specification, and b1 may be an integer from 1 to 4.
In Formula 1A, T1 may be a single bond, *—N(Z11)—*′, *—O—*′, *—S—*′, *—C(Z12)(Z13)—*′, or *—Si(Z12)(Z13)—*′. Z11 to Z13 may respectively be the same as those described in the present specification.
In Formula 1A, Ar1 may be a single bond, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In Formula 1A, c1 indicates the number of Ar1(s) in Formula 1A, and may be 0, 1, or 2. In this case, when c1 is 0, a group represented by *—(Ar1)c1—*′ may be a single bond. In an embodiment, c1 may be 0.
In an embodiment, b1 may be 1, 2, or 3, and c1 may be 0.
In an embodiment, b1 may be 2.
Ar1 may be a single bond; or, a cyclopentadiene group, a cyclohepta-1,3-5-triene group, a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphtho indole group, an iso-indole group, a benzoiso-indole group, a naphthoiso-indole 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, a pyrrolo[2,3-b]pyridine 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, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, a 9H-pyrrolo[2,3-b:5,4-b′]dipyridine group, or a naphthoimidazole group, each unsubstituted or substituted with at least one R10a.
In Formula 1 and Formula 1A, ring CY1 to ring CY7 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, wherein ring CY4 may not include a carbene moiety.
The expression “ring CY4 does not include a carbene moiety” may mean that a ring-forming atom of ring CY4 does not include a carbene carbon atom. In this case, the “carbene carbon atom” refers to a (neutral) carbon atom having two unshared valence electrons.
In an embodiment, when X4 is a carbon atom, X4 may not be a carbene carbon atom.
In an embodiment, ring CY4 may not be a 5-membered cyclic carbene group and a 5-membered cyclic carbene group in which at least one 6-membered ring is condensed. The “5-membered cyclic carbene group” refers to a 5-membered ring including a carbene carbon atom as a ring-forming atom, and may refer to, for example, a case where X1 in a group represented by Formula CY1-1 is a carbon atom, but embodiments are not limited thereto. The “5-membered cyclic carbene group in which at least one 6-membered ring is condensed” refers to a cyclic group in which at least one 6-membered ring is condensed together with the 5-membered cyclic carbene group, and may refer to, for example, a case where X1 in a group represented by Formula CY1-4 is a carbon atom, but embodiments are not limited thereto.
In an embodiment, ring CY4 may not be an imidazole group or a benzimidazole group. In an embodiment, ring CY4 may not be an imidazole group including a carbene moiety or a benzimidazole group including a carbene moiety.
In an embodiment, ring CY1 to ring CY7 may each independently be a cyclopentadiene group, a cyclohepta-1,3,5-triene group, a benzene group, a naphthalene group, a fluorene group, a benzofluorene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphtho indole group, an iso-indole group, a benzoiso-indole group, a naphthoiso-indole 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, a pyrrolo[2,3-b]pyridine 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, an azanaphthobenzofuran group, an azanaphthobenzothiophene group, an azabenzocarbazole group, an azabenzofluorene group, an azanaphthobenzosilole group, an azadinaphthofuran group, an azadinaphthothiophene group, an azadibenzocarbazole group, an azadibenzofluorene group, an azadinaphthosilole group, a 9H-pyrrolo[2,3-b:5,4-b′]dipyridine group, or a naphthoimidazole group.
In an embodiment, ring CY1 may be a benzene group, a pyridine group, a pyridazine group, a pyrimidine group, a pyrazine group, a naphthalene group, a quinoline group, an isoquinoline group, a benzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, an imidazole group, a pyrazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a carbazole group, an azacarbazole group, a 9H-pyrrolo[2,3-b:5,4-b′]dipyridine group, or a naphthoimidazole group,
ring CY2 and ring CY3 may each independently be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, a fluorene group, or an azafluorene group, and
ring CY4 may be a benzene group, a pyridine group, a pyridazine group, a pyrimidine group, or a pyrazine group.
In an embodiment, ring CY1 may be a pyridine group, a pyridazine group, a pyrimidine group, a pyrazine group, a benzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, an imidazole group, a pyrazole group, a triazole group, a carbazole group, an azacarbazole group, a 9H-pyrrolo[2,3-b:5,4-b′]dipyridine group, or a naphthoimidazole group.
In an embodiment, ring CY2 and CY3 may each independently be a benzene group, a pyridine group, a pyrimidine group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or an azacarbazole group.
In an embodiment, ring CY4 may be a C1-C60 nitrogen-containing heterocyclic group, and may not include a carbene moiety.
In an embodiment, ring CY4 may be a X4-containing 6-membered ring.
In an embodiment, ring CY4 may be a pyridine group.
In an embodiment, ring CY5 may be a benzene group, a pyridine group, a pyrimidine group, a cyclopentadiene group, or a cyclohepta-1,3-5-triene group.
In an embodiment, ring CY6 and ring CY7 may each independently be a benzene group, a pyridine group, or a pyrimidine group. In an embodiment, ring CY6 and ring CY7 may each independently be a benzene group or a pyridine group.
In Formula 1 and Formula 1A, R1 to R9 and Z11 to Z13 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2).
In Formula 1 and Formula 1A, a1 to a7 may each independently be an integer from 0 to 20.
In Formula 1 and Formula 1A, i) two or more of R1(s) in the number of a1, ii) two or more of R2(s) in the number of a2, iii) two or more of R3(s) in the number of a3, iv) two or more of R4(s) in the number of a4, v) two or more of R5(s) in the number of a5, vi) two or more of R6(s) in the number of a6, vii) two or more of R7(s) in the number of a7, viii) R8 and R9, and ix) Z12 and Z13 may each optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In other words, two or more of R1(s) in the number of a1 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R2(s) in the number of a2 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R3(s) in the number of a3 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R4(s) in the number of a4 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R5(s) in the number of a5 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R6(s) in the number of a6 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
two or more of R7(s) in the number of a7 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a,
R8 and R9 may optionally be bonded to each other to form a C5-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C2-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, and
Z12 and Z13 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
two or more of R1 to R4, R8, and R9 in Formula 1 may optionally be bonded to each other to form a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a.
In an embodiment, a1 to a7 may each independently be an integer from 0 to 10.
In an embodiment, the organometallic compound may be represented by Formula 1-1:
In Formula 1-1, M, X1 to X4, ring CY1 to ring CY3, ring CY5, L1 to L3, n1 to n3, Cz, b1, R1 to R5, a1 to a3, and a5 may each be the same as described in connection with Formula 1, and a4 may be an integer from 0 to 3.
In an embodiment, the organometallic compound may satisfy at least one selected from Condition 1 to Condition 4:
In an embodiment, X1 in Formulae CY1-1 to CY1-28 may be C.
In an embodiment, X1 in Formulae CY1-29 to CY1-50 may be N.
In an embodiment, Y1 in Formulae CY1-1 to CY1-28 may be N(R11), and R11 is the same as described in connection with R1.
In an embodiment, R11 may be a C1-C20 alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, or any combination thereof; or a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each unsubstituted or substituted with deuterium, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, or any combination thereof.
In an embodiment, X2 in Formulae CY2-1 to CY2-23 may be C.
In an embodiment, X3 in Formulae CY3-1 to CY2-23 may be C.
In an embodiment, X4 in Formulae CY4-1 to CY4-6 may be N.
In an embodiment, a group represented by
in Formula 1 and a group represented by
in Formula 1-1 may each independently be a group represented by one selected from Formulae CY4(1) to CY4(32):
In an embodiment, in Formulae CY4(1) to CY4(32),
In an embodiment, a group represented by
in Formula 1 and Formula 1-1 (a group represented by CY(5) in Formulae CY4(1) to CY4(32)) may be a group represented by one selected from Formulae CY5-1 to CY5-18:
In an embodiment, R5b to R5f in Formulae CY5-1 to CY5-18 may each independently be: deuterium, —F, or a cyano group; a C1-C20 alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, or any combination thereof; or a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each unsubstituted or substituted with deuterium, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, or any combination thereof.
In an embodiment, Cz in Formula 1 may be: a carbazolyl group, an azacarbazolyl group, a 9,10-dihydroacridinyl group, a phenoxazinyl group, a phenothiazinyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, or a 5,10-dihydrophenazinyl group; or
In an embodiment, Cz in Formula 1 and Formula 1-1 may be a group represented by Formula 1A-1:
In an embodiment, when T1 in Formula 1A-1 is a single bond, i) one selected from Z61 to Z64 may be N, and each of Z71 to Z74 may not be N, ii) one selected from Z71 to Z74 may be N, and each of Z61 to Z64 may not be N, or iii) each of Z61 to Z64 and Z71 to Z74 may not be N.
In an embodiment, when T1 in Formula 1A-1 is not a single bond, each of Z61 to Z64 and Z71 to Z74 may not be N.
In an embodiment, the organometallic compound represented by Formula 1 may satisfy Condition 4, X4 may be N, Cz may be a group represented by Formula 1A-1, and b1 may be 2.
In an embodiment, Cz in Formula 1 and Formula 1-1 may be selected from groups represented by Formulae 1A-2 to 1A-11:
In an embodiment, R1 to R9 and Z11 to Z13 may each independently be:
In an embodiment, R1 to R9 may each independently be: hydrogen, deuterium, —F, a cyano group, a C1-C10 alkyl group, or a C1-C10 alkoxy group;
In an embodiment, R1 may be: hydrogen, deuterium, —F, or a cyano group; a C1-C20 alkyl group that is unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, or any combination thereof; or a phenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a biphenyl group, a terphenyl group, a C1-C20 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each unsubstituted or substituted with deuterium, —CDs, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, or any combination thereof. Accordingly, compared to another organometallic compound (for example, see Compound CE2 in the present specification), the organometallic compound represented by Formula 1 has a bulky condensed cyclic substituent formed by condensation of three or more monocyclic groups is bonded to a ring including a carbene moiety among rings bonded to a transition metal, and thus, a biased electron density effect is suppressed or reduced such that stability of the organometallic compound represented by Formula 1 may be improved compared to the other organometallic compound, and luminescence efficiency and/or lifespan characteristics of an electronic device (for example, an organic light-emitting device) including the organometallic compound represented by Formula 1 may be further improved.
In an embodiment, Z11 to Z13 may each independently be hydrogen, deuterium, —F, a cyano group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, a hexyl group, a phenyl group, or a biphenyl group.
In an embodiment, the organometallic compound represented by Formula 1 may be selected from Compounds 1 to 144:
may be identical to a group represented by
The organometallic compound represented by Formula 1 may have a bulky condensed cyclic substituent (for example, see a group represented by Formula 1A in the present specification) in which three or more monocyclic groups are condensed to one another. The condensed cyclic substituent is bonded to ring CY4 that does not include a carbene moiety in Formula 1, and thus, may have a strong steric shielding effect toward M in Formula 1. Also, compared to a case where the condensed cyclic substituent is bonded to a ring including a carbene moiety (for example, see Compound CE2 in the present specification), a biased electron density effect is suppressed or reduced such that stability of the organometallic compound represented by Formula 1 may be improved.
Also, in Formula 1A, atoms bonded to N and T1, respectively, among ring-forming atoms of CY6; atoms bonded to N and T1, respectively, among ring-forming atoms of CY7; N; and T1 are linked to each other to form a ring, thereby lowering vibration and improving structural stability of the organometallic compound represented by Formula 1, and thus, the organometallic compound represented by Formula 1 may have high color purity and high stability.
Therefore, an electronic device, for example, an organic light-emitting device, including the organometallic compound represented by Formula 1 may have low driving voltage, excellent luminescence efficiency, long lifespan, and excellent color purity, and thus, may be used in the manufacture of a high-quality electronic apparatus.
Methods of synthesizing the organometallic compound represented by Formula 1 may be easily understood by those of ordinary skill in the art by referring to Synthesis Examples and Examples described herein.
At least one organometallic compound represented by Formula 1 may be used in a light-emitting device (for example, an organic light-emitting device). Therefore, provided is a light-emitting device including: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and the organometallic compound represented by Formula 1 as described in the present specification.
In an embodiment, the interlayer of the light-emitting device may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
In an embodiment, the first electrode of the light-emitting device may be an anode, and the second electrode of the light-emitting device may be a cathode.
In an embodiment, the organometallic compound represented by Formula 1 may be included between the first electrode and the second electrode of the light-emitting device. In an embodiment, the organometallic compound represented by Formula 1 may be included in the interlayer of the light-emitting device, for example, the emission layer of the interlayer.
In an embodiment, the emission layer in the interlayer of the light-emitting device may include a dopant and a host, and the dopant may include the organometallic compound represented by Formula 1. For example, the organometallic compound represented by Formula 1 may serve as a dopant. The emission layer may emit red light, green light, blue light, and/or white light. In an embodiment, the emission layer may emit green light or blue light. The green light may have a maximum emission wavelength of, for example, about 495 nm to about 580 nm, about 500 nm to about 580 nm, about 510 nm to about 580 nm, or about 520 nm to about 580 nm, and the blue light may have a maximum emission wavelength of, for example, about 410 nm to about 500 nm, about 410 nm to about 495 nm, about 420 nm to about 480 nm, or about 430 nm to about 475 nm.
In an embodiment, the interlayer of the light-emitting device may include:
In an embodiment, the following compounds may be excluded from the second compound:
In an embodiment, the emission layer of the light-emitting device may include a dopant and a host,
In an embodiment, the emission layer of the light-emitting device may include a dopant and a host,
In an embodiment, the emission layer may emit phosphorescent or fluorescent light emitted from the first compound. In an embodiment, the phosphorescent or fluorescent light emitted from the first compound may be blue light.
In an embodiment, the second compound may include a compound represented by Formula 2-1, a compound represented by Formula 2-2, a compound represented by Formula 2-3, a compound represented by Formula 2-4, a compound represented by Formula 2-5, or any combination thereof:
In an embodiment, the second compound may be one selected from Compounds H1-1 to H1-24:
In an embodiment, the fourth compound may include a compound represented by Formula 4-11, a compound represented by Formula 4-12, or any combination thereof:
In an embodiment, the sum of c3 and c4, that is, c3+c4, may be 1 or more.
In an embodiment, the fourth compound may include a group represented by Formula 4-1:
In an embodiment, the third compound and the fourth compound may each independently be one selected from Compounds E1 to E32:
In Formula 3, b61 to b63, respectively, indicate numbers of L61 to L63, and may each be an integer from 1 to 5. When b61 is 2 or more, two or more L61 (s) may be identical to or different from each other, when b62 is 2 or more, two or more L62(s) may be identical to or different from each other, and when b63 is 2 or more, two or more L63(s) may be identical to or different from each other. In an embodiment, b61 to b63 may each independently be 1 or 2.
In Formulae 4-11 and 4-12, b92 and b95 may, respectively, indicate numbers of L92 and L95, and may each be an integer from 1 to 5. When b92 is 2 or more, two or more L92(s) may be identical to or different from each other, and when b95 is 2 or more, two or more L95(s) may be identical to or different from each other. In an embodiment, b92 and b95 may each independently be 1 or 2.
L61 to L63 in Formula 3 and L92 and L95 in Formulae 4-11 and 4-12 may each independently be:
In an embodiment, in Formula 3, a bond between L61 and R61, a bond between L62 and R62, a bond between L63 and R63, a bond between two or more L61(s), a bond between two or more L62(s), a bond between two or more L63(s), a bond between L61 and carbon between X64 and X65 in Formula 2, a bond between L62 and carbon between X64 and X66 in Formula 3, and a bond between L63 and carbon between X65 and X66 in Formula 3 may each be a “carbon-carbon single bond”.
In Formula 3, X64 may be N or C(R64), X65 may be N or C(R65), X66 may be N or C(R66), and at least one selected from X64 to X66 may be N. R64 to R66 may each be the same as described in the present specification. In an embodiment, two or three of X64 to X66 may each be N.
R61 to R66, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, and R91 to R95 as used herein may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group that is unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group that is unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group that is unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2). Q1 to Q3 may each be the same as described in the present specification.
In an embodiment, R61 to R66, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R91 to R95 in Formulae 2, 2-1 to 2-5, 3, 4, 4-1, 4-11, and 4-12; and R10a may each independently be:
In an embodiment, in Formula 91,
In an embodiment, R1 to R9, Z11, and Z12 in Formula 1; R61 to R66, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, and R91 to R95 in Formulae 2, 2-1 to 2-5, 3, 4, 4-1, 4-11, and 4-12; and R10a may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one selected from Formulae 9-1 to 9-20 in the present specification, a group represented by one selected from Formulae 10-1 to 10-255 in the present specification, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2) (wherein Q1 to Q3 may each be the same as described in the present specification).
In Formulae 2-1 to 2-5, a71 to a74 respectively indicate numbers of R71 to R74, and may each independently be an integer from 0 to 20. When a71 is 2 or more, two or more R71 (s) may be identical to or different from each other, when a72 is 2 or more, two or more R72(s) may be identical to or different from each other, when a73 is 2 or more, two or more R73(s) may be identical to or different from each other, and when a74 is 2 or more, two or more R74(s) may be identical to or different from each other. A71 to a74 may each independently be an integer from 0 to 8.
In an embodiment, in Formula 3, a group represented by *-(L61)b61-R61 and a group represented by *-(L62)b62-R62 may each not be a phenyl group.
In an embodiment, in Formula 3, a group represented by *-(L61)b61-R61 and a group represented by *-(L62)b62-R62 may be identical to each other.
In an embodiment, in Formula 3, a group represented by *-(L61)b61-R61 and a group represented by *-(L62)b62-R62 may be different from each other.
In an embodiment, b61 and b62 in Formula 3 may be 1, 2, or 3, and L61 and L62 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each unsubstituted or substituted with at least one R10a.
In an embodiment, R61 and R62 in Formula 3 may each independently be a C3-C60 carbocyclic group that is unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group that is unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group that is unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group that is unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3),
In an embodiment,
In an embodiment,
In an embodiment, L81 to L85 in Formulae 2-1 to 2-5 may each independently be:
In an embodiment, a group represented by
in Formulae 2-1 and 2-2 may be a group represented by one selected from Formulae CY71-1(1) to CY71-1(8), and/or
In an embodiment, the light-emitting device may include a capping layer outside the first electrode or outside the second electrode.
In an embodiment, the light-emitting device may further include at least one selected from a first capping layer outside the first electrode and a second capping layer outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one selected from the first capping layer and the second capping layer. Additional details for the first capping layer and/or second capping layer are the same as described in the present specification.
In an embodiment, the light-emitting device may further include:
The expression “(interlayer and/or capping layer) includes an organometallic compound” as used herein may be to mean that the (interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds, each represented by Formula 1.
In an embodiment, the interlayer and/or capping layer may include Compound 1 only as the organometallic compound represented by Formula 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the interlayer may include, as the organometallic compound represented by Formula 1, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, all of Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
The term “interlayer,” as used herein, refers to a single layer and/or all of a plurality of layers between the first electrode and the second electrode of the light-emitting device.
According to one or more embodiments, provided is an electronic apparatus including the light-emitting device. The electronic apparatus may further include a thin-film transistor. In an embodiment, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic apparatus may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. The electronic apparatus may be the same as described in the present specification.
Hereinafter, a structure of the light-emitting device 10 according to an embodiment and a method of manufacturing the light-emitting device 10 will be described in connection with
In
The first electrode 110 may be formed by, for example, depositing and/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 to facilitate injection of holes.
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, the material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the 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.
The first electrode 110 may have a single-layered structure consisting of a single layer, or a multilayer structure including a plurality of layers. In an embodiment, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.
The interlayer 130 is on the first electrode 110. The interlayer 130 includes an emission layer.
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.
The interlayer 130 may further include a metal-containing compound such as an organometallic compound, an inorganic material such as a quantum dot, and/or the like, in addition to various suitable organic materials.
In an embodiment, the interlayer 130 may include, i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two emitting units. When the interlayer 130 includes emitting units and a charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have: i) a single-layered structure consisting of a single layer consisting of a single material; ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials; or iii) a multilayer structure including a plurality of layers including different materials.
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.
In an embodiment, the hole transport region may have a multilayer structure including 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, the layers of each structure being stacked sequentially from the first electrode 110.
The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
In an embodiment, Formulae 201 and 202 may each include at least one selected from groups represented by Formulae CY201 to CY217:
In an embodiment, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In an embodiment, Formulae 201 and 202 may each include at least one selected from groups represented by Formulae CY201 to CY203.
In an embodiment, Formula 201 may include at least one selected from groups represented by Formulae CY201 to CY203 and at least one selected from groups represented by Formulae CY204 to CY217.
In an embodiment, xa1 in Formula 201 may be 1, R201 may be a group represented by one selected from Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by one selected from Formulae CY204 to CY207.
In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY203.
In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY203, and may include at least one selected from groups represented by Formulae CY204 to CY217.
In an embodiment, each of Formulae 201 and 202 may not include groups represented by Formulae CY201 to CY217.
In an embodiment, the hole transport region may include one selected from 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/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), or any combination thereof:
A thickness of the hole transport region may be in a range of about 50 Å to about 10,000 Å, for example, 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, for example, about 100 Å to about 1,000 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, 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, suitable or satisfactory hole-transporting characteristics may be obtained without a substantial increase in driving voltage.
The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance of the wavelength of light emitted by an emission layer, and the electron blocking layer may block or reduce 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.
p-Dopant
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties (e.g., electrically 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).
The charge-generation material may be, for example, a p-dopant.
In an embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be about −3.5 eV or less.
In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including an element EL1 and an element EL2, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like.
In Formula 221,
In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or a combination thereof, and the element EL2 may be a non-metal, a metalloid, or a combination thereof.
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.).
Examples of the metalloid may include silicon (Si), antimony (Sb), and tellurium (Te).
Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).
In an embodiment, examples of the compound containing the element EL1 and the element EL2 may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, and/or a metal iodide), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, and/or a metalloid iodide), a metal telluride, or any combination thereof.
Examples of the metal oxide may include a tungsten oxide (for example, WO, W2O3, WO2, WO3, W2O5, etc.), a vanadium oxide (for example, VO, V2O3, VO2, V2O5, etc.), a molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), and a rhenium oxide (for example, ReO3, etc.).
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.
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.
Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2), SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, Bel2, Mgl2, Cal2, Sr12, and Bal2.
Examples of the transition metal halide may include a titanium halide (for example, TiF4, TiCl4, TiBr4, TiI4, etc.), a zirconium halide (for example, ZrF4, ZrCl4, ZrBr4, Zrl4, etc.), a hafnium halide (for example, HfF4, HfCl4, HfBr4, Hf14, etc.), a vanadium halide (for example, VF3, VCl3, VBr3, VI3, etc.), a niobium halide (for example, NbF3, NbCl3, NbBr3, NbI3, etc.), a tantalum halide (for example, TaF3, TaCl3, TaBr3, TaI3, etc.), a chromium halide (for example, CrF3, CrCl3, CrBr3, CrI3, etc.), a molybdenum halide (for example, MoF3, MoCl3, MoBr3, MoI3, etc.), a tungsten halide (for example, WF3, WCl3, WBr3, WI3, etc.), a manganese halide (for example, MnF2, MnCl2, MnBr2, Mn12, etc.), a technetium halide (for example, TcF2, TcCl2, TcBr2, TcI2, etc.), a rhenium halide (for example, ReF2, ReCl2, ReBr2, ReI2, etc.), an iron halide (for example, FeF2, FeCl2, FeBr2, Fel2, etc.), a ruthenium halide (for example, RuF2, RuC12, RuBr2, RuI2, etc.), an osmium halide (for example, OsF2, OsC12, OsBr2, OsI2, etc.), a cobalt halide (for example, CoF2, COCl2, CoBr2, CoI2, etc.), a rhodium halide (for example, RhF2, RhCl2, RhBr2, RhI2, etc.), an iridium halide (for example, IrF2, IrCl2, IrBr2, Ir12, etc.), a nickel halide (for example, NiF2, NiCl2, NiBr2, NiI2, etc.), a palladium halide (for example, PdF2, PdCl2, PdBr2, PdI2, etc.), a platinum halide (for example, PtF2, PtCl2, PtBr2, PtI2, etc.), a copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), a silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and a gold halide (for example, AuF, AuCl, AuBr, AuI, etc.).
Examples of the post-transition metal halide may include a zinc halide (for example, ZnF2, ZnCl2, ZnBr2, Zn12, etc.), an indium halide (for example, InI3, etc.), and a tin halide (for example, Sn12, etc.).
Examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
Examples of the metalloid halide may include an antimony halide (for example, SbCl5, etc.).
Examples of the metal telluride may include an alkali metal telluride (for example, Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, 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.).
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 sub-pixel. In an embodiment, 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 (e.g., physically contact) each other or may be separated (e.g., spaced apart) from each other to emit white light. In an embodiment, the emission layer may include two or more materials of 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 together with each other in a single layer to emit white light.
The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
An amount of the dopant in the emission layer may be about 0.01 wt % to about 15 wt % based on 100 wt % of the host.
In an embodiment, the emission layer may include a quantum dot.
In an embodiment, 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.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within the range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
The host may be at least one selected from the second compound to the fourth compound.
The host may further include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21 Formula 301
In an embodiment, when xb11 in Formula 301 is 2 or more, two or more Ar301(s) may be linked to each other via a single bond.
In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
In an embodiment, the host may include an alkali earth metal complex, a post-transition metal complex, or a combination thereof. In an embodiment, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or a combination thereof.
In an embodiment, the host may include one selected from Compounds H1 to H128, 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-yl)benzene (TCP), or any combination thereof:
The phosphorescent dopant may be the organometallic compound represented by Formula 1.
The phosphorescent dopant may include at least one transition metal as a central metal.
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.
The phosphorescent dopant may be electrically neutral.
In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
In an embodiment, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) each of X401 and X402 may be nitrogen.
In an embodiment, when xc1 in Formula 402 is 2 or more, two ring A401 in two or more L401 (s) may be optionally linked to each other via T402, which is a linking group, and two ring A402 may optionally be linked to each other via T403, which is a linking group (see Compounds PD1 to PD4 and PD7). T402 and T403 may each independently be the same as described in connection with T401.
L402 in Formula 401 may be an organic ligand. In an embodiment, L402 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, —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.
The phosphorescent dopant may include, for example, one selected from compounds PD1 to PD39, or any combination thereof:
The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
In an embodiment, Ar501 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.
In an embodiment, xd4 in Formula 501 may be 2.
In an embodiment, the fluorescent dopant may include: one selected from Compounds FD1 to FD37; DPVBi; DPAVBi; or any combination thereof:
The emission layer may include a delayed fluorescence material.
In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
The delayed fluorescence material included in the emission layer may act as a host or a dopant depending on the type (or kind) of other materials included in the emission layer.
In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material may be greater than or equal to about 0 eV and less than or equal 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.
In an embodiment, the delayed fluorescence material may include i) a material including at least one electron donor (for example, a π electron-rich C3-C60 cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, or a π electron-deficient nitrogen-containing C1-C60 cyclic group), and ii) a material including a C8-C60 polycyclic group in which two or more cyclic groups are condensed together while sharing boron (B).
Examples of the delayed fluorescence material may include at least one selected from Compounds DF1 to DF14:
The emission layer may include a quantum dot.
In the present specification, a quantum dot refers to a crystal of a semiconductor compound, and may include any suitable material capable of emitting light of various suitable emission wavelengths according to the size of the crystal.
A diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.
The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, and/or any suitable process similar thereto.
According to the wet chemical process, a precursor material is mixed together with an organic solvent to grow a quantum dot particle crystal. As 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 may be controlled through a process which is more easily performed than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), and which has a lower cost.
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 I-III-VI semiconductor compound; a Group IV-VI semiconductor compound; a Group IV element or compound; or any combination thereof.
Examples of the Group II-VI semiconductor compound may include: a binary compound, such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and/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, and/or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combination thereof.
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, and/or InSb; a ternary compound, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound, such as GGaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; or any combination thereof. In an embodiment, the Group III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
Examples of the Group III-VI semiconductor compound may include: a binary compound, such GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and/or InTe; a ternary compound, such as InGaS3, and/or InGaSes; or any combination thereof.
Examples of the Group I-III-VI semiconductor compound may include: a ternary compound, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, and/or AgAlO2; or any combination thereof.
Examples of the Group IV-VI semiconductor compound may include: a binary compound, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and/or the like; a ternary compound, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and/or the like; a quaternary compound, such as SnPbSSe, SnPbSeTe, SnPbSTe, and/or the like; or any combination thereof.
The Group IV element or compound may include: a single element compound, such as Si or Ge; a binary compound, such as SiC and/or SiGe; or any combination thereof.
Each element included in a multi-element compound such as the binary compound, ternary compound and quaternary compound, may exist in a particle with a uniform concentration or non-uniform concentration.
In an embodiment, the quantum dot may have a single structure or a dual core-shell structure. In the case of the quantum dot having a single structure, the concentration of each element included in the corresponding quantum dot may be uniform (e.g., substantially uniform). In an embodiment, the material contained in the core and the material contained in the shell may be different from each other.
The shell of the quantum dot may act as a protective layer to prevent or reduce chemical degeneration of the core to maintain semiconductor characteristics and/or as a charging layer to impart electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The element presented in the interface between the core and the shell of the quantum dot may have a concentration gradient that decreases along a direction toward the center of the quantum dot.
Examples of the material forming the shell of the quantum dot may include an oxide of metal, metalloid, and/or non-metal, a semiconductor compound, or any combination thereof. Examples of the oxide of metal, metalloid, or non-metal may include: a binary compound, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and/or NiO; a ternary compound, such as MgAl2O4, CoFe2O4, NiFe2O4, and/or CoMn2O4; 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 addition, 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.
A full width at half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less, and within these ranges, color purity or color reproducibility may be increased. In addition, because the light emitted through the quantum dot is emitted in all directions (e.g., substantially all directions), the wide viewing angle may be improved.
In addition, 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, and/or a nanoplate particle.
Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having various suitable wavelength bands may be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various suitable wavelengths may be implemented. In an embodiment, the size of the quantum dot may be selected to emit red, green and/or blue light. In addition, the size of the quantum dot may be configured to emit white light by combining light of various suitable colors.
The electron transport region may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.
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.
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, the constituting layers of each structure being sequentially stacked from an emission layer.
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 π electron-deficient nitrogen-containing C1-C60 cyclic group.
In an embodiment, the electron transport region may include at least one selected from the third compound and the fourth compound.
In an embodiment, the electron transport region may include a compound represented by Formula 601.
[Ar601]xe11-[(L601)xe1-R601]xe21 Formula 601
In Formula 601,
In an embodiment, when xe11 in Formula 601 is 2 or more, two or more Ar601(s) may be linked to each other via a single bond.
In an embodiment, Ar601 in Formula 601 may be a substituted or unsubstituted anthracene group.
In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
In an embodiment, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.
The electron transport region may include one selected from Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
A thickness of the electron transport region may be about 100 Å to about 5,000 Å, for example, 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, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may each independently be from about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport region are within these ranges, suitable or satisfactory electron transporting characteristics may be obtained without a substantial increase in driving voltage.
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.
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 Li 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 alkaline earth-metal complex may 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.
In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) and/or ET-D2:
The electron transport region may include an electron injection layer to facilitate the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 150.
The electron injection layer may have: i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of a single layer consisting of a plurality of different materials, or iii) a multilayer structure including a plurality of layers including different materials.
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.
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.
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, and the rare earth metal, or any combination thereof.
The alkali metal-containing compound may include alkali metal oxides, such as Li2O, Cs2O, and/or K2O, alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI, or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, BaxSr1-xO (x is a real number satisfying the condition of 0<x<1), BaxCa1-xO (x is a real number satisfying the condition of 0<x<1), and/or the like. The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal-containing compound may include 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, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include i) one selected from an ion of the alkali metal, the alkaline earth metal, and the rare earth metal and ii), as a ligand bonded to the metal ion, for example, a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
The electron injection layer may include (e.g., 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 an embodiment, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).
In an embodiment, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, an alkali metal halide), ii) a) an alkali metal-containing compound (for example, an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, a LiF:Yb co-deposited layer, and/or the like.
When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth-metal complex, rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, suitable or satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be on the interlayer 130 having such a structure. 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.
In an embodiment, 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.
The second electrode 150 may have a single-layered structure or a multilayer structure including two or more layers.
A first capping layer may be outside the first electrode 110, and/or a second capping layer may be outside the second electrode 150. In more detail, 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 sequentially 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 sequentially 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 sequentially stacked in this stated order.
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 is a semi-transmissive electrode or a transmissive electrode, and the first capping layer or 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 is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.
The first capping layer and the second capping layer may increase external emission efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.
Each of the first capping layer and second capping layer may include a material having a refractive index (at a wavelength of 589 nm) of 1.6 or more.
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 an organic-inorganic composite capping layer including an organic material and an inorganic material.
At least one selected from 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 be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In an embodiment, at least one selected from 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.
In an embodiment, at least one selected from the first capping layer and the second capping layer may each independently include one selected from Compounds HT28 to HT33, one selected from Compounds CP1 to CP6, β-NPB, or any combination thereof:
The organometallic compound represented by Formula 1 may be included in various suitable films. According to one or more embodiments, a film including the organometallic compound represented by Formula 1 may be provided. The film may be, for example, an optical member (or a light control member) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, and/or like), a light-blocking member (for example, a light reflective layer, a light absorbing layer, and/or the like), a protective member (for example, an insulating layer, a dielectric layer, and/or the like).
The light-emitting device may be included in various suitable electronic apparatuses. In an embodiment, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.
The electronic apparatus (for example, light-emitting apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and/or the color conversion layer may be 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 in the present specification.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of subpixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the subpixel areas, and the color conversion layer may include a plurality of color conversion areas respectively corresponding to the subpixel areas.
A pixel-defining layer may be among the subpixel areas to define each of the subpixel areas.
The color filter may further include a plurality of color filter areas and light-shielding patterns among the color filter areas, and the color conversion layer may include a plurality of color conversion areas and light-shielding patterns among the color conversion areas.
The color filter areas (or the color conversion areas) may include a first area that emits a first color light, a second area that emits a second color light, and/or a third area that emits a third color light, and 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. In more detail, 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 present specification. The first area, the second area, and/or the third area may each further include a scatterer (e.g., a light scatterer).
In an embodiment, the light-emitting device may emit a first light, the first area may absorb the first light to emit a first first-color light, the second area may absorb the first light to emit a second first-color light, and the third area may absorb the first light to emit a third first-color light. In this regard, the first first-color light, the second first-color light, and the third first-color light may each have different maximum emission wavelengths. In more detail, 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.
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 activation layer, wherein any one selected from the source electrode and the drain electrode may be electrically connected to any one selected from the first electrode and the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, etc.
The activation layer may include crystalline silicon, amorphous silicon, organic semiconductor, oxide semiconductor, or the like.
The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be between the color filter and/or the color-conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, while concurrently (e.g., simultaneously) preventing or reducing penetration of ambient air and/or moisture into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer 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.
Various suitable functional layers may be additionally on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the intended use of the electronic apparatus. The functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, and/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 a living body (for example, fingertips, pupils, etc.).
The authentication apparatus may further include, in addition to the light-emitting device, a biometric information collector.
The electronic apparatus may be applied to various suitable displays, light sources, lighting, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic diaries, 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, and/or endoscope displays), fish finders, various suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like.
The light-emitting device may be included in various suitable electronic devices.
In an embodiment, an electronic device including the light-emitting device may be one selected from a flat panel display, a curved display, a computer monitor, a medical monitor, a television (TV), a billboard, indoor or outdoor illuminations and/or signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a cell phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3D displays, virtual or augmented reality displays, vehicles, a video wall including multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a signage.
Because the light-emitting device has excellent luminescence efficiency, long lifespan, and the like, the electronic device including the light-emitting device may have characteristics of high luminance, high resolution, and low power consumption.
The light-emitting apparatus of
The substrate 100 may be a flexible substrate, a glass substrate, and/or a metal substrate. A buffer layer 210 may be formed on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
A TFT may be on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The activation 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.
A gate insulating film 230 for insulating the activation layer 220 from the gate electrode 240 may be on the activation layer 220, and the gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 is on the gate electrode 240. The interlayer insulating film 250 may be placed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be in contact (e.g., physical contact) with the exposed portions of the source region and the drain region of the activation layer 220.
The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a 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.
The first electrode 110 may be formed on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a portion of the drain electrode 270, and the first electrode 110 is connected to the exposed portion of the drain electrode 270.
A pixel-defining layer 290 containing an insulating material may be on the first electrode 110. The pixel-defining layer 290 exposes 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. In some embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel-defining layer 290 in the form of a common layer.
The second electrode 150 may be on the interlayer 130, and a capping layer 170 may be additionally on the second electrode 150. The capping layer 170 may cover the second electrode 150.
The encapsulation portion 300 may be on the capping layer 170. The encapsulation portion 300 may be 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, and/or the like), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), and/or the like), or a combination thereof; or a combination of the inorganic film and the organic film.
The light-emitting apparatus of
The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. A display apparatus may implement an image through an array of a plurality of pixels that are two-dimensionally in the display area DA.
The non-display area NDA is an area that does not display an image, and may entirely surround the display area DA. A driver for providing an electrical signal or electric power to display devices in the display area and the like may be in the non-display area NDA. A pad, which is an area to which an electronic device or a printed circuit board may be electrically connected, may be in the non-display area NDA.
The electronic device 1 may have different lengths in an x-axis direction and a y-axis direction. In an embodiment, as shown in
Referring to
The vehicle 1000 may travel on a road and/or track. The vehicle 1000 may move in a set or predetermined direction according to rotation of at least one wheel. In an embodiment, the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction vehicle, a two-wheeled vehicle, a prime mover apparatus, a bicycle, and/or a train traveling on a track.
The vehicle 1000 may include a body having interior trims and exterior trims, and a chassis in which mechanical apparatuses necessary for driving are installed as other parts except for the body. The exterior trims of the body may include a pillar provided at a boundary between a front panel, a bonnet, a roof panel, a rear panel, a trunk, and a door. The chassis of the vehicle 1000 may include a power generating apparatus, a power transmitting apparatus, a driving apparatus, a steering apparatus, a barking apparatus, a suspension apparatus, a transmission apparatus, a fuel apparatus, and front, rear, left and right wheels.
The vehicle 1000 may include a side window glass 1100, a front window glass 1200, a side-view mirror 1300, a cluster 1400, a center fascia 1500, a front passenger seat dashboard 1600, and a display apparatus 2.
The side window glass 1100 and the front window glass 1200 may be partitioned by a pillar between the side window glass 1100 and the front window glass 1200.
The side window glass 1100 may be installed on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be installed on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be adjacent to the cluster 1400. The second side window glass 1120 may be adjacent to the front passenger seat dashboard 1600.
In an embodiment, the side window glasses 1100 may be spaced apart from each other in an x direction or in a −x direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or in the −x direction. In other words, a virtual straight line L connecting the side window glasses 1100 to each other may extend in the x direction or in the −x direction. For example, the virtual straight line L connecting the first side window glass 1110 to the second side window glass 1120 may extend in the x direction or in the −x direction.
The front window glass 1200 may be installed in front of the vehicle 1000. The front window glass 1200 may be between the side window glasses 1100 facing each other.
The side-view mirror 1300 may provide a rear view of the vehicle 1000. The side-view mirror 1300 may be installed on the exterior trim of the body. In an embodiment, a plurality of side-view mirrors 1300 may be provided. One selected from the plurality of side-view mirrors 1300 may be outside the first side window glass 1110. The other among the plurality of side-view mirrors 1300 may be outside the second side window glass 1120.
The cluster 1400 may be in front of a steering wheel. The cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn signal indicator light, a high beam indicator light, a warning light, a seat belt warning light, an odometer, an odometer, an automatic gear selector lever indicator light, a door open warning light, an engine oil warning light, and/or a low fuel warning light.
The center fascia 1500 may include a control panel on which a plurality of buttons for adjusting an audio apparatus, an air conditioning apparatus, and a heater of a seat are arranged. The center fascia 1500 may be on one side of the cluster 1400.
The front passenger seat dashboard 1600 may be spaced apart from the cluster 1400 with the center fascia 1500 interposed therebetween. In an embodiment, the cluster 1400 may correspond to a driver's seat, and the front passenger seat dashboard 1600 may correspond to a front passenger seat. In an embodiment, the cluster 1400 may be adjacent to the first side window glass 1110, and the front passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
In an embodiment, the display apparatus 2 may include a display panel 3, and the display panel 3 may display an image. The display apparatus 2 may be inside the vehicle 1000. In an embodiment, the display apparatus 2 may be between the side window glasses 1100 facing each other. The display apparatus 2 may be on at least one selected from the cluster 1400, the center fascia 1500, and the front passenger seat dashboard 1600.
The display apparatus 2 may include an organic light-emitting display, an inorganic electroluminescent display (inorganic light-emitting display), and a quantum dot display. Hereinafter, an organic light-emitting display including a light-emitting device according to the disclosure is described as an example of the display apparatus 2 according to an embodiment of the disclosure, but in embodiments of the disclosure, various suitable types or kinds of display apparatuses as described above may be used.
Referring to
Referring to
Referring to
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.
When layers constituting the hole transport region, an 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 10−8 torr to about 10−3 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.
The term “C3-C60 carbocyclic group,” as used herein, refers to a cyclic group consisting of carbon only as a ring-forming atom and having three to sixty carbon atoms, and the term “C1-C60 heterocyclic group,” as used herein, refers to a cyclic group that has one to sixty carbon atoms and further has, in addition to carbon, a heteroatom as a ring-forming atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together with each other. In an embodiment, the C1-C60 heterocyclic group has 3 to 61 ring-forming atoms.
The term “cyclic group,” as used herein, may include the C3-C60 carbocyclic group and the C1-C60 heterocyclic group.
The term “π electron-rich C3-C60 cyclic group,” as used herein, refers to a cyclic group that has three to sixty carbon atoms and does not include *—N=*′ as a ring-forming moiety, and the term “π electron-deficient nitrogen-containing C1-C60 cyclic group,” as used herein, refers to a heterocyclic group that has one to sixty carbon atoms and includes *—N=*′ as a ring-forming moiety.
In an embodiment,
The term “cyclic group”, “C3-C60 carbocyclic group”, “C1-C60 heterocyclic group”, “π electron-rich C3-C60 cyclic group”, or “π electron-deficient nitrogen-containing C1-C60 cyclic group,” as used herein, refers to a group condensed to any suitable cyclic group or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.), depending on the structure of a formula in connection with which the terms are used. In an embodiment, “a benzene group” may be a benzo group, a phenyl group, a phenylene group, or the like, which may be easily understood by those of ordinary skill in the art according to the structure of a formula including the “benzene group.”
In an embodiment, examples of a monovalent C3-C60 carbocyclic group and a monovalent C1-C60 heterocyclic group may include a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and examples of a divalent C3-C60 carbocyclic group and a divalent C1-C60 heterocyclic group may include a C3-C1 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C1 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.
The term “C1-C60 alkyl group,” as used herein, refers to a linear or branched aliphatic hydrocarbon monovalent group that has one to sixty carbon atoms, and examples thereof 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 “C1-C60 alkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group,” as used herein, refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C2-C60 alkenyl group.
The term “C2-C60 alkynyl group,” as used herein, refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond at a main chain (e.g., in the middle) or at a terminal end (e.g., the terminus) of the C2-C60 alkyl group, and examples thereof include an ethynyl group and a propynyl group. The term “C2-C60 alkynylene group,” as used herein, refers to a divalent group having substantially the same structure as the C2-C60 alkynyl group.
The term “C1-C60 alkoxy group,” as used herein, refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
The term “C3-C10 cycloalkyl group,” as used herein, refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof 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 a 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 “C3-C10 cycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C3-C1 cycloalkyl group.
The term “C1-C1 heterocycloalkyl group,” as used herein, refers to a monovalent cyclic group that further includes, in addition to a carbon atom, at least one heteroatom as a ring-forming atom and has 1 to 10 carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C1-C10 heterocycloalkylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkyl group.
The term “C3-C10 cycloalkenyl group,” as used herein, refers to a monovalent cyclic group that has three to ten carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity (e.g., is not aromatic), and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group,” as used herein, refers to 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 carbon-carbon double bond in the cyclic structure thereof. Examples of the C1-C10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group,” as used herein, refers to a divalent group having substantially the same structure as the C1-C10 heterocycloalkenyl group.
The term “C6-C60 aryl group,” as used herein, refers to a monovalent group having a carbocyclic aromatic system having six to sixty carbon atoms, and the term “C6-C60 arylene group,” as used herein, refers to a divalent group having a carbocyclic aromatic system having six to sixty carbon atoms. Examples of the C6-C60 aryl group 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 C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be condensed together with each other.
The term “C1-C60 heteroaryl group,” as used herein, refers to a monovalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group,” as used herein, refers to a divalent group having a heterocyclic aromatic system that has, in addition to a carbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60 carbon atoms. Examples of the C1-C60 heteroaryl group 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 C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be condensed together with each other.
The term “monovalent non-aromatic condensed polycyclic group,” as used herein, refers to a monovalent group having two or more rings condensed to each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and non-aromaticity in its molecular structure when considered as a whole (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed polycyclic group 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, refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group,” as used herein refers to a monovalent group having two or more rings condensed to each other, at least one heteroatom other than carbon atoms (for example, having 1 to 60 carbon atoms), as a ring-forming atom, and non-aromaticity in its molecular structure when considered as a whole (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed heteropolycyclic group include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphtho indolyl 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 indenocarbazolyl 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 benzonaphthosilolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term “divalent non-aromatic condensed heteropolycyclic group,” as used herein, refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group,” as used herein, indicates —OA102 (wherein A102 is the C6-C60 aryl group), and the term “C6-C60 arylthio group,” as used herein, indicates —SA103 (wherein A103 is the C6-C60 aryl group).
The term “C7-C60 aryl alkyl group,” as used herein, refers to -A104A105 (where A104 may be a C1-C54 alkylene group, and A105 may be a C6-C59 aryl group), and the term “C2-C60 heteroaryl alkyl group” used herein refers to -A106A107 (where A106 may be a C1-C59 alkylene group, and A107 may be a C1-C59 heteroaryl group).
R10a may be:
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.
The term “hetero atom,” as used herein, refers to any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
“Ph,” as used herein, refers to a phenyl group, “Me,” as used herein, refers to a methyl group, “Et,” as used herein, refers to an ethyl group, “tert-Bu” or “But,” as used herein, refers to a tert-butyl group, and “OMe,” as used herein, refers to a methoxy group.
The term “biphenyl group,” as used herein, refers to “a phenyl group substituted with a phenyl group.” In other words, the “biphenyl group” is a substituted phenyl group having a C6-C60 aryl group as a substituent.
The term “terphenyl group,” as used herein, refers to “a phenyl group substituted with a biphenyl group”. The “terphenyl group” is a substituted phenyl group having, as a substituent, a C6-C60 aryl group substituted with a C6-C60 aryl group.
* and *′, as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula or moiety.
The x-axis, the y-axis, and the z-axis as used herein are not limited to three axes on orthogonal coordinates, and may be construed in a broad sense including the three axes. For example, the x-axis, the y-axis, and the z-axis may be orthogonal to each other, but may refer to different directions that are not orthogonal to each other.
Hereinafter, a compound and light-emitting device according to an embodiment of the disclosure will be described in more detail with reference to the following Synthesis example and Examples. The wording “B was used instead of A,” used in describing Synthesis Examples, indicates that an identical molar equivalent of B was used in place of A.
5.8 g (30.0 mmol) of 2-bromo-1,3-difluorobenzene, 15.0 g (90.0 mmol) of a carbazole, and 19.1 g (90.0 mmol) of potassium phosphate tribasic were placed in a reaction vessel and suspended in 300 ml of dimethylsulfoxide. The resultant reaction mixture was heated and stirred at 160° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 11.6 g (23.7 mmol) of Intermediate [1-A].
11.6 g (23.7 mmol) of Intermediate [1-A], 3.1 g (19.8 mmol) of (6-fluoro-4-methylpyridin-3-yl)boronic acid, 1.2 g (1.0 mmol) of tetrakis(triphenylphosphine)-palladium(0), and 5.5 g (39.6 mmol) of potassium carbonate were placed in a reaction vessel and suspended in 200 ml of a mixture of 1,4-dioxane and water at a volume ratio of 3:1. The resultant reaction mixture was heated and stirred at 110° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 8.3 g (16 mmol) of Intermediate [1-B].
8.3 g (16.0 mmol) of Intermediate [1-B], 3.8 g (19.2 mmol) of 2-methoxy carbazole, and 10.2 g (48.0 mmol) of potassium phosphate tribasic were placed in a reaction vessel and suspended in 160 ml of dimethylsulfoxide. The resultant reaction mixture was heated, and stirred at 160° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 8.4 g (12.1 mmol) of Intermediate [1-C].
8.4 g (12.1 mmol) of Intermediate [1-C] was placed in a reaction vessel and suspended in an excess of bromic acid. The reaction temperature of the resultant reaction mixture was raised to 100° C., and the reaction mixture was stirred for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, a saturated aqueous sodium bicarbonate solution was used for neutralization, and then an organic layer was extracted with ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 6.5 g (9.6 mmol) of Intermediate [1-D].
6.5 g (9.6 mmol) of Intermediate [1-D], 3.4 g (12.5 mmol) of 1-(3-bromophenyl)-1H-benzo[d]imidazole, 4.1 g (19.2 mmol) of potassium phosphate tribasic, 190 mg (1.0 mmol) of copper iodide, and 120 mg (1.0 mmol) of picolinic acid were placed in a reaction vessel and suspended in 100 ml of dimethylsulfoxide. The resultant reaction mixture was heated, and stirred at 160° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and extracted with ethyl acetate. An organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 7.9 g (7.4 mmol) of Intermediate [1-E].
7.9 g (7.4 mmol) of Intermediate [1-E] and 2.1 g (14.8 mmol) of iodomethane were placed in a reaction vessel and suspended in 75 ml of toluene. The resultant reaction mixture was heated and stirred at 110° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 7.2 g (6.0 mmol) of Intermediate [1-F].
7.2 g (6.0 mmol) of Intermediate [1-F] and 2.0 g (12.0 mmol) of ammonium hexafluorophosphate were placed in a reaction vessel and suspended in a mixture of methanol and water at a volume ratio of 2:1. The resultant reaction mixture was stirred at room temperature for 12 hours. A solid thus produced was filtered and separated by column chromatography to obtain 5.9 g (4.8 mmol) of Intermediate [1-G].
5.9 g (4.8 mmol) of Intermediate [1-G], 2.0 g (5.3 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 1.2 g (14.4 mmol) of sodium acetate were suspended in 190 ml of dioxane. The resultant reaction mixture was heated, and stirred at 110° C. for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 1.1 g (1.0 mmol) of Compound 1.
0.9 g (0.8 mmol) of Compound 2 was obtained in substantially the same manner as in Synthesis Example 1, except that a carbazole-Ds, Intermediate [2-A], Intermediate [2-B], Intermediate [2-C], Intermediate [2-D], Intermediate [2-E], Intermediate [2-F], and Intermediate [2-G] were respectively used instead of carbazole, Intermediate [1-A], Intermediate [1-B], Intermediate [1-C], Intermediate [1-D], Intermediate [1-E], Intermediate [1-F], and Intermediate [1-G].
1.0 g (0.9 mmol) of Compound 21 was obtained in substantially the same manner as in Synthesis Example 1, except that iodomethane-D3, Intermediate [21-A], and Intermediate [21-B] were respectively used instead of iodomethane, Intermediate [1-F], and Intermediate [1-G].
6.5 g (9.6 mmol) of Intermediate [1-D], 4.5 g (19.2 mmol) of 1,3-dibromobenzene, 4.1 g (19.2 mmol) of potassium phosphate tribasic, 190 mg (1.0 mmol) of copper iodide, and 120 mg (1.0 mmol) of picolinic acid were placed in a reaction vessel and suspended in 100 ml of dimethylsulfoxide. The resultant reaction mixture was heated, and stirred at 160° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 5.3 g (6.4 mmol) of Intermediate [36-A].
5.3 g (6.4 mmol) of Intermediate [36-A], 2.6 g (7.7 mmol) of N1-([1,1′:3′,1″-terphenyl]-2′-yl)benzene-1,2-diamine, 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium, 0.2 g (0.5 mmol) of SPhos, and 1.2 g (12.8 mmol) of sodium tert-butoxide were placed in a reaction vessel and suspended in 60 ml of toluene. The reaction temperature of the resultant reaction mixture was raised to 110° C., and the reaction mixture was stirred for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 4.9 g (4.5 mmol) of Intermediate [36-B].
4.9 g (4.5 mmol) of Intermediate [36-B], 30 ml (225.0 mmol) of triethyl orthoformate, and 2.1 ml (24.8 mmol) of HCl 35 wt % solution were placed in a reaction vessel, heated, and stirred at 80° C. for 12 hours. After completion of the reaction, the resultant reaction mixture was cooled to room temperature, and the residue, from which the solvent was removed, was separated by column chromatography to obtain 4.1 g (3.6 mmol) of Intermediate [36-C].
4.1 g (3.6 mmol) of Intermediate [36-C] and 1.2 g (7.2 mmol) of ammonium hexafluorophosphate were placed in a reaction vessel and suspended in a mixture of methanol and water at a volume ratio of 2:1. The resultant reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, a solid thus produced was filtered and separated by column chromatography to obtain 4.0 g (3.2 mmol) of Intermediate [36-D].
4.0 g (3.2 mmol) of Intermediate [36-D], 1.3 g (3.5 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 0.8 g (9.6 mmol) of sodium acetate were suspended in 130 ml of dioxane. The resultant reaction mixture was heated, and stirred at 110° C. for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 1.2 g (0.9 mmol) of Compound 36.
0.8 g (0.7 mmol) of Compound 84 was obtained in substantially the same manner as in Synthesis Example 1, except that 2-methoxy-6-phenyl-9H-carbazole, Intermediate [84-A], Intermediate [84-B], Intermediate [84-C], Intermediate [84-D], and Intermediate [84-E] were respectively used instead of 2-methoxy carbazole, Intermediate [1-C], Intermediate [1-D], Intermediate [1-E], Intermediate [1-F], and Intermediate [1-G].
11.6 g (23.7 mmol) of Intermediate [1-A], 3.4 g (15.8 mmol) of (6-bromo-4-methyl-d3-pyridin-3-yl)boronic acid, 1.4 g (1.2 mmol) of tetrakis(triphenylphosphine)-palladium(0), and 4.4 g (31.6 mmol) of potassium carbonate were placed in a reaction vessel and suspended in 160 ml of a mixture of 1,4-dioxane and water at a volume ratio of 3:1. The resultant reaction mixture was heated and stirred at 110° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 7.3 g (12.7 mmol) of Intermediate [16-A].
7.3 g (12.7 mmol) of Intermediate [16-A], 2.9 g (19.1 mmol) of 3-methoxy phenylboronic acid, 0.7 g (0.6 mmol) of tetrakis(triphenylphosphine)-palladium(0), and 3.5 g (25.4 mmol) of potassium carbonate were placed in a reaction vessel and suspended in 130 ml of a mixture of 1,4-dioxane and water at a volume ratio of 3:1. The resultant reaction mixture was heated and stirred at 110° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 5.8 g (9.5 mmol) of Intermediate [16-B].
5.8 g (9.5 mmol) of Intermediate [16-B] was placed in a reaction vessel and suspended in an excess of bromic acid. The reaction temperature of the resultant reaction mixture was raised to 100° C., and the reaction mixture was stirred for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, a saturated aqueous sodium bicarbonate solution was used for neutralization, and then an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 4.5 g (7.6 mmol) of Intermediate [16-C].
4.5 g (7.6 mmol) of Intermediate [16-C], 2.5 g (9.112.5 mmol) of 1-(3-bromophenyl)-1H-benzo[d]imidazole, 3.2 g (15.2 mmol) of potassium phosphate tribasic, 150 mg (0.8 mmol) of copper iodide, and 120 mg (1.0 mmol) of picolinic acid were placed in a reaction vessel and suspended in 80 ml of dimethylsulfoxide. The resultant reaction mixture was heated, and stirred at 160° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 4.6 g (5.9 mmol) of Intermediate [16-D].
4.6 g (5.9 mmol) of Intermediate [16-D], 3.8 g (8.9 mmol) of diphenyliodonium hexafluorophosphate, and 60 mg (0.3 mmol) of copper acetate were suspended in 60 ml of dimethylsulfoxide. The resultant reaction mixture was heated, and stirred at 110° C. for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, 120 ml of distilled water was added thereto, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 4.9 g (4.1 mmol) of Intermediate [16-E].
4.9 g (4.1 mmol) of Intermediate [16-E], 1.7 g (4.5 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 1.0 g (12.3 mmol) of sodium acetate were suspended in 160 ml of dioxane. The resultant reaction mixture was heated, and stirred at 110° C. for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, 130 ml of distilled water was added thereto, and an organic layer was extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution, and dried by using sodium sulfate. The residue, from which the solvent was removed, was separated by column chromatography to obtain 400 mg (0.5 mmol) of Compound 16.
1H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples 1 to 6 are shown in Table 1. Synthesis methods of other compounds in addition to compounds shown in Table 1 may be easily recognized by those of ordinary skill in the art by referring to the synthesis paths and source materials.
1H NMR (CDCl3, 400 MHz)
As an anode, a 15 Ω/cm2 (1,200 Å) ITO glass substrate (available from Corning Co., Ltd) was cut to a size of 50 mm×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes in each solvent, cleaned by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes, and was mounted on a vacuum deposition apparatus.
On the anode, 2-TNATA was vacuum-deposited to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred as “NPB”) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.
Compound 1, Compound H1-1, and Compound E2 were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 300 Å. In this regard, an amount of Compound 1 was 10 wt % based on a total weight (100 wt %) of the emission layer, and a weight ratio of Compound H1-1 to Compound E2 was adjusted to 5:5.
Compound E1 was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, and Alq3 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å. LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited thereon to form a cathode having a thickness of 3,000 Å, thereby completing manufacture of an organic light-emitting device.
An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that compounds shown in Table 2 were used to form the emission layer. Evaluation Example 1
The driving voltage (V) at 1,000 cd/m2, luminescence efficiency (cd/A), color coordinates (CIE_y), maximum emission wavelength (nm), and lifespan (T95) of the organic light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 to 4 were each measured by using a Keithley SMU 236 and a luminance meter PR650. The results are shown in Table 3. In Table 3, the lifespan (T95) indicates a time (hr) for the luminance to reach 95% of its initial luminance, and the luminescence efficiency and lifespan (T95) are expressed as relative values with respect to Comparative Example 1.
From Table 3, it can be seen that the organic light-emitting devices of Examples 1 to 6 have lower driving voltage, better luminescence efficiency, and/or better lifespan characteristics than those of the organic light-emitting devices of Comparative Examples 1 to 4.
A light-emitting device including the organometallic compound may have low driving voltage, high efficiency, and long lifespan, and thus, may be used to manufacture a high-quality electronic apparatus having excellent light efficiency and long lifespan.
It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims, and equivalents thereof.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2022-0043645 | Apr 2022 | KR | national |
