Light emitting device and electronic device including the same
By introducing a sandwich structure of specific compounds into the light-emitting device, the problems of insufficient luminous efficiency and lifetime were solved, achieving high efficiency and long lifetime luminous performance.
Patent Information
- Application Number
- CN202110765755.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-07-13
- Filing Date
- 2021-07-07
- Publication Date
- 2026-01-02
- Estimated Expiration
- 2041-07-07
AI Technical Summary
Existing light-emitting devices are insufficient in terms of luminous efficiency and lifespan, making it difficult to meet high-performance requirements.
A sandwich structure is adopted, comprising a first compound represented by Formula 1 and a second compound containing nitrogen-containing C1-C60 cyclic groups, combined with a third compound and a fourth compound, to improve luminescence efficiency and delayed fluorescence performance.
This improved the luminous efficiency and extended the lifespan of the light-emitting device, meeting the demand for high-performance light emission.
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Figure CN113937229B_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0086448, filed on July 13, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more aspects of embodiments of this disclosure relate to light-emitting devices and electronic devices including light-emitting devices. Background Technology
[0004] The light-emitting device is a self-emitting device, which has excellent characteristics in terms of wide viewing angle, high contrast, short response time, brightness, driving voltage and / or response speed.
[0005] The light-emitting device may include a first electrode on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied from the first electrode can move through the hole transport region to the emitter layer, and electrons supplied from the second electrode can move through the electron transport region to the emitter layer. Charge carriers such as holes and electrons recombine in the emitter layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the Invention
[0006] One or more aspects of embodiments of this disclosure relate to light-emitting devices having high luminous efficiency and long lifespan, as well as electronic devices including light-emitting devices.
[0007] Other aspects will be set forth in part in the description which follows, and in part will be obvious from the description or may be recognized by practice of the embodiments of this disclosure presented.
[0008] According to one or more embodiments, the light-emitting device may include:
[0009] First electrode;
[0010] The second electrode facing the first electrode; and
[0011] A sandwich layer is located between the first electrode and the second electrode, the sandwich layer including an emission layer.
[0012] The interlayer may include:
[0013] i) the first compound represented by formula 1; and
[0014] ii) Including nitrogen-containing C1-C atoms lacking at least one π electron. 60 A second compound with a cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
[0015] The first compound, the second compound, the third compound, and the fourth compound can be different from each other:
[0016] Formula 1
[0017]
[0018] Formula 3
[0019]
[0020] wherein, in Formula 1, M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
[0021] In Formula 1, X1to X4may each independently be C or N,
[0022] In Formula 1, i) the bond between X1and M can be a coordinate bond, and ii) one of the bonds between X2and M, between X3and M, and between X4and M can be a coordinate bond, and the other two bonds can each be a covalent bond,
[0023] In Formula 1, ring CY1may be i) a five-membered ring containing X1, ii) a five-membered ring containing X1fused with at least one six-membered ring, or iii) a six-membered ring containing X1,
[0024] In Formula 1, ring CY2may be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0025] In Formula 1, X 31 to X 36 and X 41 to X 44 may each independently be C or N,
[0026] In Formula 1, X 51 may be *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-Ge(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R 5a )=C(R 5b)-*', *-C(=S)-*', or *-C≡C-*', and * and *' can each indicate a binding site with a neighboring atom.
[0027] In Equation 1, L1 can be a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,
[0028] In Equation 1, b1 can be an integer selected from 1 to 5.
[0029] In Equation 1, R1 to R5, R 5a and R 5b Each can be independently a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Arylthio, -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),
[0030]
[0031] In Equation 1, c1 can be an integer selected from 0 to 5, a1 and a4 can each be an integer selected from 0 to 4 independently, a2 can be an integer selected from 0 to 10, and a3 can be an integer selected from 0 to 6, provided that the sum of a1 to a4 can be 1 or greater, and the number is a1 *-(L1).b1 -(R1) c1 at least one of R2 in an amount of a2, at least one of R3 in an amount of a3, at least one of R4 in an amount of a4, or any combination thereof, can each independently be a group represented by Formula 1-1 or a group represented by Formula 1-2,
[0032] In Formula 1-1 and Formula 1-2, L7may be a single bond, an unsubstituted or substituted C3-C 10a cycloalkyl group, or an unsubstituted or substituted C1-C 60 heterocyclyl group, 10a heterocyclyl group, 60 heterocyclyl group,
[0033] In Formula 1-1 and Formula 1-2, b7may be an integer selected from 1 to 5,
[0034] In Formula 1-1 and Formula 1-2, ring CY7may be a C3-C 60 cycloalkyl group, or a C1-C 60 heterocyclyl group,
[0035] In Formula 1-1 and Formula 1-2, n7may be an integer selected from 1 to 5,
[0036] In Formula 1-1, ring CY8may be a non-aromatic C3-C 60 cycloalkyl group, or a non-aromatic C1-C 60 heterocyclyl group,
[0037] In Formula 1-1 and Formula 1-2, R7to R9may each be understood by reference to the description of R1provided herein,
[0038] In Formula 1-1 and Formula 1-2, a7and a8may each independently be an integer selected from 0 to 20,
[0039] In Formula 3, ring CY 71 and ring CY 72 may each independently be a π-electron rich C3-C 60 cycloalkyl group, or a pyridyl group,
[0040] In Formula 3, X 71 may be a single bond or a linking group comprising O, S, N, B, C, Si, or any combination thereof,
[0041] In Formula 3, * indicates a binding site to an adjacent atom,
[0042] at least two of the groups represented by *-(L1) b1 -(R1) c1 may optionally be bound to form an unsubstituted or substituted C3-C10a substituted C3-C 60 a carbocyclic group, or a heterocyclic group, which is unsubstituted or substituted by at least one R 10a substituted C1-C 60 a heterocyclic group, which is unsubstituted or substituted by at least one R
[0043] at least two of the R2in the number a2may optionally be combined to form an unsubstituted or substituted C3-C 10a substituted C3-C 60 a carbocyclic group, or a heterocyclic group, which is unsubstituted or substituted by at least one R 10a substituted C1-C 60 a heterocyclic group, which is unsubstituted or substituted by at least one R
[0044] at least two of the R3in the number a3may optionally be combined to form an unsubstituted or substituted C3-C 10a substituted C3-C 60 a carbocyclic group, or a heterocyclic group, which is unsubstituted or substituted by at least one R 10a substituted C1-C 60 a heterocyclic group, which is unsubstituted or substituted by at least one R
[0045] at least two of the R4in the number a4may optionally be combined to form an unsubstituted or substituted C3-C 10a substituted C3-C 60 a carbocyclic group, or a heterocyclic group, which is unsubstituted or substituted by at least one R 10a substituted C1-C 60 a heterocyclic group, which is unsubstituted or substituted by at least one R
[0046] at least two of R1to R5, R 5a and R 5b may optionally be combined to form an unsubstituted or substituted C3-C 10a substituted C3-C 60 a carbocyclic group, or a heterocyclic group, which is unsubstituted or substituted by at least one R 10a substituted C1-C 60 a heterocyclic group, which is unsubstituted or substituted by at least one R
[0047] R 10a may be:
[0048] deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0049] each independently C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof;
[0050] each independently C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, or C6-C 60 arylthio: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ) or any combination thereof; or
[0051] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q31 )(Q 32 ),
[0052] wherein Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 alkyl substituted with deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; or C3-C 60 carbocyclic group or C1-C 60 heterocyclic group: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, or any combination thereof, and
[0053] The following compounds can be excluded from the third compound:
[0054]
[0055] According to one or more embodiments, an electronic device can include a light emitting device.
[0056] According to one or more embodiments, an organometallic compound can be represented by Formula 1. BRIEF DESCRIPTION OF DRAWINGS
[0057] The above and other aspects, features, and advantages of certain embodiments of the present disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0058] Figure 1 is a schematic cross-sectional view of a light emitting device according to one or more embodiments;
[0059] Figure 2 is a schematic cross-sectional view of an electronic device according to one or more embodiments;
[0060] Figure 3 is a schematic cross-sectional view of an electronic device according to one or more embodiments;
[0061] Figure 4 is a graph showing electroluminescence (EL) spectra of the organic light emitting devices of Examples 1 to 6 and 11 and Comparative Example 1;
[0062] Figure 5 is a graph of wavelength (nanometer, nm) versus normalized intensity (arbitrary unit, a.u.) showing EL spectra of the organic light emitting devices of Examples 1, 7 and 8;
[0063] Figure 6 is a graph of luminance (cd / m 2 ) versus luminous efficiency (cd / A) of the organic light emitting devices of Examples 1 to 8 and 11 and Comparative Example 1; and
[0064] Figure 7 is a graph of time (hour) versus luminance (percent, %) of the organic light emitting devices of Examples 1 to 8 and 11 and Comparative Example 1. DETAILED DESCRIPTION
[0065] Reference will now be made in detail to the 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 can have different forms and should not be construed as being limited to the description set forth herein. Accordingly, the embodiments are merely described below, by referring to the drawings, to explain aspects of the present description. The term “and / or” as used herein comprises any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b and c” can indicate 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.
[0066] The expressions such as “at least selected from”, “one of”, and “selected from”, when preceded by a list of elements, modify the entire list of elements and not the individual elements of the list. Further, the use of “may” when describing embodiments of the disclosure indicates “one or more implementations of the disclosure”.
[0067] The light emitting device can include: a first electrode; a second electrode facing the first electrode; a sandwich layer between the first electrode and the second electrode and including an emission layer, wherein the sandwich layer can include:
[0068] i) a first compound represented by Formula 1; and
[0069] ii) a second compound including at least one π-electron deficient nitrogen-containing C1-C 60 cyclic group, a third compound including a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
[0070] The first compound, the second compound, the third compound, and the fourth compound can be different from each other:
[0071] Formula 1
[0072]
[0073] wherein Formula 1 can be understood by reference to the description of Formula 1 provided herein.
[0074] Formula 3
[0075]
[0076] wherein, in Formula 3, ring CY 71 and ring CY 72 may each independently be a π-electron rich C3-C 60 cyclic group or a pyridyl group,
[0077] In Formula 3, X 71 may be a single bond or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and
[0078] In Formula 3, * indicates a binding site to an adjacent atom.
[0079] The following compounds can be excluded from the third compound:
[0080]
[0081] Description of the first compound to the fourth compound
[0082] The second compound can include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0083] In some embodiments, the light emitting device can further include at least one of a second compound and a third compound, in addition to the first compound.
[0084] In some embodiments, the light emitting device can further include a fourth compound, in addition to the first compound.
[0085] In some embodiments, the light emitting device can include the first compound, the second compound, the third compound, and the fourth compound.
[0086] In some embodiments, the interlayer can include the second compound. The interlayer can further include a third compound, a fourth compound, or any combination thereof, in addition to the first compound and the second compound.
[0087] In some embodiments, the difference (in 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 can be about 0 eV or more and about 0.5 eV or less (or, about 0 eV or more and about 0.3 eV or less).
[0088] In some embodiments, the fourth compound can be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0089] In some embodiments, the fourth compound can be a compound including C8-C 60 a polycyclic group including at least two cyclic groups that are fused to each other and share a boron atom (B).
[0090] In some embodiments, the fourth compound can include a fused ring, where at least one third ring can be fused to at least one fourth ring,
[0091] The third ring can 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 norbornane group, a bicyclo[l.l.l]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a phenyl group, a pyridyl group, a pyrimidyl group, a pyridazyl group, a pyrazyl group, or a triazyl group, and
[0092] The fourth ring can 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.
[0093] In one or more embodiments, the interlayer can include the fourth compound. In addition to the first compound and the fourth compound, the interlayer can include the second compound, the third compound, or any combination thereof.
[0094] In one or more embodiments, the interlayer can include the third compound. In some embodiments, the third compound can not include a compound represented by Formula 3-1.
[0095] The emissive layer in the interlayer can include: i) the first compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof.
[0096] The emissive layer can emit phosphorescence or fluorescence emitted by the first compound. In some embodiments, the phosphorescence or fluorescence emitted by the first compound can be blue light.
[0097] In some embodiments, the emissive layer in the light-emitting device can include a first compound and a second compound, and the first compound and the second compound can form an exciplex.
[0098] In some embodiments, the emissive layer in the light-emitting device can include a first compound, a second compound, and a third compound, and the first compound and the second compound can form an exciplex.
[0099] In some embodiments, the emissive layer in the light-emitting device can include a first compound and a fourth compound, and the fourth compound can be used to improve color purity, light-emitting efficiency, and / or lifetime characteristics of the light-emitting device.
[0100] In some embodiments, the second compound can include a compound represented by Formula 2:
[0101] Formula 2
[0102]
[0103] wherein, in Formula 2,
[0104] L 51 to L 53 may each independently be a single bond, an unsubstituted or substituted C3-C 10a cycloalkyl group, or an unsubstituted or substituted C1-C 60 heterocyclyl group, 10a 60
[0105] b51 to b53 can each independently be an integer selected from 1 to 5,
[0106] X 54 may be N or C(R 54 ), X 55 may be N or C(R 55 ), X 56 may be N or C(R 56 ), and at least one selected from X 54 to X 56 may be N,
[0107] R 51 to R 56 may each be understood by referring to the description of R 51 to R 56 provided herein, and
[0108] R 10a may be understood by referring to the description of R 10a provided herein.
[0109] In one or more embodiments, the third compound can 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:
[0110] Formula 3-1
[0111]
[0112] Formula 3-2
[0113]
[0114] Formula 3-3
[0115]
[0116] Formula 3-4
[0117]
[0118] Formula 3-5
[0119]
[0120] wherein, in Formula 3-1 to Formula 3-5,
[0121] Ring CY 71 to Ring CY 74 may each independently be a π-electron rich C3-C 60 cyclic group or pyridyl group,
[0122] X 82 may be a single bond, O, S, N-[(L 82 ) b82 -R 82 ], C(R 82a )(R 82b ) or Si(R 82a )(R 82b ),
[0123] X 83 may be a single bond, O, S, N-[(L 83 ) b83 -R 83 ], C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0124] X 84 may be O, S, N-[(L 84 ) b84 -R 84], C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0125] X 85 may be C or Si,
[0126] L 81 to L 85 may each independently be a single bond, *-C(Q4)(Q5)-*, 10a a π -electron rich C3-C 60 cyclic group, or an unsubstituted or at least one R 10a substituted pyridyl group, wherein Q4and Q5may each be understood by reference to the description of Q1provided herein,
[0127] b81 to b85 may each independently be an integer selected from 1 to 5,
[0128] R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may each be understood by reference to the description of R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b provided herein,
[0129] a71 to a74 may each independently be an integer selected from 0 to 20, and
[0130] R 10a may be understood by reference to the description of R 10a provided herein.
[0131] In some embodiments, the fourth compound can be a compound represented by formula 502, a compound represented by formula 503, or any combination thereof:
[0132] Formula 502
[0133]
[0134] Formula 503
[0135]
[0136] wherein, in Formula 502 and Formula 503,
[0137] Ring A 501 to Ring A 504 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0138] Y 505 may be O, S, N(R 505 ), B(R 505 ), C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0139] Y 506 may be O, S, N(R 506 ), B(R 506 ), C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0140] Y 507 may be O, S, N(R 507 ), B(R 507 ), C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0141] Y 508 may be O, S, N(R 508 ), B(R 508 ), C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0142] Y 51 and Y 52 may each independently be B, P(=O) or S(=O),
[0143] R 500a , R 500b , R 501 to R 508 , R 505a , R 505b , R506a 506b 507a 507b 508a 508b 500a 500b 501 508 505a 505b 506a 506b 507a 507b 508a 508b
[0144] a501 to a504 can each independently be an integer selected from 0 to 20, and
[0145] 10a 10a
[0146] Description of Formula
[0147] In Formula 1, M can be platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu).
[0148] In Formula 1, X1 to X4 can each independently be C or N.
[0149] In some embodiments, in Formula 1, X1 can be C, and C can be a carbon atom in a carbene moiety.
[0150] In one or more embodiments, in Formula 1, X1 can be N.
[0151] In one or more embodiments, in Formula 1, X2 and X3 can each be C, and X4 can be N.
[0152] In Formula 1, i) the bond between X1 and M can be a coordinate bond, and ii) one of the bonds between X2 and M, between X3 and M, and between X4 and M can be a coordinate bond, and the other two bonds can each be a covalent bond.
[0153] In some embodiments, in Formula 1, the bond between X2 and M and the bond between X3 and M can each be a covalent bond, and the bond between X4 and M can be a coordinate bond.
[0154] In Formula 1, ring CY1may be i) a five-membered ring containing X1, ii) a five-membered ring containing X1fused with at least one six-membered ring, or iii) a six-membered ring containing X1. In some embodiments, in Formula 1, ring CY1may be i) a five-membered ring containing X1or ii) a five-membered ring containing X1fused with at least one six-membered ring. For example, ring CY1may include a five-membered ring bound to M in Formula 1 via X1.
[0155] In some embodiments, the five-membered ring containing X1in ring CY1in Formula 1may be a pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, or thiadiazolyl.
[0156] In some embodiments, the six-membered ring that can be fused with the five-membered ring containing X1in ring CY1in Formula 1or the six-membered ring containing X1may be a phenyl, pyridyl, or pyrimidyl.
[0157] In some embodiments, in Formula 1, the group represented by may be represented by one of Formula CY1-1 to Formula CY1-42:
[0158]
[0159]
[0160] wherein, in Formula CY1-1 to Formula CY1-42,
[0161] Y1may be O, S, N, C, or Si,
[0162] * indicates a binding site to M in Formula 1, and
[0163] * indicates a binding site to an adjacent atom in Formula 1.
[0164] In some embodiments, in Formula CY1-1 to Formula CY1-8, X1may be C, and X1in Formula CY1-9 to Formula CY1-42 may be N.
[0165] In Formula 1, ring CY2may be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group.
[0166] In some embodiments, ring CY2may be a phenyl, pyridyl, pyrimidyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzosilolyl.
[0167] In some embodiments, in Formula 1, the group represented by may be a group represented by one of Formula CY2-1 to Formula CY2-11:
[0168]
[0169] Among them, in equations CY2-1 to CY2-11,
[0170] Y2 can be O, S, N, C, or Si.
[0171] *Indicates the binding site with M in Formula 1.
[0172] *' indicates the binding site with loop CY1 in Formula 1, and
[0173] *"Indicates X in Equation 1 51 The binding site.
[0174] In Equation 1, X 31 To X 36 and X 41 To X 44 Each can be either C or N independently.
[0175] In some implementations, in Equation 1, X 31 To X 36 and X 41 To X 44 Each can be C.
[0176] In Equation 1, X 51 It can be *-N(R5)-*', *-B(R5)-*', *-P(R5)-*', *-C(R5)-*', or *-C(R5)-*'. 5a (R) 5b )-*'、*-Si(R 5a (R) 5b )-*'、*-Ge(R 5a (R) 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R 5a )=C(R 5b R5, R', *-C(=S)-*', or *-C≡C-*'. * and *' each indicate the binding site with a neighboring atom. 5a and R 5b You can refer to the descriptions of R5 and R provided in this article. 5a and R 5b To understand this, use the description. R 5a and R 5b They may optionally combine with each other to form unsubstituted or by at least one R 10a Replacement C3-C 60Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups (e.g., compound 109, etc.).
[0177] In some implementations, in Equation 1, X 51 It can be *-N(R5)-*', *-B(R5)-*', or *-C(R5)-*'. 5a (R) 5b )-*'、*-Si(R 5a (R) 5b )-*', *-S-*' or *-O-*'.
[0178] In Equation 1, L1 can be a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups.
[0179] In Equation 1, b1 indicates the number of L1s, and b1 can be an integer selected from 1 to 5. When b1 is 2 or greater, at least two L1s can be the same or different from each other. In some implementations, b1 can be 1 or 2.
[0180] In Equation 1, R1 to R5, R 5a and R 5b Each can be independently a group represented by Formula 1-1, a group represented by Formula 1-2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60thioaryl, -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):
[0181]
[0182] Formula 1-1 and Formula 1-2 can each be understood by reference to the description provided herein for Formula 1-1 and Formula 1-2.
[0183] In Formula 1, c1 can be an integer selected from 0 to 5, a1 and a4 can each independently be an integer selected from 0 to 4, a2 can be an integer selected from 0 to 10, and a3 can be an integer selected from 0 to 6, provided that the sum of a1 to a4 can be 1 or greater, and the at least one of *-(L1) b1 -(R1) c1 The at least one of the at least one of *-(L1)
[0184] In some embodiments, in Formula 1, a4 can be an integer selected from 1 to 4, and the at least one of the at least one of R4 can each independently be a group represented by Formula 1-1 or a group represented by Formula 1-2.
[0185] L7in Formula 1-1 and Formula 1-2 can be a single bond, an unsubstituted or substituted C3-C 10a carbon ring group, or an unsubstituted or substituted C1-C 60 heterocyclic ring group. 10a heterocyclic ring group. 60 heterocyclic ring group.
[0186] In Formula 1-1 and Formula 1-2, b7 indicates the number of L7, and b7 can be an integer selected from 1 to 5. When b7 is 2 or greater, at least two L7can be the same as or different from each other. In some embodiments, b7 can be 1 or 2.
[0187] In Formula 1-1 and Formula 1-2, ring CY7may be a C3-C 60 heterocyclic ring group. 60 heterocyclic ring group.
[0188] In some embodiments, in Formula 1-1 and Formula 1-2, ring CY7may be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring and at least one second ring are fused,
[0189] The first ring can be a cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl, or phenyl group, and
[0190] The second ring can be a pyrrolyl, furanyl, thienyl, silolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, 1,2-azaborinanyl, 1,3-azaborinanyl, 1,4-azaborinanyl, 1,2-dihydro-1,2-azaborinanyl, 1,4-oxaborinanyl, 1,4-thiaborinanyl, or 1,4-dihydroborinanyl group.
[0191] In one or more embodiments, in Formula 1-1 and Formula 1-2, ring CY7may be a phenyl, naphthyl, phenanthryl, carbazolyl, [1,2]azaborinano[1,2-a][1,2]azaborinanyl, or benzo[1,2]azaborinano[1,2-a][1,2]azaborinanyl group.
[0192] In one or more embodiments, in Formula 1-1 and Formula 1-2, ring CY7may be a group represented by one of Formula CY7-1 to Formula CY7-33:
[0193]
[0194]
[0195] In Formula CY7-1 to Formula CY7-33, * indicates a binding site with L7in Formula 1-1 and Formula 1-2.
[0196] In Formula 1-1 and Formula 1-2, n7indicates the number of groups represented by and n7may be an integer selected from 1 to 5. When n7is 2 or more, at least two of the groups represented by may be the same as or different from each other. In some embodiments, n7may be 1.
[0197] In Formula 1-1, ring CY8may be a non-aromatic C3-C 60Carbocyclic groups or non-aromatic C1-C 60 Heterocyclic groups.
[0198] In some embodiments, in Formula 1-1, cycloCY8 may be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, or bicyclo[2.2.2]octyl.
[0199] In one or more embodiments, in Formula 1-1, cyclo CY8 may be a group represented by one of Formulas CY8-1 to CY8-8:
[0200]
[0201] In formulas CY8-1 to CY8-8, * indicates the binding site with a neighboring atom in formula 1, and *' indicates the binding site with L7 in formula 1-1.
[0202] In Equations 1-1 and 1-2, R7 to R9 can each be understood by referring to the description of R1 provided herein.
[0203] In Equations 1-1 and 1-2, a7 and a8 may indicate the quantities of R7 and R8, respectively, and a7 and a8 may each be an integer selected independently from 0 to 20. When a7 is 2 or greater, at least two R7s may be the same or different from each other. When a8 is 2 or greater, at least two R8s may be the same or different from each other.
[0204] In Equation 1, i) the number of a1 is determined by *-(L1). b1 -(R1) c1 At least two of the indicated groups may optionally be linked to each other (via single bond, double bond, or first linking group) to form an unsubstituted or R-shaped group. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 (ii) At least two of the number a2 of the heterocyclic groups R2 may optionally be linked together (via a single bond, double bond or first linking group) to form an unsubstituted or at least one R 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 (iii) At least two of the three heterocyclic groups (a3) may optionally be linked together (via a single bond, double bond, or first linking group) to form an unsubstituted or substituted heterocyclic group. 10aReplacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 (iv) At least two of the R4 groups in the number of a4 may optionally be linked to each other (via a single bond, double bond or first linking group) to form an unsubstituted or at least one R4 group. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, and / or v) R1 to R5, R 5a and R 5b At least two of them may optionally be linked to each other (via single bond, double bond or first linking group) to form an unsubstituted or R-type compound. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic group. The first linking group may be selected from *-N(R) 95 )-*'、*-B(R 95 )-*'、*-P(R 95 )-*'、*-C(R 95a (R) 95b )-*'、*-Si(R 95a (R) 95b )-*'、*-Ge(R 95a (R) 95b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 95 )=*'、*=C(R 95 )-*'、*-C(R 95a )=C(R 95b )-*', *-C(=S)-*' and *-C≡C-*', and R 95 R 95a and R 95b Each can refer to the R provided in this article. 10a To understand this, we need to refer to the description.
[0205] In some embodiments, the first compound represented by Formula 1 may include at least one deuterium.
[0206] 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.
[0207] In one or more embodiments, in Formula 1, 1) a1 can not be 0, and 2) at least one of the *-(L1) b1 -(R1) c1 groups in Formula 1 can include at least one deuterium. b1 -(R1) c1 In one or more embodiments, in Formula 1, the group represented by *-(L1) 10a -(R1) 60 may include at least one deuterium. 10a -(R1) 60 may include at least one deuterium.
[0208] In one or more embodiments, in Formula 1, the group represented by b1 -(R1) c1 may include at least one deuterium.
[0209] In one or more embodiments, in Formula 1, the group represented by may be represented by one of Formula CY1(1) to Formula CY1(6):
[0210]
[0211] In Formula CY1(1) to Formula CY1(6),
[0212] X1may be selected from O, S, N(R 21 ), C(R 21 )(R 22 ), and Si(R 21 )(R 22 ),
[0213] L 11 and c11may be understood by reference to the description of L1and c1provided herein, respectively,
[0214] R 11 to R 13 may each be understood by reference to the description of R1provided herein, where R 11 to R 13 may each not be hydrogen,
[0215] * indicates a site of attachment to M in Formula 1, and
[0216] *’ indicates a site of attachment to an adjacent atom in Formula 1.
[0217] In some embodiments, in Formula CY1(1) to Formula CY1(5), 1) L 11 may not be a single bond, and 2) at least one of the R11 at least one R 10a substituted C3-C 60 carbon ring group or unsubstituted or substituted C1-C 10a substituted C1-C 60 heterocyclic ring group.
[0218] In some embodiments, X1may be C in Formula CY1(1) to Formula CY1(4) and N in Formula CY1(5) and Formula CY1(6).
[0219] In some embodiments, L 11 may be unsubstituted or substituted with at least one R 10a substituted C5-C 30 carbon ring group or unsubstituted or substituted C1-C 10a substituted C1-C 30 heterocyclic ring group.
[0220] In one or more embodiments, the group represented by in Formula 1 can be one of the groups represented by Formula CY2(1) to Formula CY2(26):
[0221]
[0222]
[0223] wherein, in Formula CY2(1) to Formula CY2(26),
[0224] X2may be understood by reference to the description provided herein for X 21 ,
[0225] X 21 may be selected from O, S, N(R 21 ), C(R 21 )(R 22 ), and Si(R 21 )(R 22 ),
[0226] R 21 to R 23 may each be understood by reference to the description provided herein for R2, where R 21 to R 23 may each not be hydrogen,
[0227] * indicates the site of bonding to M in Formula 1, and
[0228] * indicates the site of bonding to ring CY1in Formula 1, and
[0229] * indicates a binding site to X in Formula 1, 51
[0230] In one or more embodiments, in Formula 1, the group represented by may be a group represented by one of Formula CY3(1) to Formula CY3(7):
[0231]
[0232] wherein, in Formula CY3(1) to Formula CY3(7),
[0233] X3may be understood by reference to the description of X3provided herein,
[0234] R 31 , R 36 may each be understood by reference to the description of R3provided herein, wherein R 31 , R 36 may each not be hydrogen,
[0235] * indicates a binding site to M in Formula 1,
[0236] * indicates a binding site to an adjacent atom in Formula 1, and
[0237] * indicates a binding site to X in Formula 1, 51
[0238] In one or more embodiments, in Formula 1, the group represented by may be a group represented by one of Formula CY4(1) to Formula CY4(8):
[0239]
[0240] wherein, in Formula CY4(1) to Formula CY4(8),
[0241] X4may be understood by reference to the description of X4provided herein,
[0242] T4may be a group represented by Formula 1-1 or a group represented by Formula 1-2,
[0243] R 41 , R 43 , and R 44 may each be understood by reference to the description of R4provided herein, wherein R 41 , R 43 , and R 44 may each not be hydrogen,
[0244] * indicates a binding site to M in Formula 1, and
[0245] indicates a binding site to the adjacent atom in Formula 1.
[0246] In Formula 2, b51 to b53 can respectively indicate the number of L 51 to L 53 , and b51 to b53 can each be an integer selected from 1 to 5. When b51 is 2 or more, at least two L 51 may be the same as or different from each other, when b52 is 2 or more, at least two L 52 may be the same as or different from each other, and when b53 is 2 or more, at least two L 53 may be the same as or different from each other. In some embodiments, b51 to b53 can each independently be 1 or 2.
[0247] In Formula 1, Formula 1-1, Formula 1-2, and Formula 2, L1, L7, and L 51 to L 53 may each independently be:
[0248] a single bond; or
[0249] each independently phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, cyclopentadienyl, furanyl, thiophenyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzosilolyl, dibenzosilolyl, azaf luorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasiline group, dibenzothiasiline group, dibenzodihydroazasiline group, dibenzodihydrodisilasiline group, dibenzodihydrodisilasiline group, dibenzodioxane group, dibenzooxathiepin group, dibenzoxazine group, dibenzopyran group, dibenzodithiepin group, dibenzothiazine group, dibenzothiopyran group, dibenzocyclohexadiene group, dibenzodihydropyridine group, or dibenzodihydropyrazine group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 alkyl, C1-C 20alkyl, C1-C6alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazinyl, or triazinyl. 31 31 31 32 33 31 32 31 32 31 32 31 31 31 32
[0250] wherein Q 31 to Q 33 may each independently be hydrogen, deuterium, C1-C6alkyl, C1-C6alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazinyl, or triazinyl. 20 20
[0251] In some embodiments, in Formula 2, the bond between L 51 and R 51 , the bond between L 52 and R 52 , the bond between L 53 and R 53 , the bond between at least two L 51 , the bond between at least two L 52 , the bond between at least two L 53 , the bond between L 51 and X 54 and X 55 in Formula 2, the bond between L 52 and X 54 and X 56 in Formula 2, and the bond between L 53 and X 55 and X 56 in Formula 2, can each be a “carbon-carbon single bond”.
[0252] In Formula 2, X 54 may be N or C(R 54 ), X55 may be N or C(R 55 ), X 56 may be N or C(R 56 ), and is selected from at least one of X 54 to X 56 may be N, wherein R 54 to R 56 may each be understood by reference to the description of R 54 to R 56 provided herein. In some embodiments, two or three of X 54 to X 56 may each be N.
[0253] In this specification, R 51 to R 56 , R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a , and R 84b , R 500a , R 500b , R 501 to R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a , and R 508b may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Arylthioyl, -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 can be understood by referring to the descriptions of Q1 to Q3 provided in this document.
[0254] In some embodiments, i) in Formula 1, R1 to R5, R... are groups other than those represented by Formula 1-1 and Formula 1-2. 5a and R 5b ii) In Equations 1-1 and 1-2, R7 to R9; iii) R in Equations 2, 3-1 to 3-5, 502 and 503. 51 To R 56 R 71 To R 74 R 81 To R 85 R 82a R 82b R 83a R 83b R 84a R 84b R 500a R 500b R 501 To R 508 R 505a R 505b R 506a R 506b R 507a R 507b R 508a and R 508b , and iv)R 10a Each can be independently:
[0255] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 Alkoxy;
[0256] Each of the following C1-C is replaced 20 Alkyl or C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;
[0257] Each of the following is independently unsubstituted or substituted: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrroloyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxolinyl, quinazolinyl, quinazolinyl, carbazole, phenanthrolyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzoxoxazolyl Azolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzosilicyclopentadienyl or groups represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, indazole, purine, quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benz[a]iso[a] Quinolinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiaphene, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, -O(Q) 31 -S(Q) 31 ), -Si(Q 31 (Q) 32 (Q) 33-N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof; or
[0258] -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),
[0259] Among them, Q1 to Q3 and Q 31 To Q 33 Each can be independently:
[0260] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2;
[0261] Each of the following groups, independently unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, or triazinyl: deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, or any combination thereof:
[0262] Formula 91
[0263]
[0264] In Equation 91,
[0265] CY 91 To CY 92 Each can be independently unsubstituted or by at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic groups,
[0266] X 91may be a single bond, O, S, N(R 91 ), 91 ), 91a ), 91b ), 91a ), 91b ,
[0267] R 91 , R 91a , and R 91b may each be understood by reference to the description provided herein for R 82 , R 82a , and R 82b ,
[0268] R 10a may be understood by reference to the description provided herein for R 10a , and
[0269] * indicates a bonding site to an adjacent atom.
[0270] In some embodiments, in Formula 91,
[0271] Ring CY 91 and Ring CY 92 may each independently be phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or triazinyl, each independently unsubstituted or substituted with at least one R 10a ,
[0272] R 91 , R 91a , and R 91b may each independently be:
[0273] hydrogen or C1-C 10 alkyl; or
[0274] phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl, each independently unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof.
[0275] In one or more embodiments, i) in Formula 1, R1to R5, R 5a , and R 5b other than the groups represented by Formula 1-1 and the groups represented by Formula 1-2, ii) in Formula 1-1 and Formula 1-2, R7to R9, iii) R 51 to R 56 , R 71 to R 74 , R 81to R 85 to R 82a to R 82b to R 83a to R 83b to R 84a to R 84b to R 500a to R 500b to R 501 to R 508 to R 505a to R 505b to R 506a to R 506b to R 507a to R 507b to R 508a and R 508b , and iv) R 10a may each independently be hydrogen, deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -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), where Q1to Q3may each be understood by reference to the description of Q1to Q3provided herein:
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282]
[0283] wherein, in Formulae 9-1 to 9-19 and Formulae 10-1 to 10-246, * indicates a bonding site to an adjacent atom, “Ph” represents a phenyl group, and “TMS” represents a trimethylsilyl group.
[0284] In Formulae 3-1 to 3-5, Formula 502, and Formula 503, a71to a74and a501to a504may each indicate R 71 to R 74 and R 501 to R 504The number of R, and a71 to a74 and a501 to a504 can each be independently an integer selected from 0 to 20. When a71 is 2 or greater, at least two R 71 They can be the same or different from each other, and when a72 is 2 or greater, at least two Rs are required. 72 They can be the same or different from each other, and when a73 is 2 or greater, at least two Rs are required. 73 They can be the same or different from each other, and when a74 is 2 or greater, at least two Rs are required. 74 They can be the same or different from each other, and when a501 is 2 or greater, at least two Rs are required. 501 They can be the same or different from each other, and when a502 is 2 or greater, at least two Rs are required. 502 They can be the same or different from each other, and when a503 is 2 or greater, at least two Rs are required. 503 They can be the same or different from each other, and when a504 is 2 or greater, at least two Rs are required. 504 They can be the same or different from each other. a71 to a74 and a501 to a504 can each be an integer selected from 0 to 8 independently.
[0285] In Equation 1, i) the number of a1 is determined by *-(L1). b1 -(R1) c1 At least two of the indicated groups may optionally be linked to each other (via single bond, double bond, or first linking group) to form an unsubstituted or R-shaped group. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 (ii) At least two of the number a2 of the heterocyclic groups R2 may optionally be linked together (via a single bond, double bond or first linking group) to form an unsubstituted or at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 (iii) At least two of the three heterocyclic groups (a3) may optionally be linked together (via a single bond, double bond, or first linking group) to form an unsubstituted or substituted heterocyclic group. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 (iv) At least two of the R4 groups in the number of a4 may optionally be linked to each other (via a single bond, double bond or first linking group) to form an unsubstituted or at least one R4 group. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group.10a Replacement C1-C 60 Heterocyclic groups, and v)R1 to R5, R 5a and R 5b At least two of them may optionally combine with each other to form an unsubstituted or R-shaped compound. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group. The first linking group may be selected from *-N(R) 95 )-*'、*-B(R 95 )-*'、*-P(R 95 )-*'、*-C(R 95a (R) 95b )-*'、*-Si(R 95a (R) 95b )-*'、*-Ge(R 95a (R) 95b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 95 )=*'、*=C(R 95 )-*'、*-C(R 95a )=C(R 95b )-*', *-C(=S)-*' and *-C≡C-*', and R 95 R 95a and R 95b Each can be understood by referring to the description of R1 provided in this article.
[0286] In some implementations, in Equation 2, *-(L 51 ) b51 -R 51 The group represented and the group composed of *-(L 52 ) b52 -R 52 The group represented may not be phenyl.
[0287] In some implementations, in Equation 2, *-(L 51 ) b51 -R 51 The group represented can be combined with *-(L 52 ) b52 -R 52 The groups represented are the same.
[0288] In one or more embodiments, in Equation 2, by *-(L 51 ) b51 -R51 The group represented and the group composed of *-(L 52 ) b52 -R 52 The groups represented can be different from each other.
[0289] In one or more embodiments, in Equation 2, b51 and b52 can each independently be 1, 2, or 3, L 51 and L 52 Each can be independently independent and not replaced or replaced by at least one R 10a Substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
[0290] In some implementations, in Equation 2, R 51 and R 52 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Arylthio, -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3),
[0291] Q1 to Q3 can each be independently C3-C that has not been replaced or has been replaced by the following: 60 Carbocyclic groups or C1-C 60 Heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl, or any combination thereof.
[0292] In some implementations...
[0293] In equation 2, *-(L 51 ) b51 -R 51 The group represented can be one of the groups represented by formulas CY51-1 to CY51-26.
[0294] In equation 2, *-(L 52 ) b52 -R 52 The represented group may be one of the groups represented by formula CY52-1 to formula CY52-26, and / or
[0295] In equation 2, *-(L 53) b53 -R 53 The group represented by Y can be a group represented by one of formula CY53-1 to CY53-27, -C(Q1)(Q2)(Q3), or -Si(Q1)(Q2)(Q3):
[0296]
[0297]
[0298]
[0299] wherein, in formula CY51-1 to CY51-26, formula CY52-1 to CY52-26, and formula CY53-1 to CY53-27,
[0300] Y 63 may be a single bond, O, S, N(R 63 ), B(R 63 ), C(R 63a )(R 63b ), or Si(R 63a )(R 63b ),
[0301] Y 64 may be a single bond, O, S, N(R 64 ), B(R 64 ), C(R 64a )(R 64b ), or Si(R 64a )(R 64b ),
[0302] Y 67 may be a single bond, O, S, N(R 67 ), B(R 67 ), C(R 67a )(R 67b ), or Si(R 67a )(R 67b ),
[0303] Y 68 may be a single bond, O, S, N(R 68 ), B(R 68 ), C(R 68a )(R 68b ), or Si(R 68a )(R 68b ),
[0304] Y 63 and Y 64 in formula CY51-16 and CY51-17 can not be a single bond at the same time,
[0305] Y in formulas CY52-16 and CY52-17 67 and Y 68 They can not both be single keys.
[0306] R 51a To R 51e R 61 To R 64 R 63a R 63b R 64a and R 64b Each can refer to R 51 To understand from the description, and R 51a To R 51e Each of them is not hydrogen.
[0307] R 52a To R 52e R 65 To R 68 R 67a R 67b R 68a and R 68b Each can refer to R 52 To understand from the description, and R 52a To R 52e Each of them is not hydrogen.
[0308] R 53a To R 53e R 69a and R 69b Each can refer to R 53 To understand from the description, and R 53a To R 53e Each of them may not be hydrogen, and
[0309] * Indicates the binding site with neighboring atoms.
[0310] In some embodiments, R in formulas CY51-1 to CY51-26 and CY52-1 to CY52-26 51a To R 51e and R 52a To R 52e Each can be independently:
[0311] Each of the following is independently unsubstituted or substituted: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrroloyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthrolyl, benzimidazolyl, benzofuranyl, benzothiophene, benziisothiazolyl, benzoxazolyl, benzyl The following groups are listed: isoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzosilazocpentadienyl, or groups represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quin Oxalinyl, quinazolinyl, cyclolinyl, carbazole, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzooxazolyl, benzisothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl or any combination thereof; or
[0312] -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3),
[0313] Q1 to Q3 can each be independently unsubstituted or substituted with one of the following: phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, or triazinyl; deuterium, C1-C. 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, or any combination thereof.
[0314] In equations CY51-16 and CY51-17, i)Y 63 It can be O or S, and Y 64 It can be Si(R)64a ) or ii) Y 64b may be Si(R 63 )(R 63a ), and Y 63b may be O or S,
[0315] In Formula CY52-16 and Formula CY52-17, i) Y 67 may be O or S, and Y 68 may be Si(R 68a )(R 68b ), or ii) Y 67 may be Si(R 67a )(R 67b ), and Y 68 may be O or S.
[0316] In Formula 3-1 to Formula 3-5, L 81 to L 85 may each independently be:
[0317] a single bond; or
[0318] *-C(Q4)(Q5)-* or *-Si(Q4)(Q5)-*; or
[0319] each independently phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, cyclopentadienyl, furanyl, thiophenyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzosilolyl, dibenzosilolyl, azaf luorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, or benzothiadiazy!: 20 deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 alkyl, C1-C 31 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilolyl, dimethyldibenzosilolyl, diphenyldibenzosilolyl, -0(Q 31 ), -S(Q 31 ), -Si(Q31 32 33 31 32 31 32 31 32 31 31 31 32 , or any combination thereof,
[0320] wherein Q4, Q5, and Q 31 to Q 33 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, or triazyl.
[0321] In some embodiments, in Formula 3-1 and Formula 3-2, the group represented by may be a group represented by one of Formula CY71-1(1) to CY71-1(8), and / or
[0322] In Formula 3-1 and Formula 3-3, the group represented by may be a group represented by one of Formula CY71-2(1) to CY71-2(8), and / or
[0323] In Formula 3-2 and Formula 3-4, the group represented by may be a group represented by one of Formula CY71-3(1) to CY71-3(32), and / or
[0324] In Formula 3-3 to Formula 3-5, the group represented by may be a group represented by one of Formula CY71-4(1) to CY71-4(32), and / or
[0325] In Formula 3-5, the group represented by may be a group represented by one of Formula CY71-5(1) to CY71-5(8):
[0326]
[0327]
[0328]
[0329]
[0330] wherein, in formula CY71-1(1) to CY71-1(8), formula CY71-2(1) to CY71-2(8), formula CY71-3(1) to CY71-3(32), formula CY71-4(1) to CY71-4(32), and formula CY71-5(1) to CY71-5(8),
[0331] X 82 to X 85 , L 81 , b81, R 81 and R 85 may be understood by referring to the description of X 82 to X 85 , L 81 , b81, R 81 and R 85 provided herein, respectively,
[0332] X 86 may be a single bond, O, S, N(R 86 ), B(R 86 ), C(R 86a )(R 86b ), or Si(R 86a )(R 86b ),
[0333] X 87 may be a single bond, O, S, N(R 87 ), B(R 87 ), C(R 87a )(R 87b ), or Si(R 87a )(R 87b ),
[0334] In formula CY71-1(2) to CY71-1(4), formula CY71-4(2) to CY71-4(4), formula CY71-4(10) to CY71-4(12), formula CY71-4(18) to CY71-4(20), and formula CY71-4(26) to CY71-4(28), X 86 and X 87 may not be a single bond at the same time,
[0335] X 88 may be a single bond, O, S, N(R 88 ), B(R 88 ), C(R 88a )(R 88b ), or Si(R 88a )(R88b
[0336] X 89 may be a single bond, O, S, N(R 89 ), B(R 89 ), C(R 89a )(R 89b ), or Si(R 89a )(R 89b ),
[0337] In Formula CY71-2(2) to CY71-2(4), Formula CY71-3(2) to CY71-3(4), Formula CY71-3(10) to CY71-3(12), Formula CY71-3(18) to CY71-3(20), Formula CY71-3(26) to CY71-3(28), and Formula CY71-5(2) to CY71-5(4), X 88 and X 89 may not both be a single bond, and
[0338] R 86 to R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a , and R 89b may each be understood by reference to the description of R 81 provided herein.
[0339] Detailed Examples of Compounds
[0340] In some embodiments, the first compound (organometallic compound represented by Formula 1) can include (e.g., can be) at least one of compounds D1 to D315, at least one of compounds 1 to 120, or any combination thereof:
[0341]
[0342]
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350]
[0351]
[0352]
[0353]
[0354]
[0355]
[0356] In one or more embodiments, the second compound can include (e.g., can be) at least one of compounds ETH1 to ETH84:
[0357]
[0358]
[0359]
[0360] In one or more embodiments, the third compound can include (e.g., can be) at least one of compounds HTH1 to HTH52:
[0361]
[0362]
[0363] In one or more embodiments, the fourth compound can include (e.g., can be) at least one of compounds DFD1 to DFD14:
[0364]
[0365] 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 the same as the group represented by .
[0366] In some embodiments, the light-emitting device can satisfy at least one of conditions 1 to 4:
[0367] Condition 1
[0368] the LUMO level (eV) of the third compound > the LUMO level (eV) of the first compound,
[0369] Condition 2
[0370] the LUMO level (eV) of the first compound > the LUMO level (eV) of the second compound,
[0371] Condition 3
[0372] the HOMO level (eV) of the first compound > the HOMO level (eV) of the third compound, and
[0373] Condition 4
[0374] the HOMO level (eV) of the third compound > the HOMO level (eV) of the second compound.
[0375] The HOMO level and the LUMO level of the first compound, the second compound, and the third compound can each be a negative value, and the HOMO level and the LUMO level can be actual measured values according to the method described in Evaluation Example 1 provided herein.
[0376] In one or more embodiments, the absolute value of the difference between the LUMO level of the first compound and the LUMO level of the second compound can be about 0.1 eV or more and about 1.0 eV or less, the absolute value of the difference between the LUMO level of the first compound and the LUMO level of the third compound can be about 0.1 eV or more and about 1.0 eV or less, the absolute value of the difference between the HOMO level of the first compound and the HOMO level of the second compound can be 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or more), and the absolute value of the difference between the HOMO level of the first compound and the HOMO level of the third compound can be 1.25 eV or less (e.g., about 1.25 eV or less and about 0.2 eV or more).
[0377] When the relationship between the LUMO level and the HOMO level satisfies the conditions as described above, a balance between holes and electrons injected into the emission layer can be caused.
[0378] The light-emitting device can have the structure of the first embodiment or the second embodiment:
[0379] Description of the first embodiment
[0380] According to the first embodiment, the first compound can be included in an emission layer in a sandwich layer of a light emitting device, wherein the emission layer can further include a host, the first compound can be different from the host, and the emission layer can emit phosphorescence or fluorescence emitted from the first compound. According to the first embodiment, the first compound can be a dopant or an emitter. In some embodiments, the first compound can be a phosphorescent dopant or a phosphorescent emitter.
[0381] The phosphorescence or fluorescence emitted by the first compound can be blue light.
[0382] The emission layer can further include an auxiliary dopant. The auxiliary dopant can be used to improve the light emitting efficiency of the first compound by effectively (or appropriately) transferring energy to the first compound as a dopant or an emitter.
[0383] The auxiliary dopant can be different from the first compound and the host.
[0384] In some embodiments, the auxiliary dopant can be a compound that emits delayed fluorescence.
[0385] In some embodiments, the auxiliary dopant can be a compound including at least one cyclic group including boron (B) and nitrogen (N) as ring-forming atoms.
[0386] Description of the second embodiment
[0387] According to the second embodiment, the first compound can be included in an emission layer in a sandwich layer of a light emitting device, wherein the emission layer can further include a host and a dopant, the first compound can be different from the host and the dopant, and the emission layer can emit phosphorescence or fluorescence (e.g., delayed fluorescence) emitted from the dopant.
[0388] For example, the first compound in the second embodiment can be used as an auxiliary dopant that transfers energy to the dopant (or emitter) rather than the dopant (or emitter) itself.
[0389] In some embodiments, the first compound in the second embodiment can be used as an emitter and an auxiliary dopant that transfers energy to the dopant (or emitter).
[0390] For example, in the second embodiment, the phosphorescence or fluorescence emitted from the dopant (or emitter) can be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
[0391] The dopant (or emitter) in the second embodiment can be a phosphorescent dopant material (e.g., an organometallic compound represented by Formula 1, an organometallic compound represented by Formula 401, or any combination thereof) or a fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof).
[0392] In the first and second embodiments, the blue light can be blue light having a maximum emission wavelength in a range from about 390 nanometers (nm) to about 500 nm, from about 410 nm to about 490 nm, from about 430 nm to about 480 nm, from about 440 nm to about 475 nm, or from about 455 nm to about 470 nm.
[0393] The auxiliary dopant in the first embodiment can include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0394] The host in the first and second embodiments can be any suitable host material (e.g., a compound represented by Formula 301, a compound represented by 301-1, a compound represented by Formula 301-2, or any combination thereof).
[0395] In some embodiments, the host in the first and second embodiments can be the second compound, the third compound, or any combination thereof.
[0396] In one or more embodiments, the light-emitting device can further include at least one of a first capping layer positioned outside the first electrode and a second capping layer positioned outside the second electrode, and at least one of the first capping layer and the second capping layer can include an organometallic compound represented by Formula 1. The first capping layer and the second capping layer can be respectively understood by referring to the description of the first capping layer and the second capping layer provided herein.
[0397] In some embodiments, the light-emitting device can include:
[0398] a first capping layer positioned outside the first electrode and including an organometallic compound represented by Formula 1;
[0399] a second capping layer positioned outside the second electrode and including an organometallic compound represented by Formula 1; or
[0400] the first capping layer and the second capping layer.
[0401] The expression “(the interlayer and / or the capping layer) includes at least one organometallic compound represented by Formula 1” as used herein can be interpreted to mean “(the interlayer and / or the capping layer) can include one organometallic compound of Formula 1 or two or more different organometallic compounds of Formula 1”.
[0402] For example, the interlayer and / or the capping layer can include only compound D1 as the organometallic compound. In this embodiment, compound D1 can be included in an emission layer of the light-emitting device. In some embodiments, compound D1 and compound D2 can be included as organometallic compounds in the interlayer. In this embodiment, compound D1 and compound D2 can be included in the same layer (e.g., both compound D1 and compound D2 can be included in the emission layer) or in different layers (e.g., compound D1 can be included in the emission layer and compound D2 can be included in the electron transport region).
[0403] The term “interlayer” as used herein refers to a single layer and / or multiple layers located between a first electrode and a second electrode in a light-emitting device.
[0404] According to one or more embodiments, an electronic device can include a light-emitting device. The electronic device can further include a thin-film transistor. In some embodiments, the electronic device can further include a thin-film transistor including a source electrode and a drain electrode, and a first electrode of the light-emitting device can be electrically connected to the source electrode or the drain electrode. The electronic device can further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. The electronic device can be understood by referring to the description of the electronic device provided herein.
[0405] According to one or more embodiments, the organometallic compound can be represented by Formula 1, wherein Formula 1 can be understood by referring to the description of Formula 1 provided herein.
[0406] In the organometallic compound represented by Formula 1, the sum of a1 to a4 can be 1 or more, and at least one of R1, at least one of R2, at least one of R3, at least one of R4, or any combination thereof, in an amount of a1, a2, a3, and a4, respectively, can each independently be a group represented by Formula 1-1 or a group represented by Formula 1-2: b1 -(R1) c1 -(R1)
[0407]
[0408] For example, the organometallic compound represented by Formula 1 can include a group represented by Formula 1-1 and / or a group represented by Formula 1-2.
[0409] The moiety represented by ring CY7in Formula 1-1 and Formula 1-2, the moiety represented by ring CY8in Formula 1-1, and R8and R9in Formula 1-2 can each have a high triplet energy level (e.g., a triplet energy level as high as 0.01 eV). Thus, in Formula 1, energy transfer by metal-to-ligand charge transfer and energy transfer by intramolecular space charge transfer can each be activated. In addition, Formula 1-1 and Formula 1-2 can each have structural rigidity due to ring CY7.
[0410] Thus, an organic light emitting device (e.g., an organic light emitting device) including an organometallic compound represented by Formula 1 (or a first compound represented by Formula 1) can have high color purity, high luminous efficiency, low driving voltage, and long lifetime characteristics.
[0411] In one or more embodiments, the organometallic compound represented by Formula 1 can emit blue light. In some embodiments, the organometallic compound represented by Formula 1 can 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.
[0412] In one or more embodiments, the organometallic compound represented by Formula 1 can have a color purity of a bottom emission CIE x coordinate in a range of about 0.12 to about 0.15, or about 0.13 to about 0.14, and a bottom emission CIE y 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.
[0413] A method of synthesizing the organometallic compound represented by Formula 1 can be easily understood by those skilled in the art by referring to the synthesis examples and embodiments described herein.
[0414] Figure 1 Description of the Drawings
[0415] Figure 1 is a schematic view of an organic light emitting device 10 according to one or more embodiments. The organic light emitting device 10 can include a first electrode 110, a layer 130, and a second electrode 150.
[0416] Hereinafter, a structure of the organic light emitting device 10 according to one or more embodiments and a method of manufacturing the organic light emitting device 10 according to one or more embodiments will be described. Figure 1
[0417] The first electrode 110
[0418] In Figure 1 In some embodiments, the substrate can be additionally positioned under the first electrode 110 or over the second electrode 150. The substrate can be a glass substrate and / or a plastic substrate. The substrate can be a flexible substrate including a plastic having excellent heat resistance and durability, for example, polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0419] The first electrode 110 can be formed by depositing or spraying a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a high work function material in which holes can be easily (or appropriately) injected can be used as the material for the first electrode 110.
[0420] The first electrode 110 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination 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 can be used as the material for forming the first electrode 110.
[0421] The first electrode 110 can have a single layer structure including (e.g., consisting of) a single layer or a multi-layer structure including two or more layers. In some embodiments, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO.
[0422] The interlayer 130
[0423] The interlayer 130 can be on the first electrode 110. The interlayer 130 can include an emission layer.
[0424] The interlayer 130 can further include a hole transport zone between the first electrode 110 and the emission layer, and an electron transport zone between the emission layer and the second electrode 150.
[0425] In addition to various organic materials, the interlayer 130 can further include a metal-containing compound such as an organic metal compound and / or an inorganic material such as a quantum dot, etc.
[0426] The interlayer 130 can include i) at least two emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer positioned between the at least two emission units. When the interlayer 130 includes the at least two emission units and the charge generation layer, the light emitting device 10 can be a tandem light emitting device.
[0427] The hole transport zone in the interlayer 130
[0428] The hole transport zone can have i) a single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a single material, ii) a single layer structure comprising (e.g., consisting of) a single layer comprising (e.g., consisting of) a plurality of different materials, or iii) a multi-layer structure having a plurality of layers comprising a plurality of different materials.
[0429] The hole transport zone can comprise a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, an electron blocking layer (EBL), or any combination thereof.
[0430] For example, the hole transport zone can have a multi-layer 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 the layers of each structure are sequentially stacked on the first electrode 110 in each recited order.
[0431] The hole transport zone can comprise a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0432] Formula 201
[0433]
[0434] Formula 202
[0435]
[0436] wherein, in Formula 201 and Formula 202,
[0437] L 201 to L 204 may each independently be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group,
[0438] L 205 may be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or substituted with at least one R 10a substituted C1-C 20 alkylene, unsubstituted or substituted with at least one R 10a substituted C2-C 20 alkenylene, unsubstituted or substituted with at least one R 10a substituted C3-C 60The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,
[0439] xa1 to xa4 can each be an integer selected from 0 to 5 independently.
[0440] xa5 can be an integer selected from 1 to 10.
[0441] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,
[0442] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups combine with each other to form unsubstituted or substituted compounds with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group, etc.) (e.g., compound HT16 described herein),
[0443] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups combine with each other to form unsubstituted or substituted compounds with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and
[0444] na1 can be an integer selected from 1 to 4.
[0445] In some embodiments, formulas 201 and 202 may each include at least one of the groups represented by formulas CY201 to CY217:
[0446]
[0447] In formulas CY201 to CY217, R 10b and R 10c Each can refer to R 10a To understand from the description, CY201 to ring CY 204 may each independently be a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group, and the hydrogen atoms in formula CY201 to formula CY217 can each independently be unsubstituted or substituted with R 10a .
[0448] In some embodiments, in formula CY201 to formula CY217, ring CY 201 to ring CY 204 may each independently be a phenyl group, a naphthyl group, a phenanthryl group, or an anthryl group.
[0449] In one or more embodiments, formula 201 and formula 202 can each include at least one of the groups represented by formula CY201 to formula CY203.
[0450] In one or more embodiments, formula 201 can include at least one of the groups represented by formula CY201 to formula CY203 and at least one of the groups represented by formula CY204 to formula CY217.
[0451] In one or more embodiments, in formula 201, xa1may be 1, R 201 may be a group represented by any one of formula CY201 to formula CY203, xa2may be 0, and R 202 may be a group represented by any one of formula CY204 to formula CY207.
[0452] In one or more embodiments, formula 201 and formula 202 can each not include the groups represented by formula CY201 to formula CY203.
[0453] In one or more embodiments, formula 201 and 202 can each not include the groups represented by formula CY201 to formula CY203, and include at least one of the groups represented by formula CY204 to formula CY217.
[0454] In one or more embodiments, formula 201 and formula 202 can each not include the groups represented by formula CY201 to formula CY217.
[0455] In some embodiments, the hole transport zone can include one selected from the group consisting of 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 / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), and any combination thereof:
[0456]
[0457]
[0458]
[0459]
[0460]
[0461] The thickness of the hole transport zone can be in the range of about 50 (angstroms) to about 10,000 and in some embodiments, about 100 to about 4,000 When the hole transport zone includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer can be in the range of about 100 to about 9,000 and in some embodiments, about 100 to about 1,000 and the thickness of the hole transport layer can be in the range of about 50 to about 2,000 and in some embodiments, about 100 to about 1,500 When the thickness of the hole transport zone, the hole injection layer, and the hole transport layer are in any of their respective ranges, excellent (or improved) hole transport characteristics can be obtained without a significant increase in driving voltage.
[0462] The emission auxiliary layer can increase light emission efficiency by compensating for a light resonance distance according to a wavelength of light emitted by the emission layer. The electron blocking layer can reduce or eliminate the flow of electrons from the electron transport zone. The emission auxiliary layer and the electron blocking layer can each independently include any of the materials described above.
[0463] p-dopant
[0464] The hole transport zone can include a charge generating material as well as the above-described materials to improve the conductive properties of the hole transport zone. The charge generating material can be substantially uniformly or non-uniformly dispersed (e.g., as a single layer consisting of the charge generating material) in the hole transport zone.
[0465] The charge generating material can include, for example, a p-dopant.
[0466] In some embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be -3.5 eV or less.
[0467] In some embodiments, the p-dopant can include a quinone derivative, a cyano-containing compound, an element EL1 and EL2-containing compound, or any combination thereof.
[0468] Examples of the quinone derivative can include TCNQ and F4-TCNQ, and the like.
[0469] Examples of the cyano-containing compound include HAT-CN and a compound represented by Formula 221, and the like:
[0470]
[0471] Formula 221
[0472]
[0473] wherein, in Formula 221,
[0474] R 221 to R 223 may each independently be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group, and
[0475] R 221 to R 223 may each independently be: each independently substituted with cyano; -F; -Cl; -Br; -I; C1-C 20 alkyl; or any combination thereof. 60 carbocyclic group or C1-C 60 heterocyclic group.
[0476] In the element EL1 and EL2-containing compound, the element EL1 can be a metal, a metalloid, or a combination thereof, and the element EL2 can be a non-metal, a metalloid, or a combination thereof.
[0477] Non-limiting examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb) and / or cesium (Cs); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and / or barium (Ba); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), and osmium (Os)). Cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.) and later transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.); lanthanides (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) and / or lutetium (Lu), etc.), etc.
[0478] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0479] Non-limiting examples of nonmetals may include oxygen (O) and halogens (e.g., F, Cl, Br and I, etc.).
[0480] For example, compounds containing elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides and / or quasi-metal iodides), metal tellurides, or any combination thereof.
[0481] Non-limiting examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3 and / or W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2 and / or V2O5, etc.), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3 and / or Mo2O5, etc.) and rhenium oxides (e.g., ReO3, etc.).
[0482] Non-limiting examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0483] Non-limiting examples of alkali metal halides can include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI, among others.
[0484] Non-limiting examples of alkaline earth metal halides can include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2, among others.
[0485] Non-limiting examples of transition metal halides can include titanium halides (e.g., TiF4, TiCl4, TiBr4, and / or TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, and / or ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, and / or HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, and / or VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, and / or NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, and / or TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, and / or CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, and / or MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, and / or WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, and / or MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, and / or TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, and / or ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, and / or FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, and / or RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, and / or OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, and / or CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, and / or RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, and / or IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, and / or NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, and / or PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, and / or PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, and / or AgI, etc.), and gold halides (e.g., AuF, AuCl, AuBr, and / or AuI, etc.), etc.
[0486] Non-limiting examples of post-transition metal halides can include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, and / or ZnI2, etc.), indium halides (e.g., InI3, etc.), and tin halides (e.g., SnI2, etc.), etc.
[0487] Non-limiting examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3, etc.
[0488] Non-limiting examples of metal halide may include antimony halides (e.g., SbCl5, etc.).
[0489] Non-limiting examples of metal tellurides may include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te and / or Cs₂Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, etc.). FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.) and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.).
[0490] emission layer in interlayer 130
[0491] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer according to the sub-pixels. In one or more embodiments, the emitting layer may have a stacked structure. The stacked structure may include two or more layers selected from red, green, and blue emitting layers. 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 emitting layer may include two or more materials. The two or more materials may include red emitting materials, green emitting materials, or blue emitting materials. 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 a single layer may emit white light.
[0492] In some embodiments, the emission layer can include a host and a dopant (or emitter). In some embodiments, the emission layer can further include an auxiliary dopant to facilitate energy transfer to the dopant (or emitter) in addition to the host and the dopant (or emitter). When the emission layer includes the dopant (or emitter) and the auxiliary dopant, the dopant (or emitter) can be different from the auxiliary dopant.
[0493] The first compound can be used as the dopant (or emitter) or can be used as the auxiliary dopant.
[0494] The amount of the dopant (or emitter) in the emission layer can be in the range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.
[0495] The thickness of the emission layer can be in the range of about 100 to about 1,000 and in some embodiments, about 200 to about 600 When the thickness of the emission layer is in any of these ranges, improved light emitting characteristics can be obtained without a significant increase in driving voltage.
[0496] The host
[0497] The host in the emission layer can include the second compound, the third compound, or any combination thereof.
[0498] In some embodiments, the host can further include a compound represented by Formula 301:
[0499] Formula 301
[0500] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0501] In Formula 301,
[0502] Ar 301 and L 301 may each independently be a C3-C 10a carbocyclic group unsubstituted or substituted with at least one R 60 or a C1-C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
[0503] xb11may be 1, 2, or 3,
[0504] xb1may be an integer selected from 0 to 5,
[0505] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),
[0506] xb21 can be an integer selected from 1 to 5, and
[0507] Q 301 To Q 303 Each can understand it by referring to the description of Q1 provided in this article.
[0508] In some implementations, when xb11 in equation 301 is 2 or greater, at least two Ar 301 It can be linked via a single bond.
[0509] In some embodiments, the body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:
[0510] Formula 301-1
[0511]
[0512] Formula 301-2
[0513]
[0514] wherein, in formula 301-1 to formula 301-2,
[0515] Ring A 301 to Ring A 304 may each independently be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group,
[0516] X 301 may be O, S, N-[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0517] xb22and xb23may each independently be 0, 1, or 2,
[0518] L 301 , xb1and R 301 may each be understood by reference to the description of L 301 , xb1and R 301 provided herein, L 302 to L 304 may each be understood by reference to the description of L 301 provided herein,
[0519] xb2to xb4may each be understood by reference to the description of xb1provided herein, and
[0520] R 302 to R 305 and R 311 to R 314 may each be understood by reference to the description of R 301 provided herein,
[0521] In some embodiments, the host can include an alkaline earth metal complex. For example, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0522] In some embodiments, the host can include one of compounds H1-H124, 9,10- bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)- 1,1'-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:
[0523]
[0524]
[0525]
[0526]
[0527]
[0528]
[0529] In some embodiments, the host can include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.
[0530] The host can include only one type (or class) of compound, or two or more different types (or classes) of compounds. As such, embodiments can be modified in various ways.
[0531] Phosphorescent dopant
[0532] The emissive layer can include the first compound described herein as a phosphorescent dopant.
[0533] In some embodiments, the emissive layer can include the first compound, and when the first compound is used as a co-dopant, the emissive layer can include a phosphorescent dopant.
[0534] The phosphorescent dopant can include at least one transition metal as a central metal.
[0535] The phosphorescent dopant can include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0536] The phosphorescent dopant can be electronically neutral.
[0537] In some embodiments, the phosphorescent dopant can include an organometallic complex represented by formula 401:
[0538] Formula 401
[0539] M(L 401) xc1 (L 402 ) xc2
[0540] wherein, in formula 401,
[0541] M can be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0542] L 401 may be a ligand represented by formula 402, and xc1may be 1, 2, or 3, and when xc1is 2 or more, at least two L 401 may be the same as or different from each other,
[0543] L 402 may be an organic ligand, and xc2may be an integer selected from 0 to 4, and when xc2is 2 or more, at least two L 402 may be the same as or different from each other,
[0544] formula 402
[0545]
[0546] in formula 402,
[0547] X 401 and X 402 may each independently be nitrogen or carbon,
[0548] ring A 401 and ring A 402 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0549] T 401 may be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=* or *=C=*,
[0550] X 403 and X 404 may each independently be a chemical bond (for example, a covalent bond or a coordinate bond), O, S, N(Q 413 ), B(Q 413 ), P(Q413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0551] Q 411 to Q 414 may each be understood by reference to the description of Q1 provided herein,
[0552] R 401 and R 402 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a substituted C1-C 20 alkyl, unsubstituted or substituted with at least one R 10a substituted C1-C 20 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ),
[0553] Q 401 to Q 403 may each be understood by reference to the description of Q1 provided herein,
[0554] xc11and xc12may each independently be an integer selected from 0 to 10, and
[0555] * and *' in formula 402 each indicate a binding site to M in formula 401.
[0556] In one or more embodiments, in formula 402, i) X 401 may be nitrogen, and X 402 may be carbon, or ii) X 401 and X 402 may each be nitrogen.
[0557] In one or more embodiments, when xci in Formula 401 is 2 or greater, at least two L 401 two rings A 401 may optionally be bound via T 402 as a linking group, and / or two rings A 402 may optionally be bound via T 403 as a linking group (see, e.g., compounds PD1-PD4 and PD7). T 402 and T 403 may each be understood by reference to the description of T 401 provided herein.
[0558] L 402 in Formula 401 can be any suitable organic ligand. For example, L 402 may be a halide, a diketonate (e.g., acetylacetonate), a carboxylate (e.g., picolinate), -C(=0), an isonitrile, -CN, or a phosphorus group (e.g., a phosphine and / or a phosphite).
[0559] The phosphorescent dopant can be, for example, one or any combination of compounds PD1-PD25:
[0560]
[0561]
[0562] The fluorescent dopant
[0563] In some embodiments, the emissive layer can include a first compound, and when the first compound is used as an auxiliary dopant, the emissive layer can include a fluorescent dopant.
[0564] In some embodiments, the emissive layer can include a first compound, and when the first compound is used as a phosphorescent dopant, the emissive layer can include an auxiliary dopant.
[0565] The fluorescent dopant and the auxiliary dopant can each independently include an arylamine compound, a styrylamine compound, a boron-containing compound, or any combination thereof.
[0566] In some embodiments, the fluorescent dopant and the auxiliary dopant can each independently include a compound represented by Formula 501:
[0567] Formula 501
[0568]
[0569] wherein, in Formula 501,
[0570] Ar 501 , L 501 to L 503R 501 R 502 R 10a R 60 R 10a R 60 R
[0571] xd1, xd2, and xd3 can each independently be 0, 1, 2, or 3, and
[0572] xd4 can be 1, 2, 3, 4, 5, or 6.
[0573] In some embodiments, in Formula 501, Ar 501 may include fused ring groups (e.g., anthracenyl, 1,2- benzophenanthryl, and / or pyrenyl), where at least three monocyclic groups are fused.
[0574] In some embodiments, xd4 in Formula 501 can be 2.
[0575] In some embodiments, the fluorescent dopant and the auxiliary dopant can each independently include one of compounds FD1-FD36, DPVBi, DPAVBi, or any combination thereof:
[0576]
[0577]
[0578]
[0579] In some embodiments, the fluorescent dopant and the auxiliary dopant can each independently include a fourth compound represented by Formula 502 or Formula 503.
[0580] The electron transport region in the interlayer 130
[0581] The electron transport region can have i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0582] The electron transport region can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or an electron injection layer.
[0583] In some embodiments, the electron transport zone can 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, where the layers of each structure are sequentially stacked in the order of each recited in order on the emissive layer.
[0584] The electron transport zone (e.g., the buffer layer, the hole blocking layer, the electron control layer, and / or the electron transport layer in the electron transport zone) can include a metal-free compound including at least one nitrogen-containing C1-C 60 cyclic group.
[0585] In some embodiments, the electron transport zone can include a compound represented by Formula 601:
[0586] Formula 601
[0587] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0588] wherein, in Formula 601,
[0589] Ar 601 and L 601 may each independently be a C3-C 10a carbocyclic group that is unsubstituted or substituted with at least one R 60 C1-C 10a heterocyclic group that is unsubstituted or substituted with at least one R 60 ,
[0590] xe11may be 1, 2, or 3,
[0591] xe1may be 0, 1, 2, 3, 4, or 5,
[0592] R 601 may be a C3-C 10a carbocyclic group that is unsubstituted or substituted with at least one R 60 C1-C 10a heterocyclic group that is unsubstituted or substituted with at least one R 60 , -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ),
[0593] Q 601 To Q 603 Each can refer to the description of Q1 provided in this article to understand it.
[0594] xe21 can be 1, 2, 3, 4 or 5, and
[0595] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic groups.
[0596] In some implementations, when xe11 in formula 601 is 2 or greater, at least two Ar 601 It can be linked via a single bond.
[0597] In some implementations, in formula 601, Ar 601 It can be a substituted or unsubstituted anthracene group.
[0598] In some embodiments, the electron transport region may include a compound represented by formula 601-1:
[0599] Formula 601-1
[0600]
[0601] In Equation 601-1,
[0602] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), selected from X 614 To X 616 At least one of them can be N,
[0603] L 611 To L 613 Each can refer to the L provided in this article. 601 To understand from the description,
[0604] xe611 to xe613 can each be understood by referring to the description of xe1 provided in this document.
[0605] R 611 To R 613 Each can refer to the R provided in this article. 601 To understand from the description, and
[0606] R 614 to R 616 may each independently be hydrogen, deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group.
[0607] For example, in Formula 601 and Formula 601-1, xe1and xe611to xe613may each independently be 0, 1, or 2.
[0608] The electron transport zone can include one of compounds ET1to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0609]
[0610]
[0611]
[0612] The thickness of the electron transport zone can be in a range from about 100 to about 5,000 and in some embodiments, about 160 to about 4,000 When the electron transport zone includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be in a range from about 20 to about 1,000 For example, about 30 to about 300 and the thickness of the electron transport layer can be in a range from about 100 to about 1,000 For example, about 150 to about 500 When the thickness of the buffer layer, the hole blocking layer, the electron control layer, and / or the electron transport layer is each in its respective range, excellent (or improved) electron transport characteristics can be obtained without a significant increase in driving voltage.
[0613] In addition to the materials described above, the electron transport region (e.g., an electron transport layer in the electron transport region) can further include a metal-containing material.
[0614] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ion of the alkali metal complex can be a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, or a cesium (Cs) ion. The metal ion of the alkaline earth metal complex can be a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, or a barium (Ba) ion. The ligand coordinated to the metal ion of the alkali metal complex and the alkaline earth metal complex can each independently be a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
[0615] For example, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1 (LiQ) and / or compound ET-D2:
[0616]
[0617] The electron transport region can include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer can directly contact the second electrode 150.
[0618] The electron injection layer can have i) a single-layer structure (e.g., consisting of) a single layer that includes (e.g., consists of) a single material, ii) a single-layer structure (e.g., consisting of) a single layer that includes (e.g., consists of) a plurality of different materials, or iii) a multi-layer structure having a plurality of layers that include a plurality of different materials.
[0619] The electron injection layer can 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.
[0620] The alkali metal can be Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal can be Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal can be Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0621] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound can each be an oxide, a halide (e.g., a fluoride, a chloride, a bromide, and / or an iodide), a telluride, or any combination thereof of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.
[0622] The alkali metal-containing compound can be selected from an alkali metal oxide (such as Li20, Cs20, and / or K20), an alkali metal halide (such as LiF, NaF, CsF, KF, LiI, Nal, Csl, and / or Kl), or any combination thereof. The alkaline earth metal-containing compound can include an alkaline earth metal oxide (such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound can include YbF3, ScF3, Sc203, Y203, Ce203, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In some embodiments, the rare earth metal-containing compound can include a lanthanide telluride. Non-limiting examples of lanthanide tellurides can include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3, among others.
[0623] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex can each include: i) one of the metal ions of the alkali metal, the alkaline earth metal, and the rare earth metal described above, and ii) a ligand bound to the metal ion, such as a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.
[0624] The electron injection layer can 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 can further include an organic material (e.g., a compound represented by Formula 601).
[0625] In some embodiments, the electron injection layer can include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an 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 can be a KI:Yb co-deposited layer and / or a RbI:Yb co-deposited layer, etc.
[0626] 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 can be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0627] The thickness of the electron injection layer can be in a range of about 1 to about 100 and in some embodiments, about 3 to about 90 When the thickness of the electron injection layer is in any of these ranges, excellent (or improved) electron injection characteristics can be obtained without a significant increase in driving voltage.
[0628] The second electrode 150
[0629] The second electrode 150 can be on the interlayer 130. In one or more embodiments, the second electrode 150 can be a cathode as an electron injection electrode. In this embodiment, a material used to form the second electrode 150 can be a material having a low work function, for example, a metal, an alloy, a conductive compound, or any combination thereof.
[0630] The second electrode 150 can 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 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0631] The second electrode 150 can have a single layer structure or a multi-layer structure including two or more layers.
[0632] The capping layer
[0633] The first capping layer can be positioned outside the first electrode 110, and / or the second capping layer can be positioned outside the second electrode 150. In some embodiments, the light-emitting device 10 can 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 the 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 the 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 the order.
[0634] In the light-emitting device 10, light emitted by the emission layer in the interlayer 130 can pass through the first electrode 110, which can be a semi-transmissive electrode or a transmissive electrode, and the first capping layer to the outside. In the light-emitting device 10, light emitted by the emission layer in the interlayer 130 can pass through the second electrode 150, which can be a semi-transmissive electrode or a transmissive electrode, and the second capping layer to the outside.
[0635] The first capping layer and the second capping layer can improve the external light-emitting efficiency according to the principle of constructive interference. Thus, the optical extraction efficiency of the light-emitting device 10 can be increased, thus improving the light-emitting efficiency of the light-emitting device 10.
[0636] The first capping layer and the second capping layer can each include a material having a refractive index (at 589 nm) of 1.6 or more.
[0637] The first capping layer and the second capping layer can 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.
[0638] At least one of the first capping layer and the second capping layer can each independently include one or more selected from a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, and any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound can be optionally 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 can each independently include an amine-containing compound.
[0639] In some embodiments, at least one of the first capping layer and the second capping layer can each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0640] In one or more embodiments, at least one of the first capping layer and the second capping layer can each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0641]
[0642]
[0643] Electronic device
[0644] Light emitting devices can be included in various appropriate electronic devices. In some embodiments, an electronic device including a light emitting device can be an emissive device or an authentication device.
[0645] In addition to a light emitting device, an electronic device (e.g., an emissive device) can further include 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 can be disposed in at least one propagation direction of light emitted from the light emitting device. For example, the light emitted from the light emitting device can be blue light or white light. Light emitting devices can be understood by reference to the description thereof provided herein. In some embodiments, the color conversion layer can include quantum dots.
[0646] An electronic device can include a first substrate. The first substrate can include a plurality of sub-pixel regions, the color filter can include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer can include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.
[0647] A pixel defining film can be located between the plurality of sub-pixel regions to define each sub-pixel region.
[0648] The color filter can further include a plurality of color filter regions and a light blocking pattern between the plurality of color filter regions, and the color conversion layer can further include a plurality of color conversion regions and a light blocking pattern between the plurality of color conversion regions.
[0649] The plurality of color filter regions (and / or the plurality of color conversion regions) can include: a first region emitting first color light; a second region emitting second color light; and / or a third region emitting third color light, and the first color light, the second color light, and / or the third color light can have different maximum emission wavelengths. In some embodiments, the first color light can be red light, the second color light can be green light, and the third color light can be blue light. In some embodiments, the plurality of color filter regions (and / or the plurality of color conversion regions) can each include quantum dots. In some embodiments, the first region can include red quantum dots, the second region can include green quantum dots, and the third region can not include quantum dots. Quantum dots can be understood by reference to the description of quantum dots provided herein. The first region, the second region, and / or the third region can each further include an emitter.
[0650] In some embodiments, the light emitting device can emit first light, the first region can absorb the first light to emit 1-1 color light, the second region can absorb the first light to emit 2-1 color light, and the third region can 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 can each have different maximum emission wavelengths. In some embodiments, the first light can be blue light, the 1-1 color light can be red light, the 2-1 color light can be green light, and the 3-1 color light can be blue light.
[0651] In addition to the light emitting device, the electronic device can further include a thin film transistor. The thin film transistor can include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode or the drain electrode can be electrically connected to one of the first electrode or the second electrode of the light emitting device.
[0652] The thin film transistor can further include a gate electrode and / or a gate insulating film, etc.
[0653] The active layer can include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor.
[0654] The electronic device can further include a packaging unit for sealing the light emitting device. The packaging unit can be positioned between the color filter and / or the color conversion layer and the light emitting device. The packaging unit can allow light to pass from the light emitting device to the outside, and can simultaneously prevent or reduce air and moisture from penetrating into the light emitting device. The packaging unit can be a sealing substrate including a transparent glass and / or plastic substrate. The packaging unit can be a thin film packaging layer including at least one of an organic layer and an inorganic layer. When the packaging unit is a thin film packaging layer, the electronic device can be flexible.
[0655] Depending on the use of the electronic device, one or more functional layers can be provided on the packaging unit in addition to the color filter and / or the color conversion layer. Examples of the functional layer can include a touch screen layer and a polarizing layer, etc. The touch screen layer can be a resistive touch screen layer, a capacitive touch screen layer, or an infrared light beam touch screen layer. The authentication device can be a biometric authentication device that authenticates an individual, for example, according to biometric information (e.g., a fingertip and / or a pupil, etc.).
[0656] In addition to the light emitting device described above, the authentication device can further include a biometric information collection unit.
[0657] The electronic device can be applicable to various appropriate displays, light sources, illuminations, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game machines, medical devices (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiograph recorders, ultrasonic diagnostic devices, endoscope displays), fish finders, various measurement devices, meters (e.g., meters for automobiles, airplanes, ships), and / or projectors, etc.
[0658] Figure 2 and Figure 3 Description
[0659] Figure 2 is a schematic cross-sectional view of a light emitting apparatus according to one or more embodiments.
[0660] Figure 2 An emission apparatus in FIG. 1 can include a substrate 100, a thin film transistor, a light emitting device, and a package unit 300 sealing the light emitting device.
[0661] The substrate 100 can be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 can be on the substrate 100. The buffer layer 210 can prevent or reduce impurities from penetrating through the substrate 100, and can provide a flat surface on the substrate 100.
[0662] The thin film transistor can be on the buffer layer 210. The thin film transistor can include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0663] The active layer 220 can include an inorganic semiconductor such as silicon and / or polysilicon, an organic semiconductor, or an oxide semiconductor, and can include a source region, a drain region, and a channel region.
[0664] A gate insulating film 230 for insulating the active layer 220 and the gate electrode 240 can be on the active layer 220, and the gate electrode 240 can be on the gate insulating film 230.
[0665] An interlayer insulating film 250 can be on the gate electrode 240. The interlayer insulating film 250 can 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.
[0666] The source electrode 260 and the drain electrode 270 can be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 can be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 can be adjacent to the exposed source region and the exposed drain region of the active layer 220.
[0667] Such a thin film transistor can be electrically connected to the light emitting device to drive the light emitting device, and can be protected by a passivation layer 280. The passivation layer 280 can include an inorganic insulating film, an organic insulating film, or a combination thereof. The light emitting device can be on the passivation layer 280. The light emitting device can include a first electrode 110, an interlayer 130, and a second electrode 150.
[0668] The first electrode 110 can be on the passivation layer 280. The passivation layer 280 can not completely cover the drain electrode 270, and can expose a certain (or set) area of the drain electrode 270, and the first electrode 110 can be disposed to connect (e.g., contact) the exposed area of the drain electrode 270.
[0669] The pixel definition film 290 can be on the first electrode 110. The pixel definition film 290 can expose a certain (or set) area of the first electrode 110, and the interlayer 130 can be formed in the exposed area. The pixel definition film 290 can be a polyimide or a polyacrylic organic film. In one or more embodiments, some of the upper layers of the interlayer 130 can extend to the upper portion of the pixel definition film 290 and can be disposed in the form of a common layer.
[0670] The second electrode 150 can be on the interlayer 130, and the capping layer 170 can additionally be formed on the second electrode 150. The capping layer 170 can be formed to cover the second electrode 150.
[0671] The encapsulation unit 300 can be on the capping layer 170. The encapsulation unit 300 can be on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation unit 300 can include an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyformaldehyde, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), an epoxy resin (e.g., an aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of an inorganic film and an organic film.
[0672] Figure 3 is a schematic cross-sectional view of another light emitting apparatus according to one or more embodiments.
[0673] Figure 3 The illustrated emission apparatus can be substantially the same as Figure 2 the illustrated emission apparatus, except that the light blocking pattern 500 and the functional area 400 are additionally located on the encapsulation unit 300. The functional area 400 can be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In some embodiments, the functional area 400 can include a color filter area and a color conversion area. Figure 3 The illustrated light emitting device can be a series light emitting device.
[0674] Manufacturing method
[0675] The layers constituting the hole transport zone, the emitting layer, and the layers constituting the electron transport zone can be formed in the particular zones by using one or more appropriate methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.
[0676] When the layers constituting the hole transport zone, the emitting layer, and the layers constituting the electron transport zone are each independently formed by vacuum deposition, vacuum deposition can be performed at a deposition temperature in the range of about 100 °C to about 500 °C, under a vacuum degree in the range of about 10 -8 tor to about 10 -3 tor, and at a deposition rate in the range of about 0.01 angstrom per second to about tor to about 10
[0677] General definitions of terms
[0678] The term "C3-C 60 carbocyclic group" as used herein refers to a cyclic group consisting only of carbon atoms as ring-forming atoms, and having 3 to 60 ring-forming carbon atoms. The term "C1-C 60 heterocyclic group" as used herein refers to a cyclic group having 1 to 60 ring-forming carbon atoms in addition to heteroatoms that are not carbon atoms. The C3-C 60 carbocyclic group and the C1-C 60 heterocyclic group can each independently be a monocyclic group consisting of one ring or a polycyclic group in which at least two rings are fused. For example, the C1-C 60 heterocyclic group can have a total number of ring-forming atoms in the range of 3 to 60.
[0679] The term "cyclic group" as used herein can include the C3-C 60 carbocyclic group and the C1-C 60 heterocyclic group.
[0680] The term "π-electron-rich C3-C 60 carbocyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=* as a ring-forming moiety. The term "π-electron-deficient C1-C 60 heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and *-N=* as a ring-forming moiety.
[0681] In some embodiments,
[0682] The C3-C 60 carbocyclic group can be i) a T1 group or ii) a group in which at least two T1 groups are fused (e.g., a C3-C 60The carbocyclic group can be a cyclopentadienyl group, adamantyl group, norbornyl group, phenyl group, pentalenyl group, naphthyl group, azulene group, indacene group, acenaphthene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, 1,2- benzophenanthrene group, perylene group, pentaphene group, heptalene group, naphthacene group, chrysene group, hexacene group, pentacene group, rubicene group, coronene group, ovalene group, indenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, indenophenanthrene group, or indenoanthracene group,
[0683] C1-C 60 The heterocyclic group can be i) a T2 group, ii) a group in which at least two T2 groups are fused, or iii) a group in which at least one T2 group is fused with at least one T1 group (e.g., a C1-C 60 The heterocyclic group can be a pyrrolyl group, thiophenyl group, furanyl group, indolyl group, benzoindolyl group, naphthoindolyl group, isoindolyl group, benzoisoindolyl group, naphthoisoindolyl group, benzosilolyl group, benzothiophenyl group, benzofuranyl group, carbazolyl group, dibenzosilolyl group, dibenzothiophenyl group, dibenzofuranyl group, indenocarbazolyl group, indolocarbazolyl group, benzofuranocarbazolyl group, benzothienocarbazolyl group, benzosilolocarbazolyl group, benzoindolocarbazolyl group, benzocarbazolyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzonaphthosilolyl group, benzofuranodibenzofuranyl group, benzofuranodibenzothiophenyl group, benzothienodibenzothiophenyl group, pyrazolyl group, imidazolyl group, triazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzopyrazolyl group, benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, benzoisothiazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, benzoisoquinolyl group, quinoxalyl group, benzoquinoxalyl group, quinazolyl group, benzoquinazolyl group, phenanthrolinyl group, cinnolinyl group, phthalazinyl group, naphthidinyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, azacarbazolyl group, azaf luorenyl group, azadibenzosilolyl group, azadibenzothiophenyl group, and / or azadibenzofuranyl group, etc.
[0684] The π-electron rich C3-C 60 The cyclic group can be i) a T1 group, ii) a fused group in which at least two T1 groups are fused, iii) a T3 group, iv) a fused group in which at least two T3 groups are fused, or v) a fused group in which at least one T3 group is fused with at least one T1 group (e.g., a π-electron rich C3-C 60 The cyclic group can be a C3-C 60a carbocyclic group, 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 benzasilolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzasilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a benzofuranodibenzofuranyl group, a benzofuranodibenzothiophenyl group, and / or a benzothienodibenzothiophenyl group, and / or the like, and
[0685] a nitrogen-containing C1-C 60 The cyclic group can be i) a T4 group, ii) a group in which at least two T4 groups are fused, iii) a group in which at least one T4 group is fused with at least one T1 group, iv) a group in which at least one T4 group is fused 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 fused (e.g., a nitrogen-containing C1-C 60 The cyclic group can be a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a benzoisoquinolyl group, a quinoxalyl group, a benzoquinoxalyl group, a quinazolyl group, a benzoquinazolyl group, a phenanthrolinyl group, a cinnolinyl group, a phthalazinyl group, a naphthyridinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, and / or an azadibenzofuranyl group, and / or the like,
[0686] wherein the T1 group can be a cyclopropane group, a cyclobutene 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 phenyl group,
[0687] The T2 group can be furanyl, thiophene, 1H-pyrrole, silycyclopentadienyl, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, aziridinyl, aziboroxadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.
[0688] The T3 group can be furanyl, thiophene, 1H-pyrrole, siliconecyclopentadienyl, or borocyclopentadienyl, and
[0689] The T4 group can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, aziridinyl, aziboryl cyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.
[0690] Based on the structure of the formula to which the term is applied, such as the terms "cyclic group" and "C3-C" used herein. 60 "Carbocyclic group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Cyclic group" can be a group fused with any suitable cyclic group, monovalent group, or polyvalent group (e.g., divalent group, trivalent group, and / or tetravalent group, etc.). For example, depending on the structure of the formula including "phenyl", "phenyl" can be a benzo[a] group, phenyl and / or phenylene, etc., which will be understood by those skilled in the art.
[0691] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups. Divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60arylene, C1-C 60 heteroarylene, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups.
[0692] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched-chain aliphatic hydrocarbon monovalent radical of from 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, t-pentyl, neopentyl, i-pentyl, s-pentyl, 3-pentyl, s-i-pentyl, n-hexyl, i-hexyl, s-hexyl, t-hexyl, n-heptyl, i-heptyl, s-heptyl, t-heptyl, n-octyl, i-octyl, s-octyl, t-octyl, n-nonyl, i-nonyl, s-nonyl, t-nonyl, n-decyl, i-decyl, s-decyl, and t-decyl. As used herein, the term "C1-C 60 alkylene" refers to a divalent radical of identical structure of C1-C 60 alkyl.
[0693] As used herein, the term "C2-C 60 alkenyl" refers to a hydrocarbon radical having at least one carbon-carbon double bond in the middle and / or at either end of a C2-C 60 alkyl. Non-limiting examples thereof include ethenyl, propenyl, and butenyl. As used herein, the term "C2-C 60 alkenylene" refers to a divalent radical of identical structure of C2-C 60 alkenyl.
[0694] As used herein, the term "C2-C 60 alkynyl" refers to a monovalent hydrocarbon radical having at least one carbon-carbon triple bond in the middle and / or at either end of a C2-C 60 alkyl. Non-limiting examples thereof include ethynyl and propynyl. As used herein, the term "C2-C 60 alkynylene" refers to a divalent radical of identical structure of C2-C 60 alkynyl.
[0695] As used herein, the term "C1-C 60 alkoxy" refers to a monovalent radical represented by -OA 101 (wherein A 101 is C1-C1alkyl). Non-limiting examples thereof include methoxy, ethoxy, and isopropoxy.
[0696] As used herein, the term "C3-C 10 cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic radical including 3 to 10 carbon atoms. As used herein, C3-C 10Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornelyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl). The term "C3-C" as used herein is also relevant. 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have the same divalent structure.
[0697] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent cyclic group comprising at least one heteroatom other than a carbon atom as a cyclic atom and having 1 to 10 carbon atoms. Non-limiting examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with the same structure.
[0698] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a non-aromatic monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring. Non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" is also relevant. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.
[0699] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group comprising at least one heteroatom other than a carbon atom as a cyclic atom, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.
[0700] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. For example, the term "C6-C" as used herein... 60 "Aspartic" refers to C6-C 60 Aryl groups have the same divalent structure. (C6-C) 60Non-limiting examples of aryl groups include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2- benzophenanthryl, perylenyl, pentaphenyl, heptalenyl, naphthacene, coronene, hexacene, pentacene, and ovalenyl. When C6-C 60 Aryl and C6-C 60 When arylene groups each independently include two or more rings, the individual rings can be fused.
[0701] The term "C1-C60" as used herein refers to a group having from 1 to 60 carbon atoms. The term "C1-C60" as used herein refers to a group having from 1 to 60 carbon atoms. 60 Heteroaryl" refers to a monovalent radical having a heterocyclic aromatic system further including at least one heteroatom in addition to carbon atoms as ring-forming atoms and 1 to 60 carbon atoms. The term "C1-C60" as used herein refers to a group having from 1 to 60 carbon atoms. 60 Heteroarylene" refers to a divalent radical having the same structure as a C1-C 60 Heteroaryl" refers to a monovalent radical having a heterocyclic aromatic system further including at least one heteroatom in addition to carbon atoms as ring-forming atoms and 1 to 60 carbon atoms. The term "C1-C60" as used herein refers to a group having from 1 to 60 carbon atoms. 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. When C1-C 60 Heteroaryl and C1-C 60 When arylene groups each independently include two or more rings, the individual rings can be fused.
[0702] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group having two or more fused rings and only carbon atoms as ring-forming atoms (e.g., 8 to 60 carbon atoms), wherein the overall molecular structure (as a whole) is non-aromatic. Non-limiting examples of monovalent non-aromatic fused polycyclic groups include indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, indenophenanthryl, and indenoanthracenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.
[0703] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more fused rings and at least one heteroatom as a ring-forming atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), wherein the overall molecular structure (as a whole) is non-aromatic. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include pyrrolyl, thienyl, furanyl, indolyl, benzoindolyl, naphthoindolyl, isoindolyl, benzoisoindolyl, naphthoisoindolyl, benzosilolyl, benzothienyl, benzofuranyl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuranyl, azacarbazolyl, azafuoranyl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthosilolyl, benzofuranodibenzofuranyl, benzofuranodibenzothienyl, and benzothienodibenzothienyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having essentially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0704] The term "C6-C 60 aryloxy" refers to a monovalent group represented by -OA 102 wherein A 102 is C6-C 60 aryl. The term "C6-C 60 arylsulfinyl" refers to a monovalent group represented by -SA 103 wherein A 103 is C6-C 60 aryl.
[0705] The term "R 10a " as used herein can be:
[0706] deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;
[0707] each independently C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof;
[0708] Each of the following C3-Cs independently, without being replaced or replaced by others. 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or
[0709] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q)32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) or -P(=O)(Q 31 (Q) 32 ).
[0710] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, or any combination thereof 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkyl groups; or each independently unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C substituted with alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, or any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.
[0711] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Non-limiting examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0712] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "tert-Bu" or "Bu" refers to ethyl. t “” indicates tert-butyl, “OMe” indicates methoxy as used herein, and “D” indicates deuterium as used herein.
[0713] As used herein, the term "biphenyl" refers to a phenyl group that has been substituted with at least one phenyl group. "Biphenyl" belongs to the group with a "C6-C" substituted phenyl group. 60 "Aryl" is "substituted phenyl" as a substituent.
[0714] As used herein, the term "terphenyl" refers to a phenyl group substituted with at least one biphenyl group. "Terphenyl" belongs to the group that has a C6-C substituted phenyl group. 60C6-Ci2-alkyl substituted aryl 60 "Aryl" as a substituent of "substituted phenyl".
[0715] Unless otherwise defined, the symbols *,'and " as used herein refer to the binding site with the adjacent atom in the respective formula.
[0716] Hereinafter, the compounds and light-emitting devices according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The phrase "use B instead of A" used in the Synthesis Examples means that the amount of B used is equal to the amount of A used in terms of molar equivalents.
[0717] Examples
[0718] Synthesis Example 1 (Synthesis of Compound D6)
[0719]
[0720] Synthesis of Intermediate D6-1
[0721] A mixture of 25.0 g (70.8 mmol) of 9-(4-bromopyridin-2-yl)-2-methoxy-9H-carbazole and 700 mL of tetrahydrofuran was cooled to -78°C, and to this was added 39 mL of n-BuLi solution (2.0 molar (M) in hexane), followed by stirring at the same temperature for 1 hour. 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 completed, a NaHCO3 solution was added thereto, and the organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with a 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.
[0722] Synthesis of Intermediate D6-2
[0723] A mixture of 22.3 g (52.5 mmol) of Intermediate D6-1 and 21.0 g (157.5 mmol) of AlCl3 was stirred with an excess of benzene at room temperature for 24 hours under a nitrogen atmosphere. Once the reaction was completed, a NaHCO3 solution was added thereto for neutralization, and the organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with a 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.
[0724] Synthesis of Intermediate D6-3
[0725] Intermediate D6-2 was suspended in excess of a hydrobromic acid solution, then the temperature was raised to 110°C and stirred for 24 hours. Once the reaction was complete, the temperature was lowered to room temperature and a suitable amount of NaHC03 was added for neutralization. Then, 300 mL of distilled water was added and the organic layer was extracted using ethyl acetate and the extracted organic layer was washed using saturated aqueous sodium chloride solution, then dried using MgS04. The resulting product was subjected to column chromatography to thereby obtain 18.9 g (39.5 mmol) of intermediate D6-3.
[0726] Synthesis of intermediate D6-4
[0727] Intermediate D6-3, 8.2 g (34.6 mmol) of 1,3-dibromobenzene, 13.9 g (65.4 mmol, 2.0 eq.) of K3P04, 0.6 g (3.3 mmol, 0.1 eq.) of Cul and 1.3 g (3.3 mmol) of bis([1,1'-biphenyl]-2-yl)oxalamide were added to a reaction vessel and the mixture was suspended in 80 mL of dimethyl sulfoxide, then the temperature was raised to 160°C and stirred for 12 hours. Once the reaction was complete, the temperature was lowered to room temperature and 300 mL of distilled water was added. Then, the organic layer was extracted using ethyl acetate and the extracted organic layer was washed with saturated NaCl aqueous solution, then dried using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 16.5 g (26.3 mmol) of intermediate D6-4.
[0728] Synthesis of intermediate D6-5
[0729] Intermediate D6-4, 15.8 g (45.7 mmol) of N 1 -([1,1':3',1"-terphenyl]-2'-yl-2,2",3,3",4,4",5,5",6,6"-d 10 )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 NaO tBu was added to the reaction vessel and the mixture was suspended in 100 mL of toluene (0.1 M) before the temperature was raised to 120 °C and stirred for 4 hours. Once the reaction was complete, the temperature was lowered to room temperature and 300 mL of distilled water was added to it. Then, the organic layer was extracted from it using ethyl acetate and the extracted organic layer was washed with saturated NaCl aqueous solution before 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.
[0730] Synthesis of intermediate D6-6
[0731] To the reaction vessel were added 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%), 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 ethyl ether. Then, the washed solid was dried to thereby obtain 22.5 g (23.4 mmol) of intermediate D6-6.
[0732] Synthesis of intermediate D6-7
[0733] To the reaction vessel were added 21.1 g (22.5 mmol) of intermediate D6-6 and 11.0 g (67.5 mmol, 3.0 eq.) of NH4PF6, and the mixture was suspended in a mixed solution of 100 mL of methanol and 50 mL of water (in a volume ratio of 2:1) before being stirred at room temperature for 24 hours. Once the reaction was complete, the resulting solid was filtered and washed using ethyl ether. Then, the washed solid was dried to thereby obtain 26.0 g (16.8 mmol) of intermediate D6-7.
[0734] Synthesis of compound D6
[0735] To the reaction vessel were added 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, and the temperature was raised to 110 °C before being stirred for 72 hours. Once the reaction was complete, the temperature was cooled to room temperature, 250 mL of distilled water was added to it, and the organic layer was extracted from it using ethyl acetate, and the extracted organic layer was washed with aqueous NaCl and dried using MgSO4. The resulting product was subjected to column chromatography to thereby obtain 5.5 g (5.1 mmol) of compound D6.
[0736] Synthesis Example 2 (Synthesis of compound D12)
[0737]
[0738] Synthesis of intermediate D12-2
[0739] Intermediate D12-2 was obtained in substantially the same manner as in the synthesis of intermediate D6-2 in Synthesis Example 1, except that intermediate D12-1 was used instead of intermediate D6-1.
[0740] Synthesis of intermediate D12-3
[0741] Intermediate D12-3 was obtained in substantially the same manner as in the synthesis of intermediate D6-3 in Synthesis Example 1, except that intermediate D12-2 was used instead of intermediate D6-2.
[0742] Synthesis of intermediate D12-4
[0743] Intermediate D12-4 was obtained in substantially the same manner as in the synthesis of intermediate D6-4 in Synthesis Example 1, except that intermediate D12-3 was used instead of intermediate D6-3.
[0744] Synthesis of intermediate D12-5
[0745] Intermediate D12-5 was obtained in substantially the same manner as in the synthesis of intermediate D6-5 in Synthesis Example 1, except that intermediate D12-4 was used instead of intermediate D6-4.
[0746] Synthesis of intermediate D12-6
[0747] Intermediate D12-6 was obtained in substantially the same manner as in the synthesis of intermediate D6-6 in Synthesis Example 1, except that intermediate D12-5 was used instead of intermediate D6-5.
[0748] Synthesis of intermediate D12-7
[0749] Intermediate D12-7 was obtained in substantially the same manner as in the synthesis of intermediate D6-7 in Synthesis Example 1, except that intermediate D12-6 was used instead of intermediate D6-6.
[0750] Synthesis of compound D12
[0751] Synthesis of compound D12 was obtained in essentially the same manner as the synthesis of compound D6 in Synthesis Example 1, except that intermediate D12-7 was used in place of intermediate D6-7.
[0752] Synthesis Example 3 (Synthesis of compound D27)
[0753]
[0754] Synthesis of intermediate D27-4
[0755] Intermediate D27-4 was obtained in essentially the same manner as the synthesis of intermediate D12-4 in Synthesis Example 2, except that 1,3-dibromo-5-(tert-butyl)benzene was used in place of 1,3-dibromobenzene.
[0756] Synthesis of intermediate D27-5
[0757] Intermediate D27-5 was obtained in essentially the same manner as the synthesis of intermediate D12-5 in Synthesis Example 2, except that intermediate D27-4 was used in place of intermediate D12-4.
[0758] Synthesis of intermediate D27-6
[0759] Intermediate D27-6 was obtained in essentially the same manner as the synthesis of intermediate D12-6 in Synthesis Example 2, except that intermediate D27-5 was used in place of intermediate D12-5.
[0760] Synthesis of intermediate D27-7
[0761] Intermediate D27-7 was obtained in essentially the same manner as the synthesis of intermediate D12-7 in Synthesis Example 2, except that intermediate D27-6 was used in place of intermediate D12-6.
[0762] Synthesis of compound D27
[0763] Synthesis of compound D27 was obtained in essentially the same manner as the synthesis of compound D12 in Synthesis Example 2, except that intermediate D27-7 was used in place of intermediate D12-7.
[0764] Synthesis Example 4 (Synthesis of compound D81)
[0765]
[0766] Synthesis of intermediate D81-4
[0767] Intermediate D81-4 was synthesized in essentially the same manner as the synthesis of Intermediate D6-4 in Synthetic Example 1, except that 3,5-dibromo-6'-phenyl- 1,1':2',1"-terphenyl was used instead of 1,3-dibromobenzene.
[0768] Synthesis of Intermediate D81-5
[0769] Intermediate D81-5 was obtained in essentially the same manner as the synthesis of Intermediate D6-5 in Synthetic Example 1, except that Intermediate D81-4 was used instead of Intermediate D6-4.
[0770] Synthesis of Intermediate D81-6
[0771] Intermediate D81-6 was obtained in essentially the same manner as the synthesis of Intermediate D6-6 in Synthetic Example 1, except that Intermediate D81-5 was used instead of Intermediate D6-5.
[0772] Synthesis of Intermediate D81-7
[0773] Intermediate D81-7 was obtained in essentially the same manner as the synthesis of Intermediate D6-7 in Synthetic Example 1, except that Intermediate D81-6 was used instead of Intermediate D6-6.
[0774] Synthesis of Compound D81
[0775] 5.22 g (3.95 mmol) of Compound D81 was obtained in essentially the same manner as the synthesis of Compound D6 in Synthetic Example 1, except that Intermediate D81-7 was used instead of Intermediate D6-7.
[0776] Synthetic Example 5 (Synthesis of Compound D302)
[0777]
[0778] Synthesis of Intermediate D302-1
[0779] Intermediate D302-1 was obtained in essentially the same manner as the synthesis of Intermediate D6-1 in Synthetic Example 1, except that acetone-d6 was used instead of 2-adamantanone.
[0780] Synthesis of Intermediate D302-2
[0781] Intermediate D302-2 was obtained in essentially the same manner as the synthesis of Intermediate D6-2 in Synthetic Example 1, except that Intermediate D302-1 was used instead of Intermediate D6-1.
[0782] Synthesis of Intermediate D302-3
[0783] Intermediate D302-3 was obtained in essentially the same manner as in the synthesis of Intermediate D6-3 in Synthetic Example 1, except that Intermediate D302-2 was used instead of Intermediate D6-2.
[0784] Synthesis of Intermediate D302-4
[0785] Intermediate D302-4 was obtained in essentially the same manner as in the synthesis of Intermediate D6-4 in Synthetic Example 1, except that Intermediate D302-3 was used instead of Intermediate D6-3.
[0786] Synthesis of Intermediate D302-5
[0787] Intermediate D302-5 was obtained in essentially the same manner as in the synthesis of Intermediate D6-5 in Synthetic Example 1, except that Intermediate D302-4 was used instead of Intermediate D6-4.
[0788] Synthesis of Intermediate D302-6
[0789] Intermediate D302-6 was obtained in essentially the same manner as in the synthesis of Intermediate D6-6 in Synthetic Example 1, except that Intermediate D302-5 was used instead of Intermediate D6-5.
[0790] Synthesis of Intermediate D302-7
[0791] Intermediate D302-7 was obtained in essentially the same manner as in the synthesis of Intermediate D6-7 in Synthetic Example 1, except that Intermediate D302-6 was used instead of Intermediate D6-6.
[0792] Synthesis of Compound D302
[0793] 5.73 g (5.69 mmol) of Compound D302 was obtained in essentially the same manner as in the synthesis of Compound D6 in Synthetic Example 1, except that Intermediate D302-7 was used instead of Intermediate D6-7.
[0794] The compounds synthesized in Synthetic Examples 1 to 5 were identified by 1 H nuclear magnetic resonance (NMR) and matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF MS). The results thereof are shown in Table 1. The synthetic method of compounds other than the compounds synthesized in Synthetic Examples 1 to 5 can be easily understood by those skilled in the art by referring to the above-described synthetic routes and starting materials.
[0795] Table 1
[0796]
[0797]
[0798] Evaluation Example 1
[0799] The 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.
[0800] Table 2
[0801]
[0802]
[0803] Table 3
[0804] Compound No. HOMO (eV) LUMO (eV) D6 -5.26 -2.09 D12 -5.22 -2.22 D27 -5.23 -2.24 D81 -5.25 -2.25 D302 -5.26 -2.14
[0805]
[0806] Evaluation Example 2
[0807] A film 1 having a thickness of 40 nm was prepared by vacuum co-depositing ETH66, HTH29 and D6 on a quartz substrate under a vacuum degree of 10 -7 Here, as to the amounts of the compounds ETH66, HTH29 and D6, the weight ratio of the compound ETH66 to the compound HTH29 was 3:7, and the content of the 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 the synthesis of the film 1, except that the compound D12, D27, D81 or D302 was respectively used instead of the compound D6.
[0808] The emission spectrum of each film was measured by using a Hamamatsu Quantaurus-QY absolute PL quantum yield measurement system equipped with a xenon light source, a monochromator, a photonic multi-channel analyzer and an integrating sphere, and by using a 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 an interval of 10 nm, wherein the spectrum measured at an excitation wavelength of 340 nm was acquired, and the maximum emission wavelength of the dopant included in each film was obtained. The results are shown in Table 4.
[0809] Subsequently, as to the emission quantum yield, the excitation wavelength of the films 1 to 5 was measured by scanning from 320 nm to 380 nm at an interval of 10 nm by using a Quantaurus-QY absolute PL spectrometer (Hamamatsu), wherein the spectrum at an excitation wavelength of 340 nm was acquired to obtain the emission quantum yield (PLQY). The emission quantum yield of the dopant included in each film is shown in Table 4.
[0810] Table 4
[0811] Film No. Film Composition Maximum Emission Wavelength (nm) PLQY (%) 1 ETH66: HTH29: D6 456 93 2 ETH66: HTH29: D12 457 94 3 ETH66: HTH29: D27 458 94 4 ETH66: HTH29: D81 458 95 5 ETH66: HTH29: D302 456 89
[0812]
[0813] Referring to the results of Table 4, it was found that compounds D6, D12, D27, D81 and D302 emit blue light with excellent PLQY.
[0814] Evaluation Example 3
[0815] At room temperature, the PL spectrum of each of Films 1 to 5 was evaluated by using a time-resolved photoluminescence (TRPL) measurement system FluoTime 300 (available from PicoQuant) and a pump source PLS340 (available from PicoQuant, excitation wavelength = 340 nm, spectral width = 20 nm). Then, the wavelength of the main peak in the PL spectrum was determined, and the number of photons emitted at the main peak wavelength of each film was repeatedly measured over time by time-correlated single-photon counting (TCSPC) while a photon pulse (pulse width = 500 picoseconds, ps) was applied to the film by the PLS340, thereby obtaining a TRPL curve that can be used for fitting. Based on the results thus obtained, one or more exponential decay functions were proposed for fitting, thereby obtaining T 衰减 (Ex), i.e., the decay time of each of Films 1 to 5. The results thereof are shown in Table 5. The function used for fitting is as described in Equation 20, and the decay time T decay was taken as T 衰减 (Ex), i.e., the decay time. Here, the same measurement was again repeated in a dark state (i.e., a state in which the pump signal incident on each film was blocked) during the same measurement time as that for obtaining the TRPL curve, thereby obtaining a baseline or a background signal curve that can be used as a baseline for fitting:
[0816] Equation 20
[0817]
[0818] Table 5
[0819] Film No. Film Composition Decay Time (τ) (microseconds, μβ) 1 ETH66: HTH29: D6 2.17 2 ETH66: HTH29: D12 2.05 3 ETH66: HTH29: D27 2.02 4 ETH66: HTH29: D81 2.03 5 ETH66: HTH29: D302 2.31
[0820] Referring to the results of Table 5, it was found that compounds D6, D12, D27, D81 and D302 have excellent decay times.
[0821] Example 1
[0822] As an anode, 15 Ohms per square centimeter (Ω / cm 2 )(1,200 ITO glass substrate (available from Corning Incorporated) of Example 1 was cut into a size of 50 millimeters (mm) x 50 mm x 0.7 mm, was ultrasonically treated in each of isopropyl alcohol and pure water for 5 minutes, was cleaned with ultraviolet rays for 30 minutes, was then cleaned with ozone, and was mounted on a vacuum deposition apparatus.
[0823] 2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 nm, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as "NPB") was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 nm.
[0824] Compound D6 (as a first compound), compound ETH66 (as a second compound), and compound HTH29 (as a third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 400 nm. Here, the content of compound D6 was 10 wt% based on the total weight of the emission layer of 100 wt%, and the weight ratio of compound ETH66 to compound HTH29 was 3:7.
[0825] Compound ETH2 was deposited on the emission layer to form a hole blocking layer having a thickness of 50 nm, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 nm, LiF was vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of 10 nm, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 nm, thereby completing the manufacture of the organic light emitting device.
[0826]
[0827] Examples 2 to 6
[0828] The organic light emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 6 were used instead of the first, second, and third compounds in forming each respective emission layer.
[0829] Evaluation Example 4
[0830] The organic light emitting devices manufactured in Examples 1 to 6 were measured for luminance at 1,000 cd / m 2drive voltage (V), color purity (CIEx, y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm), and lifetime (T 95 ) of each of the light-emitting devices. The results are shown in Table 6 and Table 7. In Table 7, the lifetime (T 95 ) indicates the time (in hours) required for the luminance of each light-emitting device to drop to 95% of its initial luminance. The electroluminescent spectra, luminance-luminous efficiency plots, and time-luminance plots of Examples 1 to 6 are shown in FIGS. Figure 4 , Figure 6 and Figure 7 , respectively.
[0831] Table 6
[0832]
[0833] Table 7
[0834]
[0835]
[0836]
[0837] With reference to the structures of Table 6 and Table 7, it was found that the organic light-emitting devices of Examples 1 to 6, respectively, have excellent drive voltage, color purity, luminous efficiency, color conversion efficiency, and lifetime characteristics, and emit deep blue light.
[0838] Example 7
[0839] An organic light-emitting device was manufactured in essentially the same manner as in Example 1, except that, in forming the emission layer, compound D6 (as a first compound), compound ETH66 (as a second compound), compound HTH29 (as a third compound), and compound DFD1 (as a fourth compound) were vacuum-deposited on the hole transport layer instead of compound D6 (as a first compound), compound ETH66 (as a second compound), and compound HTH29 (as a third compound). Here, the content of compound D6 was 10 wt% based on the total weight of the emission layer of 100 wt%, the content of compound DFD1 was 0.5 wt% based on the total weight of the emission layer of 100 wt%, and the weight ratio of compound ETH66 to compound HTH29 was 3:7.
[0840] Example 8
[0841] An organic light-emitting device was manufactured in essentially the same manner as in Example 7, except that compound DFD2 was used instead of compound DFD1 as a fourth compound.
[0842] Evaluation Example 5
[0843] The organic light-emitting devices manufactured in Examples 7 and 8 were measured for driving voltage (V) at 1,000 cd / m 2 , color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm), and lifetime (T 95 ) at 1,000 cd / m Figure 5 , Figure 6 and Figure 7
[0844] Table 8
[0845]
[0846]
[0847] Table 9
[0848]
[0849]
[0850] Referring to the results of Table 8 and Table 9, it was found that the organic light-emitting devices of Examples 7 and 8, respectively, had excellent driving voltage, color purity, luminous efficiency, color conversion efficiency, and lifetime characteristics, and emitted deep blue light.
[0851] Example 11
[0852] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that compound D6 (as a first compound) and compound HTH29 (as a third compound) were vacuum-deposited on the hole transport layer to form an emission layer having a thickness of 300 , instead of compound D6 (as a first compound), compound ETH29 (as a second compound), and compound HTH66 (as a third compound) used to form an emission layer having a thickness of 400 . Here, the content of compound D6 was 10 wt% based on the total weight of 100 wt% of the emission layer.
[0853] Comparative Example 1
[0854] 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.
[0855] Evaluation Example 6
[0856] The organic light-emitting devices manufactured in Example 11 and Comparative Example 1 were measured for driving voltage (V) at 1,000 cd / m 2 , color purity (CIEx,y), luminous efficiency (cd / A), color conversion efficiency (cd / A / y), maximum emission wavelength (nm), and lifetime (T 95 at room temperature) by using the same methods as those in Evaluation Example 4. The results thereof are shown in Table 10 and Table 11. Electroluminescent spectra, luminance-luminous efficiency graphs, and time-luminance graphs of Example 11 and Comparative Example 1 are shown in Figure 4 , Figure 6 and Figure 7 , respectively.
[0857] Table 10
[0858]
[0859] Table 11
[0860]
[0861]
[0862] Referring to the results of Table 10 and Table 11, it was found that the organic light-emitting device of Example 11 has excellent driving voltage, color purity, luminous efficiency, color conversion efficiency, and lifetime characteristics, and emits deep blue light, compared to Comparative Example 1.
[0863] As is apparent from the foregoing description, the light-emitting device can have excellent driving voltage, current density, high luminous efficiency, and long lifetime, and can be used to manufacture high-quality electronic devices.
[0864] As used herein, the terms "use", "used", and "using" can be considered synonymous with the terms "utilize", "utilized", and "utilizing", respectively.
[0865] In addition, the terms "substantially", "approximately", and similar terms are used as terms of approximation, 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.
[0866] Furthermore, any numerical range recited herein is intended to include all sub-ranges of the same whole number precision subsumed within the recited range. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges, for example, 2.4 to 7.6, 3.1 to 6.4, etc., within the same precision used to recite the range. 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, the applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited in this specification.
[0867] It is to be understood that the 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 being applicable to 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 can be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims and their equivalents.
Claims
1. A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a layer sandwiched between the first electrode and the second electrode, the layer sandwiched comprising an emissive layer, wherein the layer sandwiched further comprises: i) a first compound represented by Formula 1; and the first compound, the second compound, the third compound, and the fourth compound are different from each other: ii) a second compound comprising at least one π-electron deficient nitrogen-containing C1-C 60 the second compound comprising a cyclic group, the third compound comprising a group represented by Formula 3, the fourth compound capable of emitting delayed fluorescence, or any combination thereof, and Formula 1 Formula 3 wherein, in Formula 1, M is platinum, palladium, gold, nickel, silver, or copper, in Formula 1, X1to X4are each independently C or N, in Formula 1, i) the bond between X1and M is a coordinate bond, and ii) one of the bonds between X2and M, between X3and M, and between X4and M is a coordinate bond, and the other two bonds are each a covalent bond, in Formula 1, ring CY1is i) a five-membered ring containing X1, or ii) a five-membered ring containing X1fused with at least one six-membered ring, the five-membered ring containing X1is pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, or thiadiazolyl, the six-membered ring to which the five-membered ring containing X1is fused is phenyl, pyridyl, or pyrimidyl, in Formula 1, ring CY2is phenyl, pyridyl, pyrimidyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzosilolyl, in Formula 1, b1is an integer selected from 1 to 5, In Formula 1, X 31 to X 36 and X 41 to X 44 each independently is C or N, In formula 1, X 51 is *-N(R5)-*, *-B(R5)-*, *-P(R5)-*, *-C(R 5a )(R 5b )-*, *-Si(R 5a )(R 5b )-*, *-Ge(R 5a )(R 5b )-*, *-S-*, *-Se-*, *-O-*, *-C(=O)-*, *-S(=O)-*, *-S(=O)2-*, *-C(R5)=*, *=C(R5)-*, *-C(R 5a )(R 5b )-*, *-C(=S)-* or *-C≡C-*, and each of * and * indicates a binding site to an adjacent atom, In Equation 1, L1 is a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, wherein, in Formula 1, c1is an integer selected from 0 to 5, a1is an integer selected from 0 to 4, a2is an integer selected from 0 to 10, a3is an integer selected from 0 to 6, and a4is an integer selected from 1 to 4, provided that the sum of a1to a4is 1 or more, and at least one of R4in the number of a4is each independently a group represented by Formula 1-1 or a group represented by Formula 1-2, In formula 1, R1to R5, R 5a and R 5b are each independently 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, an unsubstituted or substituted C1-C 10a alkyl group, an unsubstituted or substituted C2-C 60 alkenyl group, an unsubstituted or substituted C2-C 10a alkynyl group, an unsubstituted or substituted C1-C 60 alkoxy group, an unsubstituted or substituted C3-C 10a carbocyclic group, an unsubstituted or substituted C1-C 60 heterocyclic group, an unsubstituted or substituted C6-C 10a aryloxy group, an unsubstituted or substituted C6-C 60 arylthio group, -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, Q2, and Q3are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, an unsubstituted or substituted C1-C 10a alkyl group, an unsubstituted or substituted C2-C 60 alkenyl group, an unsubstituted or substituted C2-C 10a alkynyl group, an unsubstituted or substituted C1-C 60 alkoxy group, an unsubstituted or substituted C3-C 10a carbocyclic group, an unsubstituted or substituted C1-C 60 heterocyclic group, an unsubstituted or substituted C6-C 10a aryloxy group, an unsubstituted or substituted C6-C 60 arylthio group, -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), in Formula 1-1 and Formula 1-2, b7is an integer selected from 1 to 5, In Equations 1-1 and 1-2, L7 is a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, in Formula 1-1 and Formula 1-2, n7is an integer selected from 1 to 5, In Formula 1-1 and Formula 1-2, ring CY7is a C3-C 60 carbocyclic group or C1-C 60 heterocyclic group, in Formula 1-1, ring CY8is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, or bicyclo[2.2.2]octyl, in Formula 1-1 and Formula 1-2, R7to R9are each understood by reference to the description of R1, in Formula 1-1 and Formula 1-2, a7and a8are each independently an integer selected from 0 to 20, in Formula 3, * indicates a binding site with an adjacent atom, In formula 3, ring CY 71 and ring CY 72 each independently is a π-electron rich C3-C 60 cyclic group or pyridyl group, In Formula 3, X 71 is a single bond or a linking group comprising O, S, N, B, C, Si, or any combination thereof, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro; the number of a1 is 1 or 2, and each of the groups represented by *-(L1) b1 -(R1) c1 represents at least two groups represented by *-(L1) 10a substituted C3-C 60 carbocyclic group, or a C1-C 10a substituted C1-C 60 heterocyclic group, at least two of R2in the amount of a2 are optionally bound to form an unsubstituted or substituted C3-C10carbocyclic group, or an unsubstituted or substituted heterocyclic group 10a substituted C3-C 60 carbocyclic group, or an unsubstituted or substituted heterocyclic group 10a substituted C1-C 60 heterocyclic group, at least two of the R3in the amount of a3 are optionally joined to form an unsubstituted or substituted C3-C10carbocyclic or heterocyclic ring 10a substituted C3-C 60 carbocyclic group, or an unsubstituted or substituted C1-C6alkyl group 10a substituted C1-C 60 heterocyclic ring, at least two of the R4in the amount of a4 are optionally bound to form an unsubstituted or substituted C3-C10carbocyclic group, or an unsubstituted or substituted heterocyclic group 10a substituted C3-C 60 carbocyclic group, or an unsubstituted or substituted heterocyclic group 10a substituted C1-C 60 heterocyclic group, R1 to R5, R 5a and R 5b At least two of them may be optionally combined to form an unsubstituted or R-terminated compound. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, and R 10a is: the following compounds are excluded from the third compound: Each of the following C1-C that is independent and has not been replaced or has been replaced by: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof; Each of the following C3-Cs independently, without being replaced or replaced by others. 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy or C6-C 60 Aryl thiols: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently hydrogen; deuterium; -F; -CI; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 alkyl substituted with deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; or C3-C 60 carbocyclic ring or C1-C 60 heterocyclic ring: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof, and 2. The light-emitting device of claim 1, wherein the second compound comprises pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, or any combination thereof.
3. The light-emitting device of claim 1, wherein the layer sandwiched comprises the second compound.
4. The light-emitting device of claim 3, wherein the layer sandwiched further comprises the third compound, the fourth compound, or any combination thereof. 5. The light-emitting device according to claim 1, wherein the fourth compound is a compound including at least one cyclic group including boron and nitrogen as ring-forming atoms.
6. The light-emitting device according to claim 1, wherein the fourth compound includes a fused ring in which at least one third ring is fused to at least one fourth ring, the third ring is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, and the fourth ring is a 1,2-azaborinanyl group, a 1,3-azaborinanyl group, a 1,4-azaborinanyl group, a 1,2-dihydro-1,2-azaborinanyl group, a 1,4-oxaborinanyl group, a 1,4-thiaborinanyl group, or a 1,4-dihydroborinanyl group.
7. The light-emitting device according to claim 1, wherein the interlayer includes the fourth compound.
8. The light emitting device of Claim 1, wherein the emissive layer comprises: i) the first compound; and ii) the second compound, the third compound, the fourth compound, or any combination thereof, and the first compound is used to emit phosphorescence or fluorescence, and the emission layer is used to emit the phosphorescence or the fluorescence emitted from the first compound.
9. The light-emitting device according to claim 1, wherein the first compound is used to emit phosphorescence or fluorescence, and the phosphorescence or the fluorescence is blue light.
10. The light emitting device of Claim 1, wherein, In Formulae 1-1 and 1-2, ring CY7 is i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings are fused, iv) a fused ring in which at least two second rings are fused, or v) a fused ring in which at least one first ring and at least one second ring are fused, the first ring is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a phenyl group, and the second ring is a pyrrolyl group, a furanyl group, a thiophenyl group, a silolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a 1,2-azaborinanyl group, a 1,3-azaborinanyl group, a 1,4-azaborinanyl group, a 1,2-dihydro-1,2-azaborinanyl group, a 1,4-oxaborinanyl group, a 1,4-thiaborinanyl group, or a 1,4-dihydroborinanyl group.
11. The light emitting device of Claim 1, wherein, In Formula 1-1, ring CY8 is a group represented by one of Formulae CY8-1 to CY8-8: and wherein, in Formulae CY8-1 to CY8-8, * indicates a binding site to an adjacent atom in Formula 1, and *' indicates a binding site to L7 in Formula 1-1.
12. The light-emitting device according to claim 1, wherein the second compound comprises a compound represented by Formula 2: Formula 2 and wherein In Formula 2, L 51 To L 53 Each is independently a single bond, unsubstituted, or affected by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, b51 to b53 are each independently an integer selected from 1 to 5, X 54 is N or C(R 54 ), X 55 is N or C(R 55 ), X 56 is N or C(R 56 ), and at least one of X 54 to X 56 is N, and R 51 To R 56 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Arylthio, -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).
13. The light-emitting device according to claim 1, wherein the third compound comprises a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof: Formula 3-1 Formula 3-2 Formula 3-3 Formula 3-4 Formula 3-5 and wherein, In Formulae 3-1 to 3-5, ring CY 71 to ring CY 74 each independently π-electron rich C3-C 60 cyclic group or pyridyl, X 82 is a single bond, O, S, N-[(L 82 ) b82 -R 82 ], C(R 82a )(R 82b ) or Si(R 82a )(R 82b ), X 83 is a single bond, O, S, N-[(L 83 ) b83 -R 83 ], C(R 83a )(R 83b ) or Si(R 83a )(R 83b ), X 84 is O, S, N-[(L 84 ) b84 -R 84 ], C(R 84a )(R 84b ) or Si(R 84a )(R 84b ), X 85 is C or Si, L 81 to L 85 each independently a single bond, *-C(Q4)(Q5)-*, *-Si(Q4)(Q5)-*, an unsubstituted or substituted pi- electron rich C3-C 10a ring, or an unsubstituted or substituted pyridyl group, wherein Q4and Q5are each understood by reference to the description of Q1, 60 each independently a single bond, *-C(Q4)(Q5)-*, *-Si(Q4)(Q5)-*, an unsubstituted or substituted pi- electron rich C3-C 10a ring, or an unsubstituted or substituted pyridyl group, wherein Q4and Q5are each understood by reference to the description of Q1, b81 to b85 are each independently an integer selected from 1 to 5, and R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic radical, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic radical, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, -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), a71 to a74 are each independently an integer selected from 0 to 20, * and * each indicate a binding site to an adjacent atom.
14. The light-emitting device according to claim 1, wherein the fourth compound is a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof: Formula 502 Formula 503 and wherein, In Formulae 502 and 503, ring A 501 to ring A 504 each independently C3-C 60 carbocyclic group or C1-C 60 heterocyclic group, Y 505 is O, S, N(R 505 ), B(R 505 ), C(R 505a )(R 505b ), or Si(R 505a )(R 505b ), Y 506 is O, S, N(R 506 ), B(R 506 ), C(R 506a )(R 506b ) or Si(R 506a )(R 506b ), Y 507 is O, S, N(R 507 ), B(R 507 ), C(R 507a )(R 507b ) or Si(R 507a )(R 507b ), Y 508 is O, S, N(R 508 ), B(R 508 ), C(R 508a )(R 508b ), or Si(R 508a )(R 508b ), Y 51 and Y 52 each independently B, P(=O), or S(=O), R 500a , R 500b , R 501 to R 508 , R 505a , R 505b , R 506a , R 506b , R 507a , R 507b , R 508a and R 508b are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, -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), and a501 to a504 are each independently an integer selected from 0 to 20.
15. An electronic device comprising the light-emitting device according to any one of claims 1 to 14.
16. The electronic device according to claim 15, further comprising a thin film transistor, wherein the thin film transistor comprises a source electrode and a drain electrode, and the first electrode of the light-emitting device is electrically connected to one of the source electrode or the drain electrode of the thin film transistor.
17. The electronic device of claim 15, further comprising: a color filter, a color conversion layer, a touch screen layer, and / or a polarizing layer.
Citation Information
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Apparatus for Brain Training Service and Driving Method Thereof
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