Patent Application
20220024958
This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0086448, filed on Jul. 13, 2020, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.
One or more aspects of embodiments of the present disclosure relate to a light-emitting device and an electronic apparatus including the light-emitting device.
Light-emitting devices are self-emission devices that have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and/or response speed.
Light-emitting devices may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked 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, recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state to thereby generate light.
One or more aspects of embodiments of the present disclosure are directed toward a light-emitting device having high luminescence efficiency and long lifespan and an electronic apparatus including the light-emitting device.
Additional aspects 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, a light-emitting device may include:
a first electrode;
a second electrode facing the first electrode; and
an interlayer located between the first electrode and the second electrode, the interlayer including an emission layer,
wherein the interlayer may include:
i) a first compound represented by Formula 1; and
ii) a second compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescent light, or any combination thereof, and
the first compound, the second compound, the third compound, and the fourth compound may be different from one another:
wherein, in Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
in Formula 1, X1 to X4 may each independently be C or N,
in Formula 1, i) a bond between X1 and M may be a coordinate bond, and ii) one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M may be a coordinate bond, and the other two bonds may each be a covalent bond,
in Formula 1, ring CY1 may be i) a X1-containing 5-membered ring, ii) a X1, containing 5-membered ring condensed with at least one 6-membered ring, or iii) a X1-containing 6-membered ring,
in Formula 1, ring CY2 may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
in Formula 1, X31 to X36 and X41 to X44 may each independently be C or N,
in Formula 1, X51 may be *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*, *—Ge(R5a)(R5b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, or *—C═C—*′, and * and *′ may each indicate a binding site to an adjacent atom,
in Formula 1, L1 may be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
in Formula 1, b1 may be an integer from 1 to 5,
in Formula 1, R1 to R5, R5a, and R5b may each independently be a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1(Q2), —C(═O)(Q1), —S(═O)2(O1), or —P(═O)(Q1)(Q2),
wherein, in Formula 1, c1 may be an integer from 0 to 5, a1 and a4 may each independently be an integer from 0 to 4, a2 may be an integer from 0 to 10, and a3 may be an integer from 0 to 6, provided that the sum of a1 to a4 may be 1 or greater, and at least one of *-(L1)b1-(R1)c1(s) in the number of a1, at least one of R2(s) in the number of a2, at least one of R3(s) in the number of a3, at least one of R4(s) in the number of a4, or any combination thereof may each independently be the group represented by Formula 1-1 or the group represented by Formula 1-2,
in Formulae 1-1 and 1-2, L7 may be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
in Formulae 1-1 and 1-2, b7 may be an integer from 1 to 5,
in Formulae 1-1 and 1-2, ring CY7 may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
in Formulae 1-1 and 1-2, n7 may be an integer from 1 to 5,
in Formula 1-1, ring CY8 may be a non-aromatic C3-C60 carbocyclic group or a non-aromatic C1-C60 heterocyclic group,
in Formulae 1-1 and 1-2, R7 to R9 may each be understood by referring to the description of R1 provided herein,
in Formulae 1-1 and 1-2, a7 and a8 may each independently be an integer from 0 to 20,
in Formula 3, ring CY71 and ring CY72 may each independently be a TT electron-rich C3-C60 cyclic group or a pyridine group,
in Formula 3, X71 may be a single bond or a linking group including O, S, N, B, C, Si, or any combination thereof,
in Formula 3, * indicates a binding site to an adjacent atom,
at least two groups represented by *-(L1)b1-(R1)c1 in the number of a1 may optionally be bound to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of R2(s) in the number of a2 may optionally be bound to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of R3(s) in the number of a3 may optionally be bound to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of R4(s) in the number of a4 may optionally be bound to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
at least two of R1 to R5, R5a, and R5b(s) may optionally be bound to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and
R10a may be:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each independently unsubstituted or substituted with deuterium, —F, —C1, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
wherein 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 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each independently 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof, and
the following compounds may be excluded from the third compound:
According to one or more embodiments, an electronic apparatus may include the light-emitting device.
According to one or more embodiments, an organometallic compound may be represented by Formula 1:
The above and other aspects, features, and advantages 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. 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 the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
Expressions such as “at least selected from,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure.”
A light-emitting device may include: 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, wherein the interlayer may include:
i) a first compound represented by Formula 1; and
ii) a second compound including at least one π electron-deficient nitrogen-containing C1-C60 cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescent light, or any combination thereof, and
the first compound, the second compound, the third compound, and the fourth compound may be different from one another:
wherein Formula 1 may be understood by referring to the description of Formula 1 provided herein.
wherein, in Formula 3, ring CY71 and ring CY72 may each independently be a π electron-rich C3-C60 cyclic group or a pyridine group,
in Formula 3, X71 may be a single bond or a linking group including O, S, N, B, C, Si, or any combination thereof, and
in Formula 3, * indicates a binding site to an adjacent atom.
the following compounds may be excluded from the third compound:
The second compound may include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
In some embodiments, the light-emitting device may further include at least one of the second compound and the third compound, in addition to the first compound.
In some embodiments, the light-emitting device may further include the fourth compound, in addition to the first compound.
In some embodiments, the light-emitting device may include the first compound, the second compound, the third compound, and the fourth compound.
In some embodiments, the interlayer may include the second compound. The interlayer may further include, in addition to the first compound and the second compound, the third compound, the fourth compound, or any combination thereof.
In some embodiments, a difference (an absolute value) between the triplet energy level (in electron Volts, eV) of the fourth compound and the singlet energy level (in electron Volts, eV) of the fourth compound may be about 0 eV or higher and about 0.5 eV or lower (or, about 0 eV or higher and about 0.3 eV or lower).
In some embodiments, the fourth compound may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
In some embodiments, the fourth compound may be a C8-C60 polycyclic group-containing compound including at least two cyclic groups that are condensed with each other sharing a boron atom (B).
In some embodiments, the fourth compound may include a condensed ring in which at least one third ring may be condensed with at least one fourth ring,
the third ring may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, and
the fourth ring may be a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
In one or more embodiments, the interlayer may include the fourth compound. The interlayer may include, in addition to the first compound and the fourth compound, the second compound, the third compound, or any combination thereof.
In one or more embodiments, the interlayer may include the third compound. In some embodiments, the third compound may not include a compound represented by Formula 3-1.
The emission layer in the interlayer may include: i) the first compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof.
The emission layer may emit phosphorescent light or fluorescent light emitted from the first compound. In some embodiments, phosphorescent light or fluorescent light emitted from the first compound may be blue light.
In some embodiments, the emission layer in the light-emitting device may include the first compound and the second compound, and the first compound and the second compound may form an exciplex.
In some embodiments, the emission layer in the light-emitting device may include the first compound, the second compound, and the third compound, and the first compound and the second compound may form an exciplex.
In some embodiments, the emission layer in the light-emitting device may include the first compound and the fourth compound, and the fourth compound may serve to improve color purity, luminescence efficiency, and/or lifespan characteristics of the light-emitting device.
In some embodiments, the second compound may include a compound represented by Formula 2:
wherein, in Formula 2,
L51 to L53 may each independently be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
b51 to b53 may each independently be an integer from 1 to 5,
X54 may be N or C(R54), X55 may be N or C(R55), X56 may be N or C(R56), and at least one selected from X54 to X56 may be N,
R51 to R56 may respectively be understood by referring to the descriptions of R51 to R56 provided herein, and
R10a may be understood by referring to the description of R10a provided herein.
In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
wherein, in Formulae 3-1 to 3-5,
ring CY71 to ring CY74 may each independently be a π electron-rich C3-C60 cyclic group or a pyridine group,
X82 may be a single bond, O, S, N-[(L82)b82-R82], C(R82a)(R82b), or Si(R82a)(R82b),
X83 may be a single bond, O, S, N-[(L83)b83-R83], C(R83a)(R83b), or Si(R83a)(R83b),
X84 may be O, S, N-[(L84)b84-R84], C(R84a)(R84b), or Si(R84a)(R84b),
X85 may be C or Si,
L81 to L85 may each independently be a single bond, *—C(Q4)(Q5)-*′, *—Si(Q4)(Q5)-*′, a π electron-rich C3-C60 cyclic group unsubstituted or substituted with at least one R10a, or a pyridine group unsubstituted or substituted with at least one R10a, wherein Q4 and Q5 may each be understood by referring to the description of Q1 provided herein,
b81 to b85 may each independently be an integer from 1 to 5,
R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b may respectively be understood by referring to the descriptions of R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, and R84b provided herein,
a71 to a74 may each independently be an integer from 0 to 20, and
R10a may be understood by referring to the description of R10a provided herein.
In some embodiments, the fourth compound may be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
wherein, in Formulae 502 and 503,
ring A501 to ring A504 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
Y505 may be O, S, N(R505), B(R505), C(R505a)(R505b), or Si(R505a)(R505b),
Y506 may be O, S, N(R506), B(R506), C(R506a)(R506b), or Si(R506a)(R506b),
Y507 may be O, S, N(R507), B(R507), C(R507a)(R507b), or Si(R507a)(R507b),
Y508 may be O, S, N(R508), B(R508), C(R508a)(R508b), or Si(R508a)(R508b),
Y51 and Y52 may each independently be B, P(═O), or S(═O),
R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b may respectively be understood by referring to the descriptions of R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b provided herein,
a501 to a504 may each independently be an integer from 0 to 20, and
R10a may be understood by referring to the description of R10a provided herein.
In Formula 1, M may be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
In Formula 1, X1 to X4 may each independently be C or N.
In some embodiments, in Formula 1, X1 may be C, and C may be a carbon atom in a carbene moiety.
In one or more embodiments, in Formula 1, X1 may be N.
In one or more embodiments, in Formula 1, X2 and X3 may each be C, and X4 may be N.
In Formula 1, i) a bond between X1 and M may be a coordinate bond, and ii) one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M may be a coordinate bond, and the other two bonds may each be a covalent bond.
In some embodiments, in Formula 1, a bond between X2 and M and a bond between X3 and M may each be a covalent bond, and a bond between X4 and M may be a coordinate bond.
In Formula 1, ring CY1 may be i) a X1-containing 5-membered ring, ii) a X1, containing 5-membered ring condensed with at least one 6-membered ring, or iii) a X1-containing 6-membered ring. In some embodiments, in Formula 1, ring CY1 may be i) a X1-containing 5-membered ring or ii) a X1-containing 5-membered ring condensed with at least one 6-membered ring. For example, ring CY1 may include a 5-membered ring bound to M in Formula 1 via X1.
In some embodiments, the X1-containing 5-membered ring in ring CY1 in Formula 1 may be a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group.
In some embodiments, the 6-membered ring that may be condensed to the X1-containing 5-membered ring in ring CY1 in Formula 1 or the X1-containing 6-membered ring may be a benzene group, a pyridine group, or a pyrimidine group.
In some embodiments, in Formula 1, a group represented by may be represented by one of Formulae CY1-1 to CY1-42:
wherein, in Formulae CY1-1 to CY1-42,
Y1 may be O, S, N, C, or Si,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to an adjacent atom in Formula 1.
In some embodiments, in Formulae CY1-1 to CY1-8, X1 may be C, and X1 in Formulae CY1-9 to CY1-42 may be N.
In Formula 1, ring CY2 may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
In some embodiments, ring CY2 may be a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.
In some embodiments, in Formula 1, a group represented by
may be a group represented by one of Formulae CY2-1 to CY2-11:
wherein, in Formulae CY2-1 to CY2-11,
Y2 may be O, S, N, C, or Si,
* indicates a binding site to M in Formula 1,
*′ indicates a binding site to ring CY1 in Formula 1, and
*″ indicates a binding site to X51 in Formula 1.
In Formula 1, X31 to X36 and X41 to X44 may each independently be C or N.
In some embodiments, in Formula 1, X31 to X36 and X41 to X44 may each be C.
In Formula 1, X51 may be *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—Ge(R5a)(R5b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5a)═C(R5b)—*′, *—C(═S)—*′, or *—C═C—*′. * and *′ each indicate a binding site to an adjacent atom. R5, R5a, and R5b may respectively be understood by referring to the descriptions of R5, R5a, and R5b provided herein. R5a and R5b may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a (e.g., Compound 109, and/or the like).
In some embodiments, in Formula 1, X51 may be *—N(R5)—*′, *—B(R5)—*′, *—C(R5a)(R5b)—*′, *—Si(R5a)(R5b)—*′, *—S—*′, or *—O—*′.
L1 in Formula 1 may be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In Formula 1, b1 indicates the number of L1(s), and b1 may be an integer from 1 to 5. When b1 is 2 or greater, at least two L1(s) may be identical to different from each other. In some embodiments, b1 may be 1 or 2.
In Formula 1, R1 to R5, R5a, and R5b may each independently be a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —C(═O)(Q1), —S(═O)2(O1), or —P(═O)(Q1)(Q2):
Formulae 1-1 and 1-2 may each be understood by referring to the descriptions of Formulae 1-1 and 1-2 provided herein.
In Formula 1, c1 may be an integer from 0 to 5, a1 and a4 may each independently be an integer from 0 to 4, a2 may be an integer from 0 to 10, and a3 may be an integer from 0 to 6, provided that the sum of a1 to a4 may be 1 or greater, and at least one of *-(L1)b1-(R1)c1(s) in the number of a1, at least one of R2(s) in the number of a2, at least one of R3(s) in the number of a3, at least one of R4(s) in the number of a4, or any combination thereof may each independently be the group represented by Formula 1-1 or the group represented by Formula 1-2. For example, the organometallic compound represented by Formula 1 may include the group represented by Formula 1-1, the group represented by Formula 1-2, or any combination thereof.
In some embodiments, in Formula 1, a4 may be an integer from 1 to 4, at least one of R4(s) in the number of a4 may each independently be the group represented by Formula 1-1 or the group represented by Formula 1-2.
L7 in Formulae 1-1 and 1-2 may be a single bond, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In Formulae 1-1 and 1-2, b7 indicates the number of L7(s), and b7 may be an integer from 1 to 5. When b7 is 2 or greater, at least two L7(s) may be identical to different from each other. In some embodiments, b7 may be 1 or 2.
In Formulae 1-1 and 1-2, ring CY7 may be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group.
In some embodiments, in Formulae 1-1 and 1-2, ring CY7 may be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which at least one first ring and at least one second ring are condensed,
the first ring may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group, and
the second ring may be a pyrrole group, a furan group, a thiophene group, a silole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a 1,2-azaborinine group, a 1,3-azaborinine group, a 1,4-azaborinine group, a 1,2-dihydro-1,2-azaborinine group, a 1,4-oxaborinine group, a 1,4-thiaborinine group, or a 1,4-dihydroborinine group.
In one or more embodiments, in Formulae 1-1 and 1-2, ring CY7 may be a benzene group, a naphthalene group, a phenanthrene group, a carbazole group, a [1,2]azaborinino[1,2-a][1,2]azaborinine group, or a benzo[1,2]azaborinino[1,2-a][1,2]azaborinine group.
In one or more embodiments, in Formulae 1-1 and 1-2, ring CY7 may be a group represented by one of Formulae CY7-1 to CY7-33:
In Formulae CY7-1 to CY7-33, * indicates a binding site to L7 in Formulae 1-1 and 1-2.
In Formulae 1-1 and 1-2, n7 indicates the number of groups represented by
and n7 may be an integer from 1 to 5. When n7 is 2 or greater, at least two groups represented by
may be identical to or different from each other. In some embodiments, n7 may be 1.
In Formula 1-1, ring CY8 may be a non-aromatic C3-C60 carbocyclic group or a non-aromatic C1-C60 heterocyclic group.
In some embodiments, in Formula 1-1, ring CY8 may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norobornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, or a bicyclo[2.2.2]octane group.
In one or more embodiments, in Formula 1-1, ring CY8 may be a group represented by one of Formulae CY8-1 to CY8-8:
wherein, in Formulae CY8-1 to CY8-8, * indicates a binding site to an adjacent atom in Formula 1, and *′ indicates a binding site to L7 in Formula 1-1.
In Formulae 1-1 and 1-2, R7 to R9 may each be understood by referring to the descriptions of R1 provided herein.
In Formulae 1-1 and 1-2, a7 and a8 may respectively indicate the number of R7(S) and R8(s), and a7 and a8 may each independently be an integer from 0 to 20. When a7 is 2 or greater, at least two R7(s) may be identical to or different from each other. When a8 is 2 or greater, at least two R8(s) may be identical to or different from each other.
In Formula 1, i) at least two of groups represented by *-(L1)b1-(R1)c1 in the number of a1 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, ii) at least two of R2(s) in the number of a2 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, iii) at least two of R3 in the number of a3 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, iv) at least two of R4 in the number of a4 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and/or v) at least two of R1 to R5, R5a, and R5b may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a. The first linking group may be selected from *—N(R95)—*′, *—B(R95)—*′, *—P(R95)—*, *—C(R95a)(R95b)—*′, *—Si(R95a)(R95b)—*′, *—Ge(R95a)(R95b)—*′, *—Se—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R95)=*′, *═C(R95)—*′, *—C(R95a)═C(R95b)—*′, *—C(═S)—*′, and *—C═C—*′, and R95, R95a, and R95b may each be understood by referring to the description of R10a provided herein.
In some embodiments, the first compound represented by Formula 1 may include at least one deuterium.
In one or more embodiments, the group represented by Formula 1-1 and the group represented by Formula 1-2 may each include at least one deuterium.
In one or more embodiments, in Formula 1, 1) a1 may not be 0, and 2) in at least one of *-(L1)b1-(R1)c1 in a1 number of *-(L1)b1-(R1)c1(s), i) L1 may not be a single bond, and ii) at least one of R1(s) in the number of c1 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, in Formula 1, the group represented by *-(L1)b1-(R1)c1 may include at least one deuterium.
In one or more embodiments, in Formula 1, the group represented by
may be represented by one of Formulae CY1 (1) to CY1(6):
wherein, in Formulae CY1 (1) to CY1 (6),
X1 may be selected from O, S, N(R21), C(R21)(R22), and Si(R21)(R22),
L11 and c11 may respectively be understood by referring to the descriptions of L1 and c1 provided herein,
R11 to R13 may each be understood by referring to the description of R1 provided herein, wherein R11 to R13 may not each be hydrogen,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to an adjacent atom in Formula 1.
In some embodiments, in Formulae CY1(1) to CY1(5), 1) L-n may not be a single bond, and 2) at least one of R-M(S) in the number of c11 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
In some embodiments, in Formulae CY1(1) to CY1(4), X1 may be C, and in Formulae CY1(5) and CY1(6), X1 may be N.
In some embodiments, L-n in Formulae CY1(1) to CY1(5) may be a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a.
In one or more embodiments, the group represented by
in Formula 1 may be one of groups represented by Formulae CY2(1) to CY2(26):
wherein, in Formulae CY2(1) to CY2(26),
X2 may be understood by referring to the description of X21 provided herein,
X21 may be selected from O, S, N(R21), C(R21)(R22), and Si(R21)(R22),
R21 to R23 may each be understood by referring to the description of R2 provided herein, wherein R21 to R23 may not each be hydrogen,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to ring CY1 in Formula 1, and
*″ indicates a binding site to X51 in Formula 1.
In one or more embodiments, in Formula 1, the group represented by
may be a group represented by one of Formulae CY3(1) to CY3(7):
wherein, in Formulae CY3(1) to CY3(7),
X3 may be understood by referring to the description of X3 provided herein,
R31 to R36 may each be understood by referring to the description of R3 provided herein, wherein R31 to R36 may not each be hydrogen,
* indicates a binding site to M in Formula 1,
*′ indicates a binding site to an adjacent atom in Formula 1, and
*″ indicates a binding site to X51 in Formula 1.
In one or more embodiments, in Formula 1, the group represented by
may be a group represented by one of Formulae CY4(1) to CY4(8):
wherein, in Formulae CY4(1) to CY4(8),
X4 may be understood by referring to the description of X4 provided herein,
T4 may be the group represented by Formula 1-1 or the group represented by Formula 1-2,
R41, R43, and R44 may each be understood by referring to the description of R4 provided herein, wherein R41, R43, and R44 may not each be hydrogen,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to an adjacent atom in Formula 1.
In Formula 2, b51 to b53 may respectively indicate the number of L51(s) to L53(s), and b51 to b53 may each be an integer from 1 to 5. When b51 is 2 or greater, at least two L51(s) may be identical to or different from each other, when b52 is 2 or greater, at least two L52(s) may be identical to or different from each other, and when b53 is 2 or greater, at least two L53(s) may be identical to or different from each other. In some embodiments, b51 to b53 may each independently be 1 or 2.
In Formulae 1, 1-1, 1-2 and 2, L1, L7, and L51 to L53 may each independently be:
a single bond; or
a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzooxasiline group, a dibenzothiasiline group, a dibenzodihydroazasiline group, a dibenzodihydrodisiline group, a dibenzodihydrosiline group, a dibenzodioxane group, a dibenzooxathiene group, a dibenzooxazine group, a dibenzopyran group, a dibenzodithiine group, a dibenzothiazine group, a dibenzothiopyran group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group, or a dibenzodihydropyrazine group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl (dibenzothienyl) group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O(Q31), —S(Q31), —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof,
wherein Q31 to Q33 may each independently be hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
In some embodiments, in Formula 2, a bond between L51 and R51, a bond between L52 and R52, a bond between L53 and R53, a bond between at least two L51(s), a bond between at least two L52(s), a bond between at least two L53(s), a bond between L51 and a carbon atom between X54 and X55 in Formula 2, a bond between L52 and a carbon atom between X54 and X56 in Formula 2, and a bond between L53 and a carbon atom between X55 and X56 in Formula 2 may each be a “carbon-carbon single bond”.
In Formula 2, X54 may be N or C(R54), X55 may be N or C(R55), X56 may be N or C(R56), and at least one selected from X54 to X56 may be N, wherein R54 to R56 may respectively be understood by referring to the descriptions of R54 to R56 provided herein. In some embodiments, two or three of X54 to X56 may each be N.
In the present specification, R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a and R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —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 respectively be understood by referring to the descriptions of Q1 to Q3 provided herein.
In some embodiments, i) in Formula 1, R1 to R5, R5a, and R5b, other than the group represented by Formula 1-1 and the group represented by Formula 1-2, ii) in Formulae 1-1 and 1-2, R7 to R9, iii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iv) R10a may each independently be:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl (thienyl) group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl (benzothienyl) group, an benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by Formula 91, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2FI, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —O(Q31), —S(Q31), —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof; or
—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),
wherein Q1 to Q3 and Q31 to Q33 may each independently be:
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2;
an n-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 phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each independently unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof:
wherein, in Formula 91,
ring CY91 to ring CY92 may each independently be a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
X91 may be a single bond, O, S, N(R91), B(R91), C(R91a)(R91b), or Si(R91a)(R91b),
R91, R91a, and R91b may respectively be understood by referring to the descriptions of R82, R82a, and R82b provided herein,
R10a may be understood by referring to the description of R10a provided herein, and
* indicates a binding site to an adjacent atom.
In some embodiments, in Formula 91,
ring CY91 and ring CY92 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, each independently unsubstituted or substituted with at least one R10a,
R91, R91a and R91b may each independently be:
hydrogen or a C1-C10 alkyl group; or
a phenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each independently unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
In one or more embodiments, i) in Formula 1, R1 to R5, R5a, R5b, and R7 to R9, other than the group represented by Formula 1-1 and the group represented by Formula 1-2, ii) R51 to R56, R71 to R74, R81 to R85, R82a, R82b, R83a, R83b, R84a, R84b, R500a, R500b, R501 to R508, R505a, R505b, R506a, R506b, R507a, R507b, R508a, and R508b in Formulae 2, 3-1 to 3-5, 502, and 503, and iii) R10a may each independently be hydrogen, deuterium, —F, a cyano group, a nitro group, —CH3, —CD3, —CD2FI, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one of Formulae 9-1 to 9-19, a group represented by one of Formulae 10-1 to 10-246, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), or —P(═O)(Q1)(Q2), wherein Q1 to Q3 may respectively be understood by referring to the descriptions of Q1 to Q3
provided herein:
wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-246, * indicates a binding site to an adjacent atom, “Ph” represents a phenyl group, and “TMS” represents a trimethylsilyl group.
In Formulae 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 may respectively indicate the number of R71(s) to R74(s) and R501(s) to R504(s), and a71 to a74 and a501 to a504 may each independently be an integer from 0 to 20. When a71 is 2 or greater, at least two R71(s) may be identical to or different from each other, when a72 is 2 or greater, at least two R72(s) may be identical to or different from each other, when a73 is 2 or greater, at least two R73(s) may be identical to or different from each other, when a74 is 2 or greater, at least two R74(s) may be identical to or different from each other, when a501 is 2 or greater, at least two R501(s) may be identical to or different from each other, when a502 is 2 or greater, at least two R502(s) may be identical to or different from each other, when a503 is 2 or greater, at least two R503(s) may be identical to or different from each other, and when a504 is 2 or greater, at least two R504(s) may be identical to or different from each other. a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
In Formula 1, i) at least two of groups represented by *-(L1)b1-(R1)c1 in the number of a1 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, ii) at least two of R2(s) in the number of a2 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, iii) at least two of R3 in the number of a3 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, iv) at least two of R4 in the number of a4 may optionally be bound to each other (via a single bond, a double bond, or a first linking group) to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and v) at least two of R1 to R5, R5a, and R5b may optionally be bound to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a. The first linking group may be selected from *—N(R95)—*′, *—B(R95)—*′, *—P(R95)—*′, *—C(R95a)(R95b)—*′, *—Si(R95a)(R95b)—*′, *—Ge(R95a)(R95b)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R95)=*′, *═C(R95)—*′, *—C(R95a)═C(R95b)—*′, *—C(═S)—*′, and *—C≡C—*′, and R95, R95a, and R95b may each be understood by referring to the description of R1 provided herein.
In some embodiments, in Formula 2, the group represented by *—(N51)b51—R51 and the group represented by *-(L52)b52-R52 may not be a phenyl group.
In some embodiments, in Formula 2, the group represented by *-(L51)b51-R51 may be identical to the group represented by *-(L52)b52-R52.
In one or more embodiments, in Formula 2, the group represented by *-(L51)b51-R51 and the group represented by *-(L52)b52-R52 may be different from each other.
In one or more embodiments, in Formula 2, b51 and b52 may each independently be 1,2, or 3, L51 and L52 may each independently be a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, or a triazine group, each independently unsubstituted or substituted with at least one R10a.
In some embodiments, in Formula 2, R51 and R52 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3),
wherein Q1 to Q3 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each independently 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.
In some embodiments,
in Formula 2, the group represented by *-(L51)b51-R51 may be a group represented by one of Formulae CY51-1 to CY51-26,
in Formula 2, the group represented by *-(L52)b52-R52 may be a group represented by one of Formulae CY52-1 to CY52-26, and/or
in Formula 2, the group represented by *-(L53)b53-R53 may be a group represented by one of Formulae CY53-1 to CY53-27, —C(Q1)(Q2)(Q3), or —Si(Q1)(Q2)(Q3):
wherein, in Formulae CY51-1 to CY51-26, CY52-1 to CY52-26, and CY53-1 to CY53-27,
Y63 may be a single bond, O, S, N(R63), B(R63), C(R63a)(63b), or Si(R63a)(R63b),
Y64 may be a single bond, O, S, N(R64), B(R64), C(R64a)(R64b), or Si(R64a)(R64b),
Y67 may be a single bond, O, S, N(R67), B(R67), C(R67a)(R67b), or Si(R67a)(R67b),
Y68 may be a single bond, O, S, N(R68), B(R68), C(R68a)(R68b), or Si(R68a)(R68b),
Y63 and Y64 in Formulae CY51-16 and CY51-17 may not be a single bond at the same time,
Y67 and Y68 in Formulae CY52-16 and CY52-17 may not be a single bond at the same time,
R51a to R51e, R61 to R64, R63a, R63b, R64a, and R64b may each be understood by referring to the description of R51, and R51a to R51e may not each be hydrogen,
R52a to R52e, Res to R68, R67a, R67b, R68a, and R68b may each be understood by referring to the description of R52, and R52a to R52e may not each be hydrogen,
R53a to R53e, R69a, and R69b may each be understood by referring to the description of R53, and R53a to R53e may not each be hydrogen, and
* indicates a binding site to an adjacent atom.
In some embodiments, R51a to R51e and R52a to R52e in Formulae CY51-1 to CY51-26 and Formula CY52-1 to 52-26 may each independently be:
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, or a group represented by Formula 91, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, or any combination thereof; or
—C(Q1)(Q2)(Q3) or —Si(Q1)(Q2)(Q3),
wherein Q1 to Q3 may each independently be a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each independently unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof,
in Formulae CY51-16 and CY51-17, i) Y63 may be O or S, and Y64 may be Si(R64a)(R64b), or ii) Y63 may be Si(R63a)(R63b), and Y64 may be O or S,
in Formulae CY52-16 and CY52-17, i) Y67 may be O or S, and Y68 may be Si(R68a)(R68b), or ii) Y67 may be Si(R67a)(R67b), and Y68 may be O or S.
In Formulae 3-1 to 3-5, L81 to L85 may each independently be:
a single bond; or
*—C(Q4)(Q5)-*′ or *—Si(Q4)(Q5)—*′; or
a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —O(Q31), —S(Q31), —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —P(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof,
wherein Q4, Q5, and Q31 to Q33 may each independently be hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
In some embodiments, in Formulae 3-1 and 3-2, the group represented by
may be a group represented by one of Formulae CY71-1 (1) to CY71-1(8), and/or
in Formulae 3-1 and 3-3, the group represented by
may be a group represented by one of Formulae CY71-2(1) to CY71-2(8), and/or
in Formulae 3-2 and 3-4, the group represented by
may be a group represented by one of Formulae CY71-3(1) to CY71-3(32), and/or
in Formulae 3-3 to 3-5, the group represented by
may be a group represented by one of Formulae CY71-4(1) to CY71-4(32), and/or
in Formula 3-5, the group represented by
may be a group represented by one of Formulae CY71-5(1) to CY71-5(8):
wherein, in Formulae CY71-1 (1) to CY71-1 (8), CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), CY71-4(1) to CY71-4(32), and CY71-5(1) to CY71-5(8),
X82 to X85, L81, b81, R81, and R85 may respectively be understood by referring to the descriptions of X82 to X85, L81, b81, R81, and R85 provided herein,
X86 may be a single bond, O, S, N(R86), B(R86), C(R86a)(R86b), or Si(R86a)(R86),
X87 may be a single bond, O, S, N(R87), B(R87), C(R87a)(R87b), or Si(R87a)(R87b),
in Formulae CY71-1 (1) to CY71-1 (8) and CY71-4(1) to CY71-4(32), X86 and X87 may not be a single bond at the same time,
X88 may be a single bond, O, S, N(R88), B(R88), C(R88a)(R88b), or Si(R88a)(R88b),
X89 may be a single bond, O, S, N(R89), B(R89), C(R89a)(R89b), or Si(R89a)(R89b),
in Formulae CY71-2(1) to CY71-2(8), CY71-3(1) to CY71-3(32), and CY71-5(1) to CY71-5(8), X88 and X89 may not be a single bond at the same time, and
R86 to R89, R86a, R86b, R87a, R87b, R88a, R88b, R89a, and R89b may each be understood by referring to the description of R81 provided herein.
In some embodiments, the first compound (the organometallic compound represented by Formula 1) may include (e.g., may be) at least one of Compounds D1 to D315, at least one of Compounds 1 to 120, or any combination thereof:
In one or more embodiments, the second compound may include (e.g., may be) at least one of Compounds ETH1 to ETH84:
In one or more embodiments, the third compound may include (e.g., may be) at least one of Compounds HTH1 to HTH52:
In one or more embodiments, the fourth compound may include (e.g., may be) at least one of Compounds DFD1 to DFD14:
In the Compounds, “Ph” represents a phenyl group, “D5” represents substitution with five deuterium atoms, and “D4” represents substitution with four deuterium atoms. In some embodiments the group represented by
may be identical to the group represented by
In some embodiments, the light-emitting device may satisfy at least one of Conditions 1 to 4:
LUMO energy level (eV) of the third compound>LUMO energy level (eV) of the first compound, Condition 1
LUMO energy level (eV) of the first compound>LUMO energy level (eV) of the second compound, Condition 2
HOMO energy level (eV) of the first compound>HOMO energy level (eV) of the third compound, and Condition 3
HOMO energy level (eV) of the third compound>HOMO energy level (eV) of the second compound. Condition 4
The HOMO and LUMO energy levels of the first compound, the second compound, and the third compound may each be a negative value, and the HOMO and LUMO energy levels may be actual measurement value according to the methods described in Evaluation Example 1 provided herein.
In one or more embodiments, the absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be about 0.1 eV or higher and about 1.0 eV or lower, the absolute value of a difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be about 0.1 eV or higher and about 1.0 eV or lower, the absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be 1.25 eV or lower (e.g., about 1.25 eV or lower and about 0.2 eV or higher), and the absolute value of a difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be 1.25 eV or lower (e.g., about 1.25 eV or lower and about 0.2 eV or higher).
When the relationships between LUMO energy level and HOMO energy level satisfy the conditions as described above, the balance between holes and electrons injected into the emission layer can be made.
The light-emitting device may have a structure of a first embodiment or a second embodiment:
According to the first embodiment, the first compound may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host, the first compound may be different from the host, and the emission layer may emit phosphorescent light or fluorescent light emitted from the first compound. According to the first embodiment, the first compound may be a dopant or an emitter. In some embodiments, the first compound may be a phosphorescent dopant or a phosphorescent emitter.
Phosphorescent light or fluorescent light emitted from the first compound may be blue light.
The emission layer may further include an ancillary dopant. The ancillary dopant may serve to improve luminescence efficiency from the first compound by effectively (or suitably) transferring energy to a dopant or the first compound as an emitter.
The ancillary dopant may be different from the first compound and the host.
In some embodiments, the ancillary dopant may be a delayed fluorescence-emitting compound.
In some embodiments, the ancillary dopant may be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
According to the second embodiment, the first compound may be included in an emission layer in an interlayer of a light-emitting device, wherein the emission layer may further include a host and a dopant, the first compound may be different from the host and from the dopant, and the emission layer may emit phosphorescent light or fluorescent light (e.g., delayed fluorescent light) emitted from the dopant.
For example, the first compound in the second embodiment may serve as an ancillary dopant that transfers energy to a dopant (or an emitter), not as a dopant (or an emitter) itself.
In some embodiments, the first compound in the second embodiment may serve as an emitter and as an ancillary dopant that transfers energy to a dopant (or an emitter).
For example, phosphorescent light or fluorescent light emitted from the dopant (or the emitter) in the second embodiment may be blue phosphorescent light or blue fluorescent light (e.g., blue delayed fluorescent light).
The dopant (or the emitter) in the second embodiment may be a phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1, the organometallic compound represented by Formula 401, or any combination thereof) or a fluorescent dopant material (e.g, the compound represented by Formula 501, the compound represented by Formula 502, the compound represented by Formula 503, or any combination thereof).
In the first embodiment and the second embodiment, the blue light may be blue light having a maximum emission wavelength in a range of about 390 nanometers (nm) to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
The ancillary dopant in the first embodiment may include, e.g. the fourth compound represented by Formula 502 or Formula 503.
The host in the first embodiment and the second embodiment may be any suitable host material (e.g., the compound represented by Formula 301, the compound represented by 301-1, the compound represented by Formula 301-2, or any combination thereof).
In some embodiments, the host in the first embodiment and the second embodiment may be the second compound, the third compound, or any combination thereof.
In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside a first electrode or a second capping layer located outside a second electrode, and at least one of the first capping layer or the second capping layer may include the organometallic compound represented by Formula 1. The first capping layer and the second capping layer may respectively be understood by referring to the descriptions of the first capping layer and the second capping layer provided herein.
In some embodiments, the light-emitting device may include:
a first capping layer located outside the first electrode and including the organometallic compound represented by Formula 1;
a second capping layer located outside the second electrode and including the organometallic compound represented by Formula 1; or
the first capping layer and the second capping layer.
The expression that an “(interlayer and/or a capping layer) includes at least one organometallic compound represented by Formula 1” as used herein may be construed as meaning that the “(interlayer and/or the capping layer) may include one organometallic compound of Formula 1 or two or more different organometallic compounds of Formula 1”.
For example, the interlayer and/or the capping layer may include Compound D1 only as the organometallic compound. In this embodiment, Compound D1 may be included in the emission layer of the light-emitting device. In some embodiments, Compounds D1 and D2 may be included in the interlayer as organometallic compounds. In this embodiment, Compounds D1 and D2 may be included in the same layer (for example, both Compounds D1 and D2 may be included in an emission layer) or in different layers (for example, Compound D1 may be included in an emission layer, and Compound D2 may be included in an electron transport region).
The term “interlayer” as used herein refers to a single layer and/or a plurality of all layers located between a first electrode and a second electrode in a light-emitting device.
According to one or more embodiments, an electronic apparatus may include the light-emitting device. The electronic apparatus may further include a thin-film transistor. In some embodiments, the electronic apparatus may further include a thin-film transistor including a source electrode and drain electrode, and a first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. The electronic apparatus may further include a color filter, a color-conversion layer, a touchscreen layer, a polarization layer, or any combination thereof. The electronic apparatus may be understood by referring to the description of the electronic apparatus provided herein.
According to one or more embodiments, an organometallic compound may be represented by Formula 1, wherein Formula 1 may be understood by referring to the description of Formula 1 provided herein.
In the organometallic compound represented by Formula 1, the sum of a1 to a4 may be 1 or greater, and at least one of *-(L1)b1-(R1)c1(s) in the number of a1, at least one of R2(s) in the number of a2, at least one of R3(s) in the number of a3, at least one of R4(s) in the number of a4, or any combination thereof may each independently be the group represented by Formula 1-1 or the group represented by Formula 1-2:
For example, the organometallic compound represented by Formula 1 may include the group represented by Formula 1-1 and/or the group represented by Formula 1-2.
A moiety represented by ring CY7 in Formulae 1-1 and 1-2, a moiety represented by ring CY8 in Formula 1-1, and R8 and R9 in Formula 1-2 may each have a high triplet energy level (e.g., a triplet energy level as high as 0.01 eV). Accordingly, in Formula 1, energy transfer by metal to ligand charge transfer, and energy transfer by intramolecular through-space charge transfer, may both be activated. In addition, Formulae 1-1 and 1-2 may each have structural rigidity due to ring CY7.
Therefore, a light-emitting device (e.g., an organic light-emitting device) including the organometallic compound represented by Formula 1 (or the first compound represented by Formula 1) may have high color purity, high luminescence efficiency, low driving voltage, and long lifespan characteristics.
In one or more embodiments, the organometallic compound represented by Formula 1 may emit blue light. In some embodiments, the organometallic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in a range of about 390 nm to about 500 nm, about 410 nm to about 490 nm, about 430 nm to about 480 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
In one or more embodiments, the organometallic compound represented by Formula 1 may have a color purity of a bottom emission CIEx coordinate in a range of about 0.12 to about 0.15, or about 0.13 to about 0.14, and a bottom emission CIEy coordinate in a range of about 0.06 to about 0.25, about 0.10 to about 0.20, or about 0.13 to about 0.20.
Methods of synthesizing the organometallic compound represented by Formula 1 may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and Examples described herein.
hereinafter, the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10 according to one or more embodiments will be described in connection with
In
The first electrode 110 may be formed by depositing or sputtering, onto the substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, a high work function material that may easily (or suitably) inject holes may be used as a material for a first electrode 110.
The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combinations thereof. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be used as a material for forming the first electrode 110.
The first electrode 110 may have a single-layered structure including (e.g., consisting of) a single layer or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO.
The interlayer 130 may be on the first electrode 110. The interlayer 130 may include 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 metal-containing compounds such as organometallic compounds, inorganic materials such as quantum dots, and/or the like, in addition to various organic materials.
The interlayer 130 may include: i) at least two emitting units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge-generation layer located between the at least two emitting units. When the interlayer 130 includes the at least two emitting units and the charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.
The hole transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The hole transport region may include a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, an electron blocking layer (EBL), or any combination thereof.
For example, the hole transport region may have a multi-layered structure, e.g., a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein layers of each structure are sequentially stacked on the first electrode 110 in each stated order.
The hole transport region may include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof:
wherein, in Formulae 201 and 202,
L201 to L204 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
L205 may be *—O—*′, *—S—*′, *—N(Q201)—*′, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C2-C20 alkenylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xa1 to xa4 may each independently be an integer from 0 to 5,
xa5 may be an integer from 1 to 10,
R201 to R204 and Q201 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R201 and R202 may optionally be bound to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group (e.g., a carbazole group and/or the like) that is unsubstituted or OC substituted with at least one R10a (e.g., Compound HT16 described herein),
R203 and R204 may optionally be bound to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a, and
na1 may be an integer from 1 to 4.
In some embodiments, Formulae 201 and 202 may each include at least one of groups represented by Formulae CY201 to CY217:
wherein, in Formulae CY201 to CY217, R10b and R10c may each be understood by referring to the descriptions of R10a, ring CY201 to ring CY204 may each independently be a C3-C20 carbocyclic group or a C1-C20 heterocyclic group, and hydrogen atoms in Formulae CY201 to CY217 may each independently be unsubstituted or substituted with R10a.
In some embodiments, in Formulae CY201 to CY217, ring CY201 to ring CY204 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
In one or more embodiments, Formulae 201 and 202 may each include at least one of groups represented by Formula CY201 to CY203.
In one or more embodiments, Formula 201 may include at least one of groups represented by Formulae CY201 to CY203 and at least one of groups represented by Formulae CY204 to CY217.
In one or more embodiments, in Formula 201, xa1 may be 1, R201 may be a group represented by any one of Formulae CY201 to CY203, xa2 may be 0, and R202 may be a group represented by any one of Formulae CY204 to CY207.
In one or more embodiments, Formula 201 and 202 may each not include groups represented by Formulae CY201 to CY203.
In one or more embodiments, Formula 201 and 202 may each not include groups represented by Formulae CY201 to CY203, and include at least one of groups represented by Formulae CY204 to CY217.
In one or more embodiments, Formula 201 and 202 may each not include groups represented by Formulae CY201 to CY217.
In some embodiments, the hole transport region may include one selected from Compounds HT1 to HT44, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), and any combinations thereof:
The thickness of the hole transport region may be in a range of about 50 (Angstroms) Å to about 10,000 Å, and in some embodiments, 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, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and in some embodiments, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and in some embodiments, 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 any of their respective ranges, excellent (or improved) hole transport 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 according to the wavelength of light emitted by an emission layer. The electron blocking layer may reduce or eliminate the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may each independently include any of the aforementioned materials.
p-Dopant
The hole transport region may include a charge generating material, as well as the aforementioned materials, to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed (for example, as a single layer consisting of charge generating material) in the hole transport region.
The charge generating material may include, for example, a p-dopant.
In some embodiments, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.
In some embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, elements EL1 and EL2-containing compound, or any combination thereof.
Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
Examples of the cyano group-containing compound include HAT-CN, a compound represented by Formula 221, and the like:
wherein, in Formula 221,
R221 to R223 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, and
at least one of R221 to R223 may each independently be: a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each independently substituted with a cyano group; —F; —Cl; —Br; —I; a C1-C20 alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.
In the elements EL1 and EL2-containing compound, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.
Non-limiting examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (To), 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), and/or the like); post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), and/or the like); a lanthanide metal (e.g., 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), and/or the like); and the like.
Non-limiting examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
Non-limiting examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, and the like), and the like.
For example, the elements EL1 and EL2-containing compound may include a metal oxide, a metal halide (e.g., metal fluoride, metal chloride, metal bromide, metal iodide, and/or the like), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, and/or the like), a metal telluride, or any combination thereof.
Non-limiting examples of the metal oxide may include tungsten oxide (e.g., WO, W2O3, WO2, WO3, W2O5, and/or the like), vanadium oxide (e.g., VO, V2O3, VO2, V2O5, and/or the like), molybdenum oxide (MoO, Mo2O3, MoO2, MoO3, Mo2O5, and/or the like), rhenium oxide (e.g., ReO3, and/or the like), and the like.
Non-limiting examples of the metal halide may include alkali metal halide, alkaline earth metal halide, transition metal halide, post-transition metal halide, lanthanide metal halide, and the like.
Non-limiting 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, CsI, and the like.
Non-limiting examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, and the like.
Non-limiting examples of the transition metal halide may include titanium halide (e.g., TiF4, TiCl4, TiBr4, TiI4, and/or the like), zirconium halide (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, and/or the like), hafnium halide (e.g., HfF4, HfCl4, HfBr4, HfI4, and/or the like), vanadium halide (e.g., VF3, VCl3, VBr3, VI3, and/or the like), niobium halide (e.g., NbF3, NbCl3, NbBr3, NbI3, and/or the like), tantalum halide (e.g., TaF3, TaCl3, TaBr3, TaI3, and/or the like), chromium halide (e.g., CrF3, CrCl3, CrBr3, CrI3, and/or the like), molybdenum halide (e.g., MoF3, MoCl3, MoBr3, MoI3, and/or the like), tungsten halide (e.g., WF3, WCl3, WBr3, WI3, and/or the like), manganese halide (e.g., MnF2, MnCl2, MnBr2, MnI2, and/or the like), technetium halide (e.g., TcF2, TcCl2, TcBr2, TcI2, and/or the like), rhenium halide (e.g., ReF2, ReCl2, ReBr2, ReI2, and/or the like), iron halide (e.g., FeF2, FeCl2, FeBr2, FeI2, and/or the like), ruthenium halide (e.g., RuF2, RuCl2, RuBr2, RuI2, and/or the like), osmium halide (e.g., OsF2, OsCl2, OsBr2, OsI2, and/or the like), cobalt halide (e.g., CoF2, CoCl2, CoBr2, CoI2, and/or the like), rhodium halide (e.g., RhF2, RhCl2, RhBr2, RhI2, and/or the like), iridium halide (e.g., IrF2, IrCl2, IrBr2, IrI2, and/or the like), nickel halide (e.g., NiF2, NiCl2, NiBr2, NiI2, and/or the like), palladium halide (e.g., PdF2, PdCl2, PdBr2, PdI2, and/or the like), platinum halide (e.g., PtF2, PtCl2, PtBr2, PtI2, and/or the like), copper halide (e.g., CuF, CuCl, CuBr, CuI, and/or the like), silver halide (e.g., AgF, AgCl, AgBr, AgI, and/or the like), gold halide (e.g., AuF, AuCl, AuBr, AuI, and/or the like), and the like.
Non-limiting examples of the post-transition metal halide may include zinc halide (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, and/or the like), indium halide (e.g., InI3 and/or the like), tin halide (e.g., SnI2 and/or the like), and the like.
Non-limiting examples of the lanthanide metal halide may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
Non-limiting examples of the metalloid halide may include antimony halide (e.g., SbCl5 and/or the like) and the like.
Non-limiting examples of the metal telluride may include alkali metal telluride (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, and/or the like), alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, and/or the like), transition metal telluride (e.g., TiTe2, ZrTe2, FIfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, and/or the like), post-transition metal telluride (e.g., ZnTe and/or the like), lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, and/or the like), and the like.
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 one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer. The two or more layers may be in direct contact with each other. In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light-emitting material, a green light-emitting material, or a blue light-emitting material. The two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in the single layer may emit white light.
In some embodiments, the emission layer may include a host and a dopant (or an emitter). In some embodiments, the emission layer may further include an ancillary dopant that promotes energy transfer to a dopant (or an emitter), in addition to the host and the dopant (or the emitter). When the emission layer includes the dopant (or the emitter) and the ancillary dopant, the dopant (or the emitter) may be different from the ancillary dopant.
The first compound may serve as the dopant (or the emitter) or as the ancillary dopant.
The amount of the dopant (or the emitter) in the emission layer may be in a range of about 0.01 parts to about 15 parts by weight based on 100 parts by weight of the host.
The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.
The host in the emission layer may include the second compound, the third compound, or any combination thereof.
In some embodiments, the host may further include a compound represented by Formula 301:
[Ar301]xb11-[(L301)xb1-R301]xb21, Formula 301
wherein, in Formula 301,
Ar301 and L301 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xb11 may be 1,2, or 3,
xb1 may be an integer from 0 to 5,
R301 may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), or —P(═O)(Q301)(Q302),
xb21 may be an integer from 1 to 5, and
Q301 to Q303 may each be understood by referring to the description of Q1 provided herein.
In some embodiments, when xb11 in Formula 301 is 2 or greater, at least two Ar301(s) may be bound via a single bond.
In some embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
wherein, in Formulae 301-1 to 301-2,
ring A301 to ring A304 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
X301 may be O, S, N-[(L304)xb4-R304], C(R304)(R305), or Si(R304)(R305),
xb22 and xb23 may each independently be 0, 1, or 2,
L301, xb1, and R301 may respectively be understood by referring to the descriptions of L301, xb1, and R301 provided herein,
L302 to L304 may each be understood by referring to the description of L301 provided herein,
xb2 to xb4 may each be understood by referring to the description of xb1 provided herein, and
R302 to R305 and R311 to R314 may each be understood by referring to the description of R301 provided herein.
In some embodiments, the host may include an alkaline earth metal complex. For example, the host may include a Be complex (e.g., Compound H55), a Mg complex, a Zn complex, or any combination thereof.
In some embodiments, the host may include one of Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
In some embodiments, the host may include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
The host may include one type (or kind) of compound only, or two or more different types (or kinds) of compounds. As such, embodiments may be modified in various ways.
The emission layer may include the first compound described herein as a phosphorescent dopant.
In some embodiments, the emission layer may include the first compound, and when the first compound serves as an ancillary dopant, the emission layer may include a phosphorescent dopant.
The phosphorescent dopant may include at least one transition metal as a center 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 some embodiments, the phosphorescent dopant may include an organometallic complex represented by Formula 401:
wherein, in Formulae 401 and 402,
M may be transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
L401 may be a ligand represented by Formula 402, and xc1 may be 1,2, or 3, and when xc1 is 2 or greater, at least two L401(s) may be identical to or different from each other,
L402 may be an organic ligand, and xc2 may be an integer from 0 to 4, and when xc2 is 2 or greater, at least two L402(s) may be identical to or different from each other,
X401 and X402 may each independently be nitrogen or carbon,
ring A401 and ring A402 may each independently be a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
T401 may be a single bond, *—C(═O)—*′, *—N(Q411)-*′, *—C(Q411)(Q412)-*′, *—C(Q411)═C(Q412)-*′, *—C(Q411)=*′, or *═C=*′,
X403 and X404 may each independently be a chemical bond (e.g., a covalent bond or a coordinate bond), O, S, N(Q413), B(Q413), P(Q413), C(Q413)(Q414), or Si(Q413)(Q414),
Q411 to Q414 may each be understood by referring to the description of Q1 provided herein,
R401 and R402 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group unsubstituted or substituted with at least one R10a, a C1-C20 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q401)(Q402)(Q403), —N(Q401)(Q402), —B(Q401)(Q402), —C(═O)(Q401), —S(═O)2(Q401), or —P(═O)(Q401)(Q402),
Q401 to Q403 may each be understood by referring to the description of Q1 provided herein,
xc11 and xc12 may each independently be an integer from 0 to 10, and
* and *′ in Formula 402 each indicate a binding site to M in Formula 401.
In one or more embodiments, in Formula 402, i) X401 may be nitrogen, and X402 may be carbon, or ii) X401 and X402 may both be nitrogen.
In one or more embodiments, when xc1 in Formula 401 is 2 or greater, two ring A401(s) of at least two L401(s) may optionally be bound via T402 as a linking group, and/or two ring A402(s) may optionally be bound via T403 as a linking group (see e.g., Compounds PD1 to PD4 and PD7). T402 and T403 may each be understood by referring to the description of T401 provided herein.
L402 in Formula 401 may be any suitable organic ligand. For example, L402 may be a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), —C(═O), an isonitrile group, —CN, or a phosphorus group (e.g., a phosphine group and/or a phosphite group).
The phosphorescent dopant may be, for example, one of Compounds PD1 to PD25 or any combination thereof:
In some embodiments, the emission layer may include the first compound, and when the first compound serves as an ancillary dopant, the emission layer may include a fluorescent dopant.
In some embodiments, the emission layer may include the first compound, and when the first compound serves as a phosphorescent dopant, the emission layer may include an ancillary dopant.
The fluorescent dopant and the ancillary dopant may each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
In some embodiments, the fluorescent dopant and the ancillary dopant may each independently include the compound represented by Formula 501:
wherein, in Formula 501,
Ar501, L501 to L503, R501, and R502 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xd1 to xd3 may each independently be 0, 1, 2, or 3, and
xd4 may be 1,2, 3, 4, 5, or 6.
In some embodiments, in Formula 501, Ar501 may include a condensed ring group (e.g., an anthracene group, a chrysene group, and/or a pyrene group), in which at least three monocyclic groups are condensed.
In some embodiments, xd4 in Formula 501 may be 2.
In some embodiments, the fluorescent dopant and the ancillary dopant may each independently include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
In some embodiments, the fluorescent dopant and the ancillary dopant may each independently include the fourth compound represented by Formula 502 or Formula 503.
The electron transport region may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or an electron injection layer.
In some embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein layers of each structure are sequentially stacked on the emission layer in each stated order.
The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, and/or an 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 some embodiments, the electron transport region may include a compound represented by Formula 601:
[Ar601]xe11-[(L601)xe1-R601]xe21, Formula 601
wherein, in Formula 601,
Ar601 and L601 may each independently be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xe11 may be 1,2, or 3,
xe1 may be 0, 1, 2, 3, 4, or 5,
R601 may be a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, —Si(Q601)(Q602)(Q603), —C(═O)(Q601), —S(═O)2(Q601), or —P(═O)(Q601)(Q602),
Q601 to Q603 may each be understood by referring to the description of Q1 provided herein,
xe21 may be 1, 2, 3, 4, or 5, and
at least one of Ar601, L601, and R601 may each independently be a π electron-deficient nitrogen-containing C1-C60 cyclic group unsubstituted or substituted with at least one R10a.
In some embodiments, when xe11 in Formula 601 is 2 or greater, at least two Ar601(s) may be bound via a single bond.
In some embodiments, in Formula 601, Ar601 may be a substituted or unsubstituted anthracene group.
In some embodiments, the electron transport region may include a compound represented by Formula 601-1:
wherein, in Formula 601-1,
X614 may be N or C(R614), X615 may be N or C(R615), X616 may be N or C(R616), at least one selected from X614 to X616 may be N,
L611 to L613 may each be understood by referring to the description of L601 provided herein,
xe611 to xe613 may each be understood by referring to the description of xe1 provided herein,
R611 to R613 may each be understood by referring to the description of R601 provided herein, and
R614 to R616 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a.
For example, in Formulae 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
The electron transport region may include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAIq, TAZ, NTAZ, or any combination thereof:
The thickness of the electron transport region may be in a range of about 160 Å to about 5,000 Å, and in some embodiments, about 100 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 thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport layer are each within their respective ranges, excellent (or improved) electron transport 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 lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, or a cesium (Cs) ion. A metal ion of the alkaline earth metal complex may be a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, or a barium (Ba) ion. Ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may each independently be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
For example, the metal-containing material may include a Li complex. The Li complex may include, e.g., Compound ET-D1 (LiQ) and/or Compound ET-D2:
The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
The electron injection layer may have i) a single-layered structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of 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 be Li, Na, K, Rb, Cs or any combination thereof. The alkaline earth metal may be Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may be 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 respectively be oxides, halides (e.g., fluorides, chlorides, bromides, and/or iodines), tellurides, or any combination thereof of the alkali metal, the alkaline earth metal, and the rare earth metal.
The alkali metal-containing compound may be selected from 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 alkaline earth-metal oxides (such as BaO, SrO, CaO, BaxSr1-xO (wherein x is a real number satisfying 0<x<1), and/or BaxCa1-xO (wherein x is a real number satisfying 0<x<1)). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In some embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Non-limiting 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, Lu2Te3, and the like.
The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may respectively include: i) one of metal ions of the alkali metal, alkaline earth metal, and rare earth metal described above and ii) a ligand bound to the metal ion, e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, 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 some embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
In some embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In some embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and/or the like.
When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of these ranges, excellent (or improved) electron injection characteristics may be obtained without a substantial increase in driving voltage.
The second electrode 150 may be on the interlayer 130. In one or more embodiments, the second electrode 150 may be a cathode, that is an electron injection electrode. In this embodiment, a material for forming the second electrode 150 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or any combination thereof.
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 multi-layered structure including two or more layers.
A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. In some embodiments, 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.
In the light-emitting device 10, light emitted from the emission layer in the interlayer 130 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer to the outside. In the light-emitting device 10, light emitted from the emission layer in the interlayer 130 may pass through the second electrode 150 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer to the outside.
The first capping layer and the second capping layer may improve the external luminescence efficiency based on the principle of constructive interference. Accordingly, the optical extraction efficiency of the light-emitting device 10 may be increased, thus improving luminescence efficiency of the light-emitting device 10.
The first capping layer and the second capping layer may each include a material having a refractive index of 1.6 or higher (at 589 nm).
The first capping layer and the second capping layer may each independently be a capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
At least one of the first capping layer and the second capping layer may each independently include one or more selected from carbocyclic compounds, heterocyclic compounds, amine group-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, and any combinations thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In some embodiments, at least one of the first capping layer and the second capping layer may each independently include an amine group-containing compound.
In some embodiments, at least one of the first capping layer and the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
In one or more embodiments, at least one of the first capping layer and the second capping layer may each independently include one of Compounds FIT28 to FIT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:
The light-emitting device may be included in various suitable electronic apparatuses. In some embodiments, an electronic apparatus including the light-emitting device may be an emission apparatus or an authentication apparatus.
The electronic apparatus (e.g., an emission 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 disposed on at least one traveling direction of light emitted from the light-emitting device. For example, light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be understood by referring to the description thereof provided herein. In some embodiments, the color-conversion layer may include quantum dots.
The electronic apparatus may include a first substrate. The first substrate may include a plurality of sub-pixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the plurality of sub-pixel areas, and the color-conversion layer may include a plurality of color-conversion areas respectively corresponding to the plurality of sub-pixel areas.
A pixel defining film may be located between the plurality of sub-pixel areas to define each sub-pixel area.
The color filter may further include a plurality of color filter areas and light-blocking patterns between the plurality of color filter areas, and the color-conversion layer may further include a plurality of color-conversion areas and light-blocking patterns between the plurality of color-conversion areas.
The plurality of color filter areas (and/or a plurality of color-conversion areas) may include: a first area to emit first color light; a second area to emit second color light; and/or a third area to emit third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. In some embodiments, 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 some embodiments, the plurality of color filter areas (and/or the plurality of color-conversion areas) may each include quantum dots. In some embodiments, the first area may include red quantum dots, the second area may include green quantum dots, and the third area may not include a quantum dot. The quantum dot may be understood by referring to the description of the quantum dot provided herein. The first area, the second area, and/or the third area may each further include an emitter.
In some embodiments, the light-emitting device may emit first light, the first area may absorb the first light to emit 1-1 color light, the second area may absorb the first light to emit 2-1 color light, and the third area may absorb the first light to emit 3-1 color light. In this embodiment, the 1-1 color light, the 2-1 color light, and the 3-1 color light may each have a different maximum emission wavelength. In some embodiments, the first light may be blue light, the 1-1 color light may be red light, the 2-1 color light may be green light, and the 3-1 color light may be blue light.
The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode or the drain electrode may be electrically connected to one of the first electrode or the second electrode of the light-emitting device.
The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.
The active layer may include a crystalline silicon, an amorphous silicon, an organic semiconductor, and/or an oxide semiconductor.
The electronic apparatus may further include an encapsulation unit for sealing the light-emitting device. The encapsulation unit may be located between the color filter and/or the color-conversion layer and the light-emitting device. The encapsulation unit may allow light to pass to the outside from the light-emitting device and may prevent or reduce the permeation of the air and moisture into the light-emitting device at the same time. The encapsulation unit may be a sealing substrate including a transparent glass and/or a plastic substrate. The encapsulation unit may be a thin-film encapsulating layer including at least one of an organic layer or an inorganic layer. When the encapsulation unit is a thin film encapsulating layer, the electronic apparatus may be flexible.
In addition to the color filter and/or the color-conversion layer, one or more functional layers may be disposed on the encapsulation unit, depending on the use of an electronic apparatus. Examples of the functional layer may include a touch screen layer, a polarization layer, and the like. The touch screen layer may be a resistive touch screen layer, a capacitive touch screen layer, or an infrared beam touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual according biometric information (e.g., a fingertip, a pupil, and/or the like).
The authentication apparatus may further include a biometric information collecting unit, in addition to the light-emitting device described above.
The electronic apparatus may be applicable to various suitable displays, an optical source, lighting, a personal computer (e.g., a mobile personal computer), a cellphone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, an endoscope display device), a fish finder, various measurement devices, gauges (e.g., gauges of an automobile, an airplane, a ship), a projector, and/or the like.
An emission apparatus in
The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be 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 thin-film transistor may be on the buffer layer 210. The thin-film transistor may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
The active layer 220 may include an inorganic semiconductor (such as silicon and/or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source area, a drain area and a channel area.
A gate insulating film 230 for insulating the active layer 220 and the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.
An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to provide insulation therebetween.
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 be formed to expose the source area and the drain area of the active layer 220, and the source electrode 260 and the drain electrode 270 may be adjacent to the exposed source area and the exposed drain area of the active layer 220.
Such a thin-film transistor may be electrically connected to a light-emitting device to drive the light-emitting device, and may be protected 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 may be 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 on the passivation layer 280. The passivation layer 280 may not fully cover the drain electrode 270, and may expose a specific (or set) area of the drain electrode 270, and the first electrode 110 may be disposed to connect to (e.g., to contact) the exposed area of the drain electrode 270.
A pixel-defining film 290 may be on the first electrode 110. The pixel-defining film 290 may expose a specific (or set) area of the first electrode 110, and the interlayer 130 may be formed in the exposed area. The pixel-defining film 290 may be a polyimide or polyacryl organic film. In one or more embodiments, some of the upper layers of the interlayer 130 may extend to the upper portion of the pixel-defining film 290 and may be disposed 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 formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
The encapsulation unit 300 may be on the capping layer 170. The encapsulation unit 300 may be on the light-emitting device to protect a light-emitting device from moisture and/or oxygen. The encapsulation unit 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, polyoxy methylene, polyarylate, hexamethyl disiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy resin (e.g., aliphatic glycidyl ether (AGE) and/or the like), or any combination thereof; or a combination of the inorganic film and the organic film.
The emission apparatus shown in
The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a specific 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 the layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region are each independently formed by vacuum deposition, the vacuum deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C. at a vacuum degree in a range of about 10−8 torr to about 10−3 torr, and at a deposition rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.
The term “C3-C60 carbocyclic group” as used herein refers to a cyclic group consisting of carbon atoms only as ring-forming atoms, and having 3 to 60 ring-forming carbon atoms. The term “C1-C60 heterocyclic group” as used herein refers to a cyclic group having 1 to 60 ring-forming carbon atoms, in addition to a heteroatom other than a carbon atom. The C3-C60 carbocyclic group and the C1-C60 heterocyclic group may each independently be a monocyclic group consisting of one ring or a polycyclic group in which at least two rings are condensed. For example, the total number of ring-forming atoms in the C1-C60 heterocyclic group may be in a range of 1 to 60.
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” refers to a cyclic group having 3 to 60 carbon atoms and not including *—N=*′ as a ring-forming moiety. The term “TT electron-deficient nitrogen-containing C1-C60 cyclic group” as used herein refers to a heterocyclic group having 1 to 60 carbon atoms and *—N=*′ as a ring-forming moiety.
In some embodiments,
the C3-C60 carbocyclic group may be i) a T1 group or ii) a group in which at least two T1 groups are condensed (for example, the C3-C60 carbocyclic group may be a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, or an indenoanthracene group),
the C1-C60 heterocyclic group may be i) a T2 group, ii) a group in which at least two T2 groups are condensed, or iii) a group in which at least one T2 group is condensed with at least one T1 group (for example, the C1-C60 heterocyclic group may be a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonapthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like),
the π electron-rich C3-C60 cyclic group may be i) a T1 group, ii) a condensed group in which at least two T1 groups are condensed, iii) a T3 group, iv) a condensed group in which at least two T3 groups are condensed, or v) a condensed group in which at least one T3 group is condensed with at least one T1 group (for example, the π electron-rich C3-C60 cyclic group may be a C3-C60 carbocyclic group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonapthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, and/or the like), and
the π electron-deficient nitrogen-containing C1-C60 cyclic group may be i) a T4 group, ii) a group in which at least twos T4 groups are condensed, iii) a group in which at least one T4 group is condensed with at least one T1 group, iv) a group in which at least one T4 group is condensed with at least one T3 group, or v) a group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed (for example, he π electron-deficient nitrogen-containing C1-C60 cyclic group may be a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like),
wherein the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group,
the T2 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group,
the T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and
the T4 group may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.
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 may be a group condensed with any suitable cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a quadvalent group, and/or the like), depending on the structure of the formula to which the term is applied. For example, a “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, and this may be understood by one of ordinary skill in the art, depending on the structure of the formula including the “benzene group”.
Examples of the monovalent C3-C60 carbocyclic group and the 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. Examples of the divalent C3-C60 carbocyclic group and the divalent C1-C60 heterocyclic group may include a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 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 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 having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, an n-propyl group, an iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl 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 the same structure as the C1-C60 alkyl group.
The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle and/or at either terminus of the C2-C60 alkyl group. Non-limiting 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 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 in the middle and/or at either terminus of the C2-C60 alkyl group. Non-limiting 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 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 a C1-C1 alkyl group). Non-limiting 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 monocyclic group including 3 to 10 carbon atoms. Non-limiting examples of the C3-C10 cycloalkyl group as used herein include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl (bicyclo[2.2.1]heptyl) group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and/or a bicyclo[2.2.2]octyl group). The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
The term “C1-C10 heterocycloalkyl group” as used herein refers to a monovalent cyclic group including at least one heteroatom, other than carbon atoms, as a ring-forming atom, and having 1 to 10 carbon atoms. Non-limiting 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 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 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and is not aromatic. Non-limiting 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 the same structure as the C3-C10 cycloalkenyl group.
The term “C1-C10 heterocycloalkenyl group” as used herein refers to a monovalent cyclic group including at least one heteroatom, other than carbon atoms, as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting 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 the same structure as the C1-C10 heterocycloalkyl group.
The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 6 carbon atoms. The term “C6-C60 arylene group” as used herein refers to a divalent group having the same structure as the C6-C60 aryl group. Non-limiting 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 independently include two or more rings, the respective rings may be fused.
The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system further including at least one heteroatom, other than carbon atoms, 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 the same structure as the C1-C60 heteroaryl group. Non-limiting 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 independently include two or more rings, the respective rings may be fused.
The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more rings condensed and only carbon atoms as ring forming atoms (e.g., 8 to 60 carbon atoms), wherein the entire molecular structure (as a whole) is non-aromatic. Non-limiting 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 indenoanthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.
The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and at least one heteroatom, other than carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, wherein the entire molecular structure (as a whole) is non-aromatic. Non-limiting 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 naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzooxadiazolyl 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 the monovalent non-aromatic condensed heteropolycyclic group.
The term “C6-C60 aryloxy group” as used herein refers to a monovalent group represented by —OA102 (wherein A102 is the C6-C60 aryl group). The term “C6-C60 arylthio group” as used herein refers to a monovalent group represented by —SA103 (wherein A103 is the C6-C60 aryl group).
The term “R10a” as used herein may be:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each independently unsubstituted or substituted with deuterium, —F, —C1, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32).
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 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each independently 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, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or any combination thereof.
The term “heteroatom” as used herein refers to any atom other than a carbon atom. Non-limiting examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
“Ph” used herein represents a phenyl group, “Me” used herein represents a methyl group, “Et” used herein represents an ethyl group, “tert-Bu” or “But” used herein represents a tert-butyl group, “OMe” used herein represents a methoxy group, and “D” as used herein represents deuterium.
The term “biphenyl group” as used herein refers to a phenyl group substituted with at least one phenyl group. The “biphenyl group” belongs to “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 at least one biphenyl group. The “terphenyl group” belongs to “a substituted phenyl group” having a “C6-C60 aryl group substituted with a C6-C60 aryl group” as a substituent.
The symbols *, *′ and *″ as used herein, unless defined otherwise, refer to a binding site to an adjacent atom in a corresponding formula.
Hereinafter, compounds and a light-emitting device according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used in terms of molar equivalents.
25.0 g (70.8 mmol) of 9-(4-bromopyridin-2-yl)-2-methoxy-9H-carbazole was mixed with 700 mL of tetrahydrofuran, the temperature was lowered to −78° C., and 39 mL of n-BuLi solution (2.0 molar (M) in hexane) was added thereto, followed by stirring for 1 hour at the same temperature. Then, 21.3 g (141.6 mmol) of 2-adamantanone was added thereto, and the temperature was raised to room temperature, followed by stirring for 24 hours. Once the reaction was complete, a NaHCO3 solution was added thereto, and an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 22.3 g (52.5 mmol) of Intermediate D6-1.
22.3 g (52.5 mmol) of Intermediate D6-1 and 21.0 g (157.5 mmol) of AlCl3 were stirred for 24 hours at room temperature with excess benzene in a nitrogen atmosphere. Once the reaction was complete, a NaHCO3 solution was added thereto for neutralization, and an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 20.0 g (41.2 mmol) of Intermediate D6-2.
20.2 g (41.7 mmol) of Intermediate D6-2 was suspended in an excess hydrobromic acid solution, followed by raising the temperature to 110° C. and stirring for 24 hours. Once the reaction was complete, the temperature was lowered to room temperature, and a proper amount of NaHCO3 was added thereto for neutralization. Then, 300 mL of distilled water was added thereto, and an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed using saturated sodium chloride aqueous solution, followed by drying using MgSO4. The resulting product was subjected to column chromatography to thereby obtain 18.9 g (39.5 mmol) of Intermediate D6-3.
15.4 g (32.7 mmol) of Intermediate D6-3, 8.2 g (34.6 mmol) of 1,3-dibromobenzene, 13.9 g (65.4 mmol, 2.0 eq.) of K3PO4, 0.6 g (3.3 mmol, 0.1 eq.) of CuI, and 1.3 g (3.3 mmol) of di([1,1′-biphenyl]-2-yl)oxalamide were added to a reaction vessel, and the mixture was suspended in 80 mL of dimethyl sulfoxide, followed by raising the temperature to 160° C. and stirring for 12 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 16.5 g (26.3 mmol) of Intermediate D6-4.
23.8 g (38.1 mmol) of Intermediate D6-4, 15.8 g (45.7 mmol) of N1-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d10)benzene-1,2-diamine, 0.4 g (0.76 mmol, 0.02 eq.) of Pd2(dba)3, 0.6 g (1.52 mmol, 0.04 eq.) of SPhos, and 4.8 g (49.5 mmol, 1.6 eq.) of NaOtBu were added to a reaction vessel, and the mixture was suspended in 100 mL of toluene (0.1 M), followed by raising the temperature to 120° C. and stirring for 4 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 23.6 g (26.5 mmol) of Intermediate D6-5.
23.2 g (26.0 mmol) of Intermediate D6-5, 216 ml_(1.3 mol, 50.0 eq.) of triethyl orthoformate, and 0.9 ml_(31.2 mmol, 1.2 eq.) of HCl (37%) were added to a reaction vessel, and the temperature was raised to 80° C. and stirred for 12 hours. Once the reaction was complete, the temperature was cooled to room temperature, and the resulting solid was filtered and washed using ether. Then, the washed solid was dried to thereby obtain 22.5 g (23.4 mmol) of Intermediate D6-6.
21.1 g (22.5 mmol) of Intermediate D6-6 and 11.0 g (67.5 mmol, 3.0 eq.) of NH4PF6 were added to a reaction vessel, and the mixture was suspended in a mixed solution of 100 mL of methyl alcohol and 50 mL of water (at a volumetric ratio of 2:1), followed by stirring at room temperature for 24 hours. Once the reaction was complete, the resulting solid was filtered and washed using ether. Then, the washed solid was dried to thereby obtain 26.0 g (16.8 mmol) of Intermediate D6-7.
16.5 g (15.8 mmol) of Intermediate D6-7, 6.2 g (16.7 mmol, 1.1 eq.) of dichloro(1,5-cyclooctadiene)platinum, and 3.9 g (47.4 mmol, 3.0 eq.) of NaOAc were suspended in 300 mL of 1,4-dioxane (0.025 M), and the temperature was raised to 110° C., followed by stirring for 72 hours. Once the reaction was complete, the temperature was cooled to room temperature, 250 mL of distilled water was added thereto, and an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed using NaCl aqueous solution and dried using MgSO4. The resulting product was subjected to column chromatography to thereby obtain 5.5 g (5.1 mmol) of Compound D6.
22.3 g (52.5 mmol) of Intermediate D6-1, 21.0 g (157.5 mmol) of AlCl3, and 4a,8a-azaboranaphthalene (1.0 eq.) were stirred for 24 hours at a temperature of 40° C. with excess dichloromethane in a nitrogen atmosphere. Once the reaction was complete, a NaHCO3 solution was added thereto for neutralization, and an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain Intermediate D12-2.
Intermediate D12-3 was obtained in substantially the same manner as in Synthesis of Intermediate D6-3 in Synthesis Example 1, except that Intermediate D12-2 was used instead of Intermediate D6-2.
Intermediate D12-4 was obtained in substantially the same manner as in Synthesis of Intermediate D6-4 in Synthesis Example 1, except that Intermediate D12-3 was used instead of Intermediate D6-3.
Intermediate D12-5 was obtained in substantially the same manner as in Synthesis of Intermediate D6-5 in Synthesis Example 1, except that Intermediate D12-4 was used instead of Intermediate D6-4.
Intermediate D12-6 was obtained in substantially the same manner as in Synthesis of Intermediate D6-6 in Synthesis Example 1, except that Intermediate D12-5 was used instead of Intermediate D6-5.
Intermediate D12-7 was obtained in substantially the same manner as in Synthesis of Intermediate D6-7 in Synthesis Example 1, except that Intermediate D12-6 was used instead of Intermediate D6-6.
5.60 g (4.90 mmol) of Compound D12 was obtained in substantially the same manner as in Synthesis of Compound D6 in Synthesis Example 1, except that Intermediate D12-7 was used instead of Intermediate D6-7.
Intermediate D27-4 was synthesized in substantially the same manner as in Synthesis of Intermediate D12-4 in Synthesis Example 2, except that 1,3-dibromo-5-(tert-butyl)benzene was used instead of 1,3-dibromobenzene.
Intermediate D27-5 was obtained in substantially the same manner as in Synthesis of Intermediate D12-5 in Synthesis Example 2, except that Intermediate D27-4 was used instead of Intermediate D12-4.
Intermediate D27-6 was obtained in substantially the same manner as in Synthesis of Intermediate D12-6 in Synthesis Example 2, except that Intermediate D27-5 was used instead of Intermediate D12-5.
Intermediate D27-7 was obtained in substantially the same manner as in Synthesis of Intermediate D12-7 in Synthesis Example 2, except that Intermediate D27-6 was used instead of Intermediate D12-6.
5.88 g (4.90 mmol) of Compound D27 was obtained in substantially the same manner as in Synthesis of Compound D12 in Synthesis Example 2, except that Intermediate D27-7 was used instead of Intermediate D12-7.
Intermediate D81-4 was synthesized in substantially the same manner as in Synthesis of Intermediate D6-4 in Synthesis Example 1, except that 3,5-dibromo-6′-phenyl-1,1′:2′,1″-terphenyl was used instead of 1,3-dibromobenzene.
Intermediate D81-5 was obtained in substantially the same manner as in Synthesis of Intermediate D6-5 in Synthesis Example 1, except that Intermediate D81-4 was used instead of Intermediate D6-4.
Intermediate D81-6 was obtained in substantially the same manner as in Synthesis of Intermediate D6-6 in Synthesis Example 1, except that Intermediate D81-5 was used instead of Intermediate D6-5.
Intermediate D81-7 was obtained in substantially the same manner as in Synthesis of Intermediate D6-7 in Synthesis Example 1, except that Intermediate D81-6 was used instead of Intermediate D6-6.
5.22 g (3.95 mmol) of Compound D81 was obtained in substantially the same manner as in Synthesis of Compound D6 in Synthesis Example 1, except that Intermediate D81-7 was used instead of Intermediate D6-7.
Intermediate D302-1 was synthesized in substantially the same manner as in Synthesis of Intermediate D6-1 in Synthesis Example 1, except that acetone-d6 was used instead of 2-adamantanone.
Intermediate D302-2 was obtained in substantially the same manner as in Synthesis of Intermediate D6-2 in Synthesis Example 1, except that Intermediate D302-1 was used instead of Intermediate D6-1.
Intermediate D302-3 was obtained in substantially the same manner as in Synthesis of Intermediate D6-3 in Synthesis Example 1, except that Intermediate D302-2 was used instead of Intermediate D6-2.
Intermediate D302-4 was obtained in substantially the same manner as in Synthesis of Intermediate D6-4 in Synthesis Example 1, except that Intermediate D302-3 was used instead of Intermediate D6-3.
Intermediate D302-5 was obtained in substantially the same manner as in Synthesis of Intermediate D6-5 in Synthesis Example 1, except that Intermediate D302-4 was used instead of Intermediate D6-4.
Intermediate D302-6 was obtained in substantially the same manner as in Synthesis of Intermediate D6-6 in Synthesis Example 1, except that Intermediate D302-5 was used instead of Intermediate D6-5.
Intermediate D302-7 was obtained in substantially the same manner as in Synthesis of Intermediate D6-7 in Synthesis Example 1, except that Intermediate D302-6 was used instead of Intermediate D6-6.
5.73 g (5.69 mmol) of Compound D302 was obtained in substantially the same manner as in Synthesis of Compound D6 in Synthesis Example 1, except that Intermediate D302-7 was used instead of Intermediate D6-7.
Compounds synthesized in the Synthesis Examples 1 to 5 were identified by 1H nuclear magnetic resonance (NMR) and matrix-assisted laser desorption/ionization mass spectrometry time-of-flight mass spectroscopy (MALDI-TOF MS). The results thereof are shown in Table 1. Methods of synthesizing compounds other than the compounds synthesized in Synthesis Examples 1 to 5 may be easily understood by those skilled in the art by referring to the synthesis pathways and raw materials described above.
1H NMR (CDCl3, 500 MHz)
4JH-H = 0.8 Hz), 7.44-7.40 (m, 4H), 7.36-7.20 (m, 10H),
HOMO and LUMO energy levels of Compounds D6, D12, D27, D81, and D302 were evaluated according to the method in Table 2. The results thereof are shown in Table 3.
Film 1 having a thickness of 40 nm was prepared by vacuum-co-depositing ETH66, HTH29, and D6 on a quartz substrate at a vacuum degree of 10−7 torr. Here, regarding the amounts of Compounds ETH66, HTH29, and D6, a weight ratio of Compound ETH66 to Compound HTH29 was 3:7, and the content of Compound D6 was 10 parts by weight based on 100 parts by weight of the film. Subsequently, Films 2 to 5 were respectively prepared in substantially the same manner as in synthesis of Film 1, except that Compounds D12, D27, D81, or D302 was respectively used instead of Compound D6.
The emission spectrum of each of the Films was measured by using a Hamamatsu Quantaurus-QY absolute PL quantum yield measurement system equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and utilizing PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). At the time of measurement, the excitation wavelength was measured by scanning from 320 nm to 380 nm at 10 nm intervals, of which the spectrum measured at the excitation wavelength of 340 nm was taken, and the maximum emission wavelength of the dopant included in each Film was obtained. The results are shown in Table 4.
Subsequently, regarding the emission quantum yield, the excitation wavelengths of Films 1 to 5 were measured by using Quantaurus-QY Absolute PL spectrometer (Hamamatsu) by scanning from 320 nm to 380 nm at 10 nm intervals, of which the spectrum at the excitation wavelength of 340 nm was taken to obtain the emission quantum yield (PLQY). Emission quantum yield of the dopant include in each Film is shown in Table 4.
Referring to the results of Table 4, Compounds D6, D12, D27, D81, and D302 were found to emit blue light having excellent PLQY.
The PL spectrum of each of Films 1 to 5 was evaluated at room temperature by using a time-resolved photoluminescence (TRPL) measurement system, FluoTime 300 (available from PicoQuant), and a pumping source, PLS 340 (available from PicoQuant, excitation wavelength=340 nm, spectral width=20 nm). Then, a wavelength of the main peak in the PL spectrum was determined, and upon photon pulses (pulse width=500 picoseconds, ps) applied to the film by PLS 340, the number of photons emitted at the wavelength of the main peak for each film was repeatedly measured overtime by time-correlated single photon counting (TCSPC), thereby obtaining TRPL curves available for the sufficient fitting. Based on the results obtained therefrom, one or more exponential decay functions were set forth for the fitting, thereby obtaining Tdecay(Ex), i.e., a decay time, for each of Films 1 to 5. The results thereof are shown in Table 5. The functions used for the fitting are as described in Equation 20, and a decay time Tdecay having the largest value among values for each of the exponential decay functions used for the fitting was taken as Tdecay(Ex), i.e., a decay time. Here, during the same measurement time as the measurement time for obtaining TRPL curves, the same measurement was repeated once more in a dark state (i.e., a state where a pumping signal incident on each of the films was blocked), thereby obtaining a baseline or a background signal curve available as a baseline for the fitting:
Referring to the results of Table 5, Compounds D6, D12, D27, D81, and D302 were found to have excellent decay time.
As an anode, a 15 Ohms per square centimeter (Ω/cm2) (1,200 Å) ITO glass substrate (available from Corning Inc.) was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes in each solvent, cleaned with ultraviolet rays for 30 minutes, and then with ozone, and was mounted on a vacuum deposition apparatus.
2-TNATA was vacuum-deposited on the anode 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 D6 (as the first compound), Compound ETH66 (as the second compound), and Compound HTH29 (as the third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 400 Å. Here, the content of Compound D6 was 10 wt %, based on 100 wt % of the total weight of the emission layer, and the weight ratio of Compound ETH66 to Compound HTH29 was 3:7.
Compound ETH2 was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq3 was 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 on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing the manufacture of an organic light-emitting device.
Organic light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 6 were used instead of the first compound, the second compound, and the third compound in the formation of each respective emission layer.
The driving voltage (V), color purity (CIEx,y), luminescence efficiency (cd/A), color-conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95) at 1,000 cd/m2 of the organic light-emitting devices manufactured in Examples 1 to 6 were measured by using Keithley source-measure unit (SMU) 236 and a luminance meter PR650. The results thereof are shown in Tables 6 and 7. In Table 7, the lifespan (T95) indicates a time (in hours) that it took for the luminance of each light-emitting device to decline to 95% of its initial luminance. The electroluminescence spectra, the luminance-luminescence efficiency graph, and the time-luminance graph of Examples 1 to 6 are respectively shown in
Referring to the results of Tables 6 and 7, the organic light-emitting devices of Examples 1 to 6 were each found to have excellent driving voltage, color purity, luminescence efficiency, color-conversion efficiency, and lifespan characteristics, and to emit dark blue light.
An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound D6 (as the first compound), Compound ETH66 (as the second compound), Compound HTH29 (as the third compound), and Compound DFD1 (as the fourth compound) were vacuum-deposited on the hole transport layer instead of Compound D6 (as the first compound), Compound ETH66 (as the second compound), and Compound HTH29 (as the third compound) in the formation of the emission layer. Here, the content of Compound D6 was 10 wt %, based on 100 wt % of the total weight of the emission layer, the content of Compound DFD1 was 0.5 wt %, based on 100 wt % of the total weight of the emission layer, and the weight ratio of Compound ETH66 to Compound HTH29 was 3:7.
An organic light-emitting device was manufactured in substantially the same manner as in Example 7, except that Compound DFD2 was used instead of Compound DFD1 as the fourth compound.
The driving voltage (V), color purity (CIEx,y), luminescence efficiency (cd/A), color-conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95) at 1,000 cd/m2 of the organic light-emitting devices manufactured in Examples 7 and 8 were measured by using the same methods as those in Evaluation Example 4. The results thereof are shown in Tables 8 and 9. The electroluminescence spectra, the luminance-luminescence efficiency graph, and the time-luminance graph of Examples 7 and 8 are respectively shown in
Referring to the results of Tables 8 and 9, the organic light-emitting devices of Examples 7 and 8 were each found to have excellent driving voltage, color purity, luminescence efficiency, color-conversion efficiency, and lifespan characteristics, and to emit dark blue light.
An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound D6 (as the first compound) and Compound HTH29 (as the third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 300 Å, instead of Compound D6 (as the first compound), Compound ETH29 (as the second compound), and Compound HTH66 (as the third compound) that were used to form an emission layer having a thickness of 400 Å. Here, the content of Compound D6 was 10 wt %, based on 100 wt % of the total weight of the emission layer.
An organic light-emitting device was manufactured in substantially the same manner as in Example 11, except that Compound CE1 was used instead of Compound D6 to form an emission layer.
The driving voltage (V), color purity (CIEx,y), luminescence efficiency (cd/A), color-conversion efficiency (cd/A/y), maximum emission wavelength (nm), and lifespan (T95 at room temperature) at 1,000 cd/m2 of the organic light-emitting devices manufactured in Example 11 and Comparative Example 1 were measured by using the same methods as those in Evaluation Example 4. The results thereof are shown in Tables 10 and 11. The electroluminescence spectra, the luminance-luminescence efficiency graph, and the time-luminance graph of Example 11 and Comparative Example 1 are respectively shown in
Referring to the results of Tables 10 and 11, the organic light-emitting device of Example 11 was found to have excellent driving voltage, color purity, luminescence efficiency, color-conversion efficiency, and lifespan characteristics, and to emit dark blue light, as compared with Comparative Example 1.
As apparent from the foregoing description, the light-emitting device may have excellent driving voltage, current density, high luminescence efficiency, and long lifespan, and may be used in the manufacture of a high quality electronic apparatus.
As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
In addition, the terms “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.
Also, any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
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 figures, 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 their equivalents.
| Number | Date | Country | Kind |
|---|---|---|---|
| 10-2020-0086448 | Jul 2020 | KR | national |
