Light-emitting device including organometallic compound, electronic device including light-emitting device, and organometallic compound
By using organometallic compounds with specific structures as the luminescent layer material, the electrode and sandwich structure are optimized, and the shortcomings in the existing luminescent devices in terms of brightness and life are solved, and an efficient and stable light emission effect is achieved.
Patent Information
- Application Number
- CN202510124064.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-01-26
- Filing Date
- 2025-01-26
- Publication Date
- 2025-07-29
AI Technical Summary
The existing light emitting devices have shortcomings in terms of brightness, luminous efficiency and lifetime, and especially in the light emitting layer using organometallic compounds, it is difficult to achieve efficient and stable light emission.
The organic metal compound represented by formula 1 is used as the material of the light emitting layer, including a combination of specific metal elements and substituent groups, to improve light emission efficiency and stability by optimizing the electrode and sandwich structure.
A light emitting device with high brightness, high luminous efficiency and long life is achieved, and the performance of electronic devices is improved.
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Figure CN120383636A_ABST
Abstract
Description
[0001] Cross - reference to related applications
[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2024 - 0012670, filed with the Korean Intellectual Property Office on January 26, 2024, the entire contents of which are incorporated herein by reference. Technical field
[0003] One or more embodiments of the present disclosure relate to a light - emitting device including an organometallic compound, an electronic device including the light - emitting device, and an organometallic compound. Background art
[0004] In a light - emitting device, a self - emitting device (e.g., an organic light - emitting device) has a relatively wide viewing angle, high contrast, short response time, and excellent or appropriate characteristics in terms of brightness, driving voltage, and response speed.
[0005] The light - emitting device may have the following structure, in which a first electrode is located on a substrate, and a hole - transport region, an emission layer, an electron - transport region, and a second electrode are sequentially stacked on the first electrode in the recited order. Holes provided by the first electrode may move toward the emission layer through the hole - transport region, and electrons provided by the second electrode may move toward the emission layer through the electron - transport region. Charge carriers, such as holes and electrons, may recombine in the emission layer to generate excitons. These excitons may transition from an excited state and decay to a ground state, thereby generating light. Summary of the invention
[0006] One or more aspects of embodiments of the present disclosure relate to a light - emitting device including an organometallic compound, an electronic device including the light - emitting device, and an organometallic compound.
[0007] Additional aspects will be set forth in part in the following description and in part will be obvious from the description, or may be learned by practice of the embodiments presented herein.
[0008] According to one or more embodiments of the present disclosure, a light - emitting device includes:
[0009] A first electrode;
[0010] A second electrode facing the first electrode;
[0011] A sandwich layer between the first electrode and the second electrode and including an emission layer; and
[0012] An organometallic compound represented by Formula 1:
[0013] Formula 1
[0014]
[0015] Among them, in Formula 1,
[0016] M1 can be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm),
[0017] Ring CY1, ring CY2 and ring CY4 can each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0018] X1, X2 and X4 can each independently be C or N,
[0019] Y can be *-C(R6)(R7)-*', *-C(=O)-*', *-C(=S)-*', *-B(R6)-*', *-N(R6)-*', *-O-*', *-P(R6)-*', *-Si(R6)(R7)-*', *-Se-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R6)(R7)-*',
[0020] L1 to L3 can each independently be a single bond, *-C(R 1a )(R 1b )-*', *-C(R 1a )=*', *=C(R 1a )-*', *-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*', *-N(R 1a )-*', *-O-*', *-P(R 1a )-*', *-Si(R 1a )(R 1b )-*', *-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*',
[0021] a1 to a3 can each be an integer selected from 1 to 3,
[0022] * and *' each indicate the binding site to an adjacent atom,
[0023] R1 to R7, R 1a and R 1bEach may independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, 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 C7-C 60 aralkyl, 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), -Ge(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0024] Two or more selected from among a plurality of R1s may optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0025] Two or more selected from among a plurality of R2s may optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0026] Two or more selected from among a plurality of R4s may optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C60 Heterocyclic group
[0027] R6 and R7 are optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group
[0028] b1, b2 and b4 can each independently be an integer selected from 1 to 10
[0029] b3 is 1
[0030] b5 can be an integer selected from 1 to 3
[0031] R 10a can be:
[0032] Deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro
[0033] Each unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(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
[0034] Each unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl, C2-C 60 Heteroarylalkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(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
[0035] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-O(Q 31 )、-S(Q 31 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0036] Q1 to 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; or C1-C unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
[0037] According to one or more embodiments of the present disclosure, an electronic device includes a light-emitting device.
[0038] According to one or more embodiments of the present disclosure, there is provided an organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS
[0039] The accompanying drawings are included to provide a further understanding of the present disclosure, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. The above and other aspects, features and advantages of certain embodiments of the present disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0040] Figure 1 is a schematic diagram of the structure of a light-emitting device according to one or more embodiments of the present disclosure;
[0041] Figure 2 is a schematic diagram of the structure of a light-emitting device according to one or more embodiments of the present disclosure;
[0042] Figure 3 is a schematic diagram of the structure of a light-emitting device according to one or more embodiments of the present disclosure;
[0043] Figure 4 is a schematic perspective view of an electronic device including a light-emitting device according to one or more embodiments of the present disclosure;
[0044] Figure 5 is a schematic diagram of the exterior of a vehicle as an electronic device including a light-emitting device according to one or more embodiments of the present disclosure; and
[0045] Figures 6A to 6C These are schematic views of the interior of a vehicle according to one or more embodiments of the present disclosure. Detailed Embodiments
[0046] One or more embodiments in the accompanying drawings will now be explained in more detail with reference to examples thereof, where the same reference numerals throughout the present disclosure refer to the same elements, and for the sake of brevity, their repeated description may not be provided. In this regard, the presented embodiments may have different forms and should not be construed as limited to the description set forth herein. Accordingly, one or more embodiments are described in more detail only by referring to the accompanying drawings to explain aspects of the present disclosure. As used herein, the term "and / or" or "or" may include any and all combinations of one or more of the associated listed items. Throughout the present disclosure, expressions such as "at least one of...", "one of...", and "selected from...", when before / after a list of elements, modify the entire list of elements, rather than individual elements of the list. For example, "at least one of a, b, and c", "at least one selected from a, b, and c", "at least one selected from a to c", etc., may indicate only a, only b, only c, both a and b (e.g., a and b simultaneously), both a and c (e.g., a and c simultaneously), both b and c (e.g., b and c simultaneously), all of a, b, and c, or variants thereof. Depending on the specific circumstances, " / " used herein may be interpreted as "and" or interpreted as "or".
[0047] According to one or more embodiments of the present disclosure, a light-emitting device may include: a first electrode; a second electrode facing the first electrode; a sandwich layer between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1:
[0048] Formula 1
[0049]
[0050] Wherein, in Formula 1, M1 may be platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).
[0051] According to one or more embodiments, M may be platinum (Pt), palladium (Pd), or gold (Au).
[0052] In Formula 1, ring CY1, ring CY2, and ring CY4 may each independently be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.
[0053] According to one or more embodiments, ring CY1, ring CY2, and ring CY4 may each independently be phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthalenyl, thienyl, furyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzosilolyl, benzogermolyl, benzothienyl, benzoselenophenyl, benzofuryl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzosilolyl, dibenzogermolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuryl, dibenzothiophen-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzosilolyl, azabenzogermolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuryl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzosilolyl, azadibenzogermolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuryl, azadibenzothiophen-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene-5,5-dioxide, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrazinyl, imidazopyrimidinyl, imidazopyridazinyl, 5,6,7,8-tetrahydroisoquinolinyl, or 5,6,7,8-tetrahydroquinolinyl.
[0054] According to one or more embodiments, ring CY1 may be imidazolyl, benzimidazolyl, imidazopyridyl, imidazopyrazinyl, imidazopyrimidinyl, or imidazopyridazinyl.
[0055] According to one or more embodiments, ring CY2 may be phenyl, naphthyl, or 1,2,3,4-tetrahydronaphthalenyl.
[0056] According to one or more embodiments, ring CY4 may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, or isoquinolinyl.
[0057] In Formula 1, X1, X2, and X4 may each independently be C or N.
[0058] According to one or more embodiments, X1 may be C, X2 may be C, and X4 may be N.
[0059] In Formula 1, Y can be *-C(R6)(R7)-*', *-C(=O)-*', *-C(=S)-*', *-B(R6)-*', *-N(R6)-*', *-O-*', *-P(R6)-*', *-Si(R6)(R7)-*', *-Se-*', *-S-*', *-S(=O)-*', *-S(=O)2-* or *-Ge(R6)(R7)-*, where * and *' each indicate a binding site to an adjacent atom.
[0060] According to one or more embodiments, the moiety represented by in Formula 1 can be a group represented by any one selected from Formula CY(1)-1 to Formula CY(1)-12:
[0061]
[0062] wherein, in Formula CY(1)-1 to Formula CY(1)-12,
[0063] R 10 to R 13 can each independently be the same as described herein for R1,
[0064] c10 can be an integer selected from 1 to 4,
[0065] c11 can be an integer selected from 1 to 3,
[0066] c12 can be an integer of 1 or 2, and
[0067] * and *' each indicate a binding site to an adjacent atom.
[0068] According to one or more embodiments, two or more adjacent groups among R 10 and R 11 to R 13 selected from Formula CY(1)-1 to Formula CY(1)-12 can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group.
[0069] According to one or more embodiments, in Formula CY(1)-1 to Formula CY(1)-12, R 13 can be a phenyl, biphenyl or terphenyl group that is each unsubstituted or substituted by at least one R 10a substituent.
[0070] According to one or more embodiments, the moiety represented by in Formula 1 may be a group represented by any one selected from Formula CY(2)-1 to Formula CY(2)-8:
[0071]
[0072] wherein, in Formula CY(2)-1 to Formula CY(2)-8,
[0073] R 21 to R 23 may each independently be the same as described herein for R2, but each may not be hydrogen,
[0074] *, *' and *” each indicate a bonding site to an adjacent atom.
[0075] According to one or more embodiments, the moiety represented by in Formula 1 may be a group represented by any one selected from Formula CY(3)-1 to Formula CY(3)-11:
[0076]
[0077] wherein, in Formula CY(3)-1 to Formula CY(3)-11,
[0078] R3, R5 and b5 may each be the same as described herein,
[0079] Z1 may be the same as described herein for R6,
[0080] Z2 may be the same as described herein for R7,
[0081] Z1 and Z2 may optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0082] Y 11 may be C, Si or Ge,
[0083] L 11 may be *-C(R 6a )(R 7a )-*', *-C(=O)-*', *-C(=S)-*', *-B(R 6a )-*', *-N(R 6a )-*', *-O-*', *-P(R 6a )-*', *-Si(R 6a )(R7a )-*', -Se-*', -S-*', -S(=O)-*', -S(=O)2-*' or -Ge(R 6a )(R 7a )-*', R 31 , R 32 , R 6a and R 7a may each independently be: hydrogen; or the same as described herein for R 10a described,
[0084] R 6a and R 7a may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 60 heterocyclic group,
[0085] c31 and c32 may each independently be an integer selected from 1 to 4, and
[0086] *, *' and *" each indicate a binding site to an adjacent atom.
[0087] According to one or more embodiments, Z1 and Z2 may each independently be an unsubstituted or deuterium, -F, C1-C 10 alkyl, phenyl or any combination thereof substituted C1-C 10 alkyl or phenyl.
[0088] According to one or more embodiments, the moiety represented by in Formula 1 may be a group represented by any one selected from Formula CY(4)-1 to Formula CY(4)-16:
[0089]
[0090] wherein, in Formula CY(4)-1 to Formula CY(4)-16,
[0091] R 41 to R 44 may each independently be the same as described herein for R4, but they may each not be hydrogen, and
[0092] * and *' each indicate a binding site to an adjacent atom.
[0093] In Formula 1, L1 to L3 may each independently be a single bond, -C(R 1a )(R 1b )-*', -C(R 1a )=*', *=C(R1a )-*', *-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*', *-N(R 1a )-*', *-O-*', *-P(R 1a )-*', *-Si(R 1a )(R 1b )-*', *-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*', or *-Ge(R 1a )(R 1b )-*', where * and *' each indicate the bonding site to an adjacent atom.
[0094] In Formula 1, a1 to a3 can each be an integer selected from 1 to 3.
[0095] In Formula 1, if (for example, when) a1 is 2 or greater, then two or more L1s can be the same as or different from each other, if (for example, when) a2 is 2 or greater, then two or more L2s can be the same as or different from each other, and if (for example, when) a3 is 2 or greater, then two or more L3s can be the same as or different from each other.
[0096] According to one or more embodiments, L1 and L3 can each be a single bond, and L2 can be *-O-*', *-S-*', or *-N(R 1a )-*'.
[0097] In Formula 1, R1 to R7, R 1a and R 1b can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, 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 60A heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C7-C 60 An aralkyl group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 An aryloxy group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 An arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2). R 10a and Q1 to Q3 can each be the same as those described herein.
[0098] According to one or more embodiments, R1 to R7, R 1a and R 1b can each independently be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl or C1-C 20 alkoxy;
[0099] C1-C 20 alkyl or C1-C 20 alkoxy each substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl or pyrimidinyl;
[0100] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl , benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: 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, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl , quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -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 ) or -P(=O)(Q 31 )(Q 32 );or
[0101] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), and
[0102] Q1 to Q3 and Q 31 to Q 33 may each independently be:
[0103] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or
[0104] each unsubstituted or substituted with at least one of deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and triazinyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0105] In formula 1, two or more selected from among a plurality of R1s may optionally be bonded to each other to form an unsubstituted or R-substituted 10a C3-C 60 carbocyclic group or an unsubstituted or R-substituted 10a C1-C 60 heterocyclic group.
[0106] In formula 1, two or more selected from among a plurality of R2s may optionally be bonded to each other to form an unsubstituted or R-substituted 10a C3-C 60 carbocyclic group or an unsubstituted or R-substituted 10a C1-C 60 heterocyclic group.
[0107] In formula 1, two or more selected from among a plurality of R4s may optionally be bonded to each other to form an unsubstituted or R-substituted 10a C3-C 60 carbocyclic group or an unsubstituted or R-substituted 10a C1-C 60 heterocyclic group.
[0108] In formula 1, R6 and R7 may optionally be bonded to each other to form an unsubstituted or R-substituted 10a C3-C 60A carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group.
[0109] In Formula 1, b1, b2 and b4 can each independently be an integer selected from 1 to 10.
[0110] In Formula 1, b3 can be 1.
[0111] In Formula 1, b5 can be an integer selected from 1 to 3.
[0112] According to one or more embodiments, the organometallic compound can be represented by Formula 1-1 or Formula 1-2:
[0113] Formula 1-1
[0114]
[0115] Formula 1-2
[0116]
[0117] Wherein, in Formula 1-1 and Formula 1-2,
[0118] M1, Ring CY2, Ring CY4, X2, X4, Y, L1 to L3, a1 to a3, R2 to R5 and b2 to b5 can each be the same as those described herein,
[0119] R 11 to R 17 can each independently be the same as those described herein for R1.
[0120] In Formula 1-1, two or more adjacent groups selected from R 11 to R 13 can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group.
[0121] In Formula 1-2, two or more adjacent groups selected from R 13 to R 17 can optionally be bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group.
[0122] According to one or more embodiments, R13 may be unsubstituted or substituted by at least one R 10a substituted C 6- C 60 aryl or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heteroaryl.
[0123] According to one or more embodiments, the organometallic compound represented by Formula 1 may be represented by any one selected from Compound 1 to Compound 200:
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139]
[0140]
[0141] The organometallic compound represented by Formula 1 may include a group represented by Formula 1A in the structure represented by Formula 1:
[0142] Formula 1A
[0143]
[0144] The group represented by Formula 1A can enhance the chemical stability of the ligand by introducing substituents at positions 4 and 5 which are the active sites of carbazole, and the substituents at positions 4 and 5 can be bonded to each other to form a ring, thereby causing structural distortion of the ligand to prevent or reduce its interaction with the metal, so that the stability of the organometallic compound represented by Formula 1 can be improved.
[0145] Therefore, by using the organometallic compound represented by Formula 1, an electronic device (e.g., a light-emitting device) having high brightness, high luminous efficiency, and long lifespan can be achieved.
[0146] Those of ordinary skill in the art can identify the synthesis method of the organometallic compound represented by Formula 1 by referring to the synthesis examples and / or embodiments provided in the present disclosure.
[0147] According to one or more embodiments,
[0148] The first electrode of the light-emitting device can be an anode,
[0149] The second electrode of the light-emitting device can be a cathode,
[0150] The interlayer can further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode.
[0151] The hole transport region can include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and
[0152] The electron transport region can include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0153] According to one or more embodiments, the interlayer of the light-emitting device can include the organometallic compound represented by Formula 1.
[0154] According to one or more embodiments, the emission layer of the light-emitting device can include the organometallic compound represented by Formula 1.
[0155] According to one or more embodiments, the emission layer can emit blue light, green light, or red light.
[0156] According to one or more embodiments, the emission layer of the light-emitting device can include a dopant and a host, and the organometallic compound represented by Formula 1 can be included in the dopant. For example, in one or more embodiments, the organometallic compound represented by Formula 1 can act as a dopant.
[0157] According to one or more embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may be in direct contact with the emission layer.
[0158] According to one or more embodiments, the interlayer of the light-emitting device may include: i) a first compound, which is an organometallic compound represented by Formula 1; and ii) a second compound including at least one π-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, wherein the first compound, the second compound, the third compound, and the fourth compound may be different from each other:
[0159] Formula 3
[0160]
[0161] wherein ring CY in Formula 3 71 and ring CY 72 may each independently be a π-rich C3-C 60 cyclic group or a pyridyl group,
[0162] X in Formula 3 71 may be a single bond or a linking group including O, S, N, B, C, Si, or any combination thereof,
[0163] * in Formula 3 indicates the binding site to an adjacent atom in the third compound, and
[0164] Compound CBP and compound mCBP may be excluded from the third compound:
[0165]
[0166] Description of the second to fourth compounds
[0167] The second compound may include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.
[0168] For example, in one or more embodiments, in addition to the first compound, the light-emitting device may further include at least one of the second compound and the third compound.
[0169] In one or more embodiments, in addition to the first compound, the light-emitting device may further include the fourth compound.
[0170] In one or more embodiments, the light-emitting device may include all of the first compound to the fourth compound.
[0171] According to one or more embodiments, the interlayer may include a second compound. In addition to the first compound and the second compound, the interlayer may further include a third compound, a fourth compound, or any combination thereof.
[0172] In one or more embodiments, the fourth compound may be a compound in which the difference (e.g., the absolute value of the difference) between the triplet energy level (eV) and the singlet energy level (eV) of the fourth compound is at least 0 eV but not greater than about 0.5 eV (or at least 0 eV but not greater than about 0.3 eV).
[0173] For example, in one or more embodiments, the fourth compound may be a compound including at least one cyclic group that includes a boron (B) atom and a nitrogen (N) atom each as a ring-forming atom.
[0174] In one or more embodiments, the fourth compound may be a compound containing a C8-C 60 polycyclic group that includes two or more cyclic groups fused while sharing a boron (B) atom (e.g., one is a third ring and the other is a fourth ring).
[0175] According to one or more embodiments, the fourth compound may include a fused ring, where at least one third ring may be fused with at least one fourth ring, e.g., to form a fused ring including four or more rings,
[0176] where the third ring may be cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, adamantyl, norbornenyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl, and
[0177] the fourth ring may be 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.
[0178] According to one or more embodiments, the interlayer may include a fourth compound. In addition to the first compound and the fourth compound, the interlayer may further include a second compound, a third compound, or any combination thereof.
[0179] According to one or more embodiments, the interlayer may include a third compound. For example, the third compound may not include (e.g., may exclude) the compound represented by CBP described herein and / or the compound represented by mCBP described herein.
[0180] According to one or more embodiments, the emissive layer of the laminate may include: i) a first compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof.
[0181] The emissive layer may emit phosphorescence or fluorescence emitted from the first compound. For example, in one or more embodiments, the phosphorescence or fluorescence emitted from the first compound may be blue light.
[0182] For example, in one or more embodiments, the emissive layer of the light-emitting device may include a first compound and a second compound, wherein the first compound and the second compound may form an exciplex.
[0183] In one or more embodiments, the emissive layer of the light-emitting device may include a first compound, a second compound, and a third compound, wherein the second compound and the third compound may form an exciplex.
[0184] In one or more embodiments, the emissive layer in the light-emitting device may include a first compound and a fourth compound, and the fourth compound may be used to improve the color purity, luminous efficiency, and lifetime characteristics of the light-emitting device.
[0185] When at least one compound (e.g., the fourth compound) containing boron (B) atoms and nitrogen (N) atoms each as ring-forming atoms and an organometallic compound represented by Formula 1-1 or Formula 1-2 are included together in the dopant, the organometallic compound represented by Formula 1-1 or Formula 1-2 may be used as a sensitizer. When the organometallic compound represented by Formula 1-1 or Formula 1-2 is used as a sensitizer, the energy of the exciton generated in the emissive layer may be transferred to the organometallic compound represented by Formula 1-1 or Formula 1-2, and then the energy may be transferred from the organometallic compound represented by Formula 1-1 or Formula 1-2 to the remaining other dopant (e.g., the fourth compound), and the remaining other dopant may be used as an emitter.
[0186] According to one or more embodiments, the second compound may include a compound represented by Formula 2:
[0187] Formula 2
[0188]
[0189] wherein, in Formula 2,
[0190] L 61 to L 63 may each independently be a single bond, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0191] b61 to b63 can each independently be an integer selected from 1 to 5,
[0192] X 64 can be N or C(R 64 ), X 65 can be N or C(R 65 ), X 66 can be N or C(R 66 ), and at least one selected from X 64 to X 66 can be N,
[0193] R 61 to R 66 can each be the same as described herein, and
[0194] R 10a can be the same as described herein.
[0195] According to 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:
[0196] Formula 3-1
[0197]
[0198] Formula 3-2
[0199]
[0200] Formula 3-3
[0201]
[0202] Formula 3-4
[0203]
[0204] Formula 3-5
[0205]
[0206] wherein, in Formulas 3-1 to 3-5,
[0207] Ring CY 71 to Ring CY 74 can each independently be a π-electron-rich C3-C 60 cyclic group or pyridyl,
[0208] X 82 can be a single bond, B, O, S, N[(L82 ) b82 -R 82 , C(R 82a )(R 82b ) or Si(R 82a )(R 82b ),
[0209] X 83 can be a single bond, B, O, S, N[(L 83 )( b83 -R 83 , C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0210] X 84 can be B, O, S, N[(L 84 )( b84 -R 84 , C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0211] X 85 can be C or Si,
[0212] L 81 to L 85 can each independently be a single bond, *-C(Q4)(Q5)-*', *-Si(Q4)(Q5)-*', an unsubstituted or at least one R 10a substituted π - electron rich C3 - C 60 cyclic group or an unsubstituted or at least one R 10a substituted pyridyl group, where Q4 and Q5 can each be the same as described herein for Q1,
[0213] b81 to b85 can each independently be an integer selected from 1 to 5,
[0214] R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b can each be the same as described herein,
[0215] a71 to a74 can each independently be an integer selected from 0 to 20, and
[0216] R 10a May be the same as those described herein.
[0217] According to one or more embodiments, the fourth compound may include a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0218] Formula 502
[0219]
[0220] Formula 503
[0221]
[0222] Wherein, in Formula 502 and Formula 503,
[0223] Ring A 501 to Ring A 504 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0224] Y 505 may be O, S, N(R 505 ), B(R 505 ), C(R 505a )(R 505b ), or Si(R 505a )(R 505b ),
[0225] Y 506 may be O, S, N(R 506 ), B(R 506 ), C(R 506a )(R 506b ), or Si(R 506a )(R 506b ),
[0226] Y 507 may be O, S, N(R 507 ), B(R 507 ), C(R 507a )(R 507b ), or Si(R 507a )(R 507b ),
[0227] Y 508 may be O, S, N(R 508 ), B(R 508 ), C(R 508a )(R 508b ), or Si(R 508a )(R 508b),
[0228] Y 51 and Y 52 may each independently be B, P(=O) or S(=O),
[0229] 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 be the same as those described herein,
[0230] a501 to a504 may each independently be an integer selected from 0 to 20, and
[0231] R 10a may be the same as those described herein.
[0232] Descriptions of Formula 2, Formula 3, Formula 502 and Formula 503
[0233] In Formula 2, b61 to b63 respectively indicate the number of L 61 to the number of L 63 and may each be an integer selected from 1 to 5. If (for example, when) b61 is 2 or greater, then two or more L 61 may be the same as or different from each other. If (for example, when) b62 is 2 or greater, then two or more L 62 may be the same as or different from each other, and if (for example, when) b63 is 2 or greater, then two or more L 63 may be the same as or different from each other. For example, in one or more embodiments, b61 to b63 may each independently be 1 or 2.
[0234] In Formula 2, L 61 to L 63 may each independently be:
[0235] a single bond; or
[0236] Each unsubstituted or substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, azafuranyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilacyclohexanyl, dibenzothiasilacyclohexanyl, dibenzodihydroazasilacyclohexanyl, dibenzodihydrodisilacyclohexanyl, dibenzodihydrosilacyclohexanyl, dibenzooxanyl, dibenzothioxolyl, dibenzooxazinyl, dibenzopyranyl, dibenzodithiolanyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridyl or dibenzodihydropyrazinyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, dimethyldibenzosilolyl, diphenyldibenzosilolyl, -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, and
[0237] Q 31 to Q 33 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0238] According to one or more embodiments, in Formula 2, L 61 and R 61 the bond between, L 62 and R 62 the bond between, L 63 and R 63 the bond between, two L 61 the bond between, two L 62 the bond between, two L 63 the bond between, L 61 and the carbon between X 64 and X 65 in Formula 2, the bond between, L 62 and the carbon between X 64 and X 66 in Formula 2, and the bond between L 63 and the carbon between X 65 and X 66 in Formula 2 may each be a "carbon-carbon single bond".
[0239] In Formula 2, X 64 can be N or C(R 64 ), X 65 can be N or C(R 65 ), X 66 can be N or C(R 66 ), and at least one selected from X 64 to X 66 can be N. R 64 to R 66 can each be the same as described herein. For example, in one or more embodiments, two or three selected from X 64 to X 66 can each be N.
[0240] In the present disclosure, R 61 to R 66 , 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 , R506b , R 507a , R 507b , R 508a and R 508b may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, 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). Q1 to Q3 may each be the same as those described herein.
[0241] For example, in one or more embodiments, R 61 to R 66 , 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 , R508a and R 508b may each independently be:
[0242] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl or C1-C 20 alkoxy;
[0243] C1-C alkyl or C1-C alkoxy each substituted with: 20 deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 20 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof; 10 cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C
[0244] alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl, azadibenzosilolyl, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 10 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 20 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl, azadibenzosilolyl, or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 10alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, 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
[0245] -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
[0246] Q1 to Q3 and Q 31 to Q 33 can each independently be:
[0247] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or
[0248] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C1-C 10Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof:
[0249] Formula 91
[0250]
[0251] wherein, in Formula 91,
[0252] Ring CY 91 and Ring CY 92 may each independently be an unsubstituted or at least one R 10a substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 30 heterocyclic group,
[0253] X 91 may be a single bond, O, S, N(R 91 ), B(R 91 ), C(R 91a )(R 91b ), or Si(R 91a )(R 91b ),
[0254] R 91 、R 91a and R 91b may be the same as described herein for R 82 、R 82a and R 82b respectively,
[0255] R 10a may be the same as described herein, and
[0256] * indicates the binding site to an adjacent atom.
[0257] For example, in one or more embodiments, in Formula 91,
[0258] Ring CY 91 and Ring CY 92 may each independently be an unsubstituted or at least one R 10a substituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or triazinyl, and
[0259] R 91 、R 91a and R 91b may each independently be:
[0260] hydrogen or C1-C 10 alkyl; or
[0261] Each unsubstituted or substituted phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl group: deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0262] According to one or more embodiments, R in Formula 2, Formulas 3-1 to 3-5, Formula 502 and Formula 503 61 to R 66 、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 may each independently be:
[0263] hydrogen, deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one selected from Formulas 9-1 to 9-19, a group represented by one selected from Formulas 10-1 to 10-246, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3) or -P(=O)(Q1)(Q2) (where Q1 to Q3 may each be the same as described herein):
[0264]
[0265]
[0266]
[0267]
[0268]
[0269]
[0270] Among formulas 9-1 to 9-19 and formulas 10-1 to 10-246, * indicates a binding site to an adjacent atom, "Ph" represents a phenyl group, "D" represents deuterium, and "TMS" represents a trimethylsilyl group.
[0271] In formulas 3-1 to 3-5, formula 502, and formula 503, a71 to a74 and a501 to a504 each respectively indicate the number of R 71 to R 74 and the number of R 501 to R 504 and can each independently be an integer selected from 0 to 20. If (for example, when) a71 is 2 or greater, then two or more R 71 can be the same as or different from each other. If (for example, when) a72 is 2 or greater, then two or more R 72 can be the same as or different from each other. If (for example, when) a73 is 2 or greater, then two or more R 73 can be the same as or different from each other. If (for example, when) a74 is 2 or greater, then two or more R 74 can be the same as or different from each other. If (for example, when) a501 is 2 or greater, then two or more R 501 can be the same as or different from each other. If (for example, when) a502 is 2 or greater, then two or more R 502 can be the same as or different from each other. If (for example, when) a503 is 2 or greater, then two or more R 503 can be the same as or different from each other, and if (for example, when) a504 is 2 or greater, then two or more R 504 can be the same as or different from each other. a71 to a74 and a501 to a504 can each independently be an integer selected from 0 to 8.
[0272] In one or more embodiments, in formula 2, the group represented by *-(L 61 ) b61 -R 61 and the group represented by *-(L 62 ) b62 -R 62 may not be a phenyl group.
[0273] According to one or more embodiments, in formula 2, the group represented by *-(L 61 ) b61 -R 61 and the group represented by *-(L 62 ) b62 -R 62 may be the same as each other.
[0274] According to one or more embodiments, in Formula 2, the group represented by *-(L 61 ) b61 -R 61 and the group represented by *-(L 62 ) b62 -R 62 may be different from each other.
[0275] According to one or more embodiments, in Formula 2, b61 and b62 may each be 1, 2, or 3, and L 61 and L 62 may each independently be phenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl that is unsubstituted or substituted with at least one R 10a .
[0276] For example, in one or more embodiments, in Formula 2, R 61 and R 62 may each independently be a C3-C 10a carbocyclic group that is unsubstituted or substituted with at least one R 60 , a C1-C 10a heterocyclic group that is unsubstituted or substituted with at least one R 60 , a C6-C 10a aryloxy group that is unsubstituted or substituted with at least one R 60 , a C6-C 10a arylthio group that is unsubstituted or substituted with at least one R 60 , -C(Q1)(Q2)(Q3), or -Si(Q1)(Q2)(Q3), and
[0277] Q1 to Q3 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group that is unsubstituted or substituted with the following: deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof.
[0278] According to one or more embodiments,
[0279] the group represented by *-(L 61 ) b61 -R 61 in Formula 2 may be a group represented by one selected from Formula CY51-1 to Formula CY51-26, and / or
[0280] the group represented by *-(L 62 ) b62 -R 62The group represented may be a group represented by one selected from Formula CY52-1 to Formula CY52-26, and / or
[0281] In Formula 2, the group represented by *-(L 63 ) b63 -R 63 may be a group represented by one selected from Formula CY53-1 to Formula CY53-27, -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3):
[0282]
[0283]
[0284]
[0285] wherein, in Formula CY51-1 to Formula CY51-26, Formula CY52-1 to Formula CY52-26 and Formula CY53-1 to Formula CY53-27,
[0286] 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 ),
[0287] 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 ),
[0288] 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 ),
[0289] 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 ),
[0290] Y in Formula CY51-16 and Formula CY51-17 63 and Y 64 can each be a single bond differently,
[0291] Y in Formula CY52-16 and Formula CY52-17 67 and Y 68 can each be a single bond differently,
[0292] R 51a to R 51e 、R 61 to R 64 、R 63a 、R 63b 、R 64a and R 64b can each be the same as that described for R in Formula 2 herein, where R 61 to R 51a can each not be hydrogen, 51e
[0293] R 52a to R 52e 、R 65 to R 68 、R 67a 、R 67b 、R 68a 、R 68b and R 68b 62 can each be the same as that described for R in Formula 2 herein, where R 52a to R 52e can each not be hydrogen,
[0294] R 53a to R 53e 、R 69a and R 69b can each be the same as that described for R in Formula 2 herein, where R 63 to R 53a to R 53e can each not be hydrogen, and
[0295] * indicates the binding site to the adjacent atom.
[0296] For example, in one or more embodiments,
[0297] In Formulas CY51-1 to CYTY51-26 and Formulas CY52-1 to CY52-26, R 51a to R 51e and R 52a to R 52e can each independently be:
[0298] Each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl, azadibenzosilolyl or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl or any combination thereof; or
[0299] -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3), and
[0300] Q1 to Q3 may each independently be phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl which is unsubstituted or substituted by: deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof,
[0301] In Formulas CY51-16 and CY51-17, i) Y 63 may be O or S, and Y 64 may be Si(R 64a )(R 64b ), or ii) Y 63 may be Si(R 63a )(R 63b ), and Y 64 may be O or S, and
[0302] In Formulas CY52-16 and 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.
[0303] In one or more embodiments, in Formulas 3-1 to 3-5, L 81 to L 85 may each independently be:
[0304] A single bond;
[0305] *-C(Q4)(Q5)-*' or *-Si(Q4)(Q5)-*'; or
[0306] Phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, cyclopentadienyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, pyridyl, pyrrolyl, benzoxadiazolyl or benzothiadiazolyl, each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, dimethyldibenzosilolyl, diphenyldibenzosilolyl, -O(Q 31 ), -S(Q 31 ), -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q32 )、 -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, and
[0307] Q4, Q5, and Q 31 to Q 33 can each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, or triazinyl.
[0308] In one or more embodiments, the group represented by in Formulas 3-1 and 3-2 can be a group represented by one selected from Formulas CY71-1(1) to CY71-1(8), and / or
[0309] the group represented by in Formulas 3-1 and 3-3 can be a group represented by one selected from Formulas CY71-2(1) to CY71-2(8), and / or
[0310] the group represented by in Formulas 3-2 and 3-4 can be a group represented by one selected from Formulas CY71-3(1) to CY71-3(32), and / or
[0311] the group represented by in Formulas 3-3 to 3-5 can be a group represented by one selected from Formulas CY71-4(1) to CY71-4(32), and / or
[0312] the group represented by in Formula 3-5 can be a group represented by one selected from Formulas CY71-5(1) to CY71-5(8):
[0313]
[0314]
[0315]
[0316]
[0317] Among formulas CY71-1(1) to CY71-1(8), formulas CY71-2(1) to CY71-2(8), formulas CY71-3(1) to CY71-3(32), formulas CY71-4(1) to CY71-4(32), and formulas CY71-5(1) to CY71-5(8),
[0318] X 82 to X 85 、L 81 、b81、R 81 and R 85 may each be the same as those described herein,
[0319] 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 ),
[0320] 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 ),
[0321] In formulas CY71-1(2) to CY71-1(4), formulas CY71-4(2) to CY71-4(4), formulas CY71-4(10) to CY71-4(12), formulas CY71-4(18) to CY71-4(20), and formulas CY71-4(26) to CY71-4(28), each of X 86 and X 87 cannot both be single bonds at the same time,
[0322] X 88 may be a single bond, O, S, N(R 88 ), B(R 88 ), C(R 88a )(R 88b ) or Si(R 88a )(R 88b ),
[0323] 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 ),
[0324] In Formula CY71-2(2) to Formula CY71-2(4), Formula CY71-3(2) to Formula CY71-3(4), Formula CY71-3(10) to Formula CY71-3(12), Formula CY71-3(18) to Formula CY71-3(20), Formula CY71-3(26) to Formula CY71-3(28), and Formula CY71-5(2) to Formula CY71-5(4), X 88 and X 89 can each be different and be single bonds, and
[0325] R 86 to R 89 , R 86a , R 86b , R 87a , R 87b , R 88a , R 88b , R 89a and R 89b can each be the same as those described herein for R 81 .
[0326] Detailed examples of the second to fourth compounds
[0327] According to one or more embodiments, the second compound can include at least one selected from Compound ETH1 to Compound ETH84:
[0328]
[0329]
[0330]
[0331]
[0332] According to one or more embodiments, the third compound can include at least one selected from Compound HTH1 to Compound HTH52:
[0333]
[0334]
[0335]
[0336] According to one or more embodiments, the fourth compound can include at least one selected from Compound DFD1 to Compound DFD12:
[0337]
[0338] In the above compounds, "Ph" represents a phenyl group, "D5" represents being substituted by five deuterium atoms, and "D4" represents being substituted by four deuterium atoms. For example, the group represented by can be substantially the same as the group represented by
[0339] According to one or more embodiments, the light-emitting device may satisfy at least one selected from Condition 1 to Condition 4:
[0340] Condition 1
[0341] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound > the LUMO energy level (eV) of the first compound
[0342] Condition 2
[0343] The LUMO energy level (eV) of the first compound > the LUMO energy level (eV) of the second compound
[0344] Condition 3
[0345] The highest occupied molecular orbital (HOMO) energy level (eV) of the first compound > the HOMO energy level (eV) of the third compound
[0346] Condition 4
[0347] The HOMO energy level (eV) of the third compound > the HOMO energy level (eV) of the second compound.
[0348] The HOMO energy levels and LUMO energy levels of the first compound, the second compound, and the third compound may each be negative values, and the HOMO energy levels and LUMO energy levels may each be: values measured according to an appropriate method; or values evaluated by using a density functional theory (DFT) method.
[0349] According to one or more embodiments, the absolute value of the difference between the LUMO energy level of the first compound and the LUMO energy level of the second compound may be about 0.1 eV or greater and about 1.0 eV or less, or the absolute value of the difference between the LUMO energy level of the first compound and the LUMO energy level of the third compound may be about 0.1 eV or greater and about 1.0 eV or less, and the absolute value of the difference between the HOMO energy level of the first compound and the HOMO energy level of the second compound may be about 1.25 eV or less (for example, about 1.25 eV or less and about 0.2 eV or greater), or the absolute value of the difference between the HOMO energy level of the first compound and the HOMO energy level of the third compound may be about 1.25 eV or less (for example, about 1.25 eV or less and about 0.2 eV or greater).
[0350] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions described above, the balance between holes and electrons in the injection-emission layer can be achieved.
[0351] The light-emitting device may have the structure of the first embodiment or the second embodiment. The first embodiment or the second embodiment may be the same as those described herein.
[0352] Description of the First Embodiment
[0353] According to the first embodiment, a first compound may be included in the emission layer in the sandwich structure of the light-emitting device, where the emission layer may further include a host, the first compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence from the first compound. For example, according to the first embodiment, the first compound may be a dopant or an emitter. For example, the first compound may be a phosphorescent dopant or a phosphorescent emitter.
[0354] The phosphorescence or fluorescence emitted from the first compound may be blue light.
[0355] In one or more embodiments, the emission layer may further include a co-dopant. The co-dopant may be used to improve the luminescence efficiency of the first compound by effectively transferring energy to the first compound as a dopant or an emitter.
[0356] The co-dopant may be different from each of the first compound and the host.
[0357] In one or more embodiments, the co-dopant may be a compound that emits delayed fluorescence.
[0358] In some embodiments, the co-dopant may be a compound including at least one cyclic group that includes boron (B) atoms and nitrogen (N) atoms each as ring-forming atoms.
[0359] Description of the Second Embodiment
[0360] According to the second embodiment, a first compound may be included in the emission layer in the sandwich structure of the light-emitting device, where the emission layer may further include a host and a dopant, the first compound, the host, and the dopant may be different from each other, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.
[0361] For example, in the second embodiment, the first compound may not be used as a dopant, but as a co-dopant that transfers energy to the dopant (or emitter).
[0362] In one or more embodiments, the first compound in the second embodiment may be used as an emitter and also as a co-dopant that transfers energy to the dopant (or emitter).
[0363] For example, in one or more embodiments, the phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).
[0364] The dopant (or emitter) in the second embodiment may be any phosphorescent dopant material (e.g., the organometallic compound represented by Formula 1 described herein, the organometallic compound represented by Formula 401 described herein, or any combination thereof) or any fluorescent dopant material (e.g., the compound represented by Formula 501 described herein, the compound represented by Formula 502 described herein, the compound represented by Formula 503 described herein, or any combination thereof).
[0365] In the first and second embodiments, the blue light may be blue light having a maximum emission wavelength range of about 430 nanometers (nm) to about 490 nm, about 430 nm to about 485 nm, about 440 nm to about 475 nm, or about 455 nm to about 470 nm.
[0366] The co-dopant in the first embodiment may include, for example, the fourth compound represented by Formula 502 or Formula 503 described herein.
[0367] The host in the first and second embodiments may be any host material (e.g., the compound represented by Formula 301 described herein, the compound represented by Formula 301-1 described herein, the compound represented by Formula 301-2 described herein, or any combination thereof).
[0368] In one or more embodiments, the host in the first and second embodiments may be the second compound, the third compound, or any combination thereof.
[0369] According to one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside the first electrode (e.g., on the first electrode) and a second capping layer located outside the second electrode (e.g., on the second electrode), and at least one of the first capping layer and the second capping layer may include an organometallic compound represented by Formula 1-1 or Formula 1-2. More details regarding the first capping layer and / or the second capping layer may be the same as those described herein.
[0370] According to one or more embodiments, the light-emitting device may include:
[0371] A first capping layer, located outside the first electrode (e.g., on the first electrode) and including an organometallic compound represented by Formula 1;
[0372] A second capping layer, located outside the second electrode (e.g., on the second electrode) and including an organometallic compound represented by Formula 1; or
[0373] A first capping layer and a second capping layer.
[0374] As used herein, the phrase “(the interlayer and / or the capping layer) includes an organometallic compound represented by Formula 1” can be understood as “(the interlayer and / or the capping layer) may include one kind of organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds each represented by Formula 1.
[0375] For example, in some embodiments, the interlayer and / or the capping layer may include only Compound 1 as the organometallic compound represented by Formula 1. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include Compound 1 and Compound 2 as the organometallic compounds represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both (e.g., simultaneously) be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0376] As used herein, the term “interlayer” refers to a single layer and / or multiple layers between the first electrode and the second electrode of a light-emitting device.
[0377] Figure 1 description
[0378] Figure 1 is a schematic cross-sectional view of a light-emitting device 10 according to one or more embodiments of the present disclosure. The light-emitting device 10 may include a first electrode 110, an interlayer 130, and a second electrode 150.
[0379] Hereinafter, with reference to Figure 1 describe the structure of the light-emitting device 10 according to one or more embodiments and a method of manufacturing the light-emitting device 10.
[0380] The first electrode 110
[0381] In Figure 1 , in one or more embodiments, a substrate may be additionally provided and located under the first electrode 110 and / or on the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be used. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or appropriate heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0382] The first electrode 110 can be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that facilitates hole injection can be used as the material for forming the first electrode 110.
[0383] The first electrode 110 can be a reflective electrode, a transmissive-reflective electrode, or a transmissive electrode. In one or more embodiments, to form the first electrode 110 as a transmissive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof can be used as the material for forming the first electrode 110. In one or more embodiments, to form the first electrode 110 as a transmissive-reflective 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.
[0384] The first electrode 110 can have a single-layer structure including a single layer (e.g., consisting of a single layer) or a multi-layer structure including multiple layers. For example, in some embodiments, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO.
[0385] Interlayer 130
[0386] The interlayer 130 can be located on the first electrode 110. The interlayer 130 can include an emission layer.
[0387] In one or more embodiments, the interlayer 130 can further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.
[0388] In one or more embodiments, in addition to one or more suitable organic materials, the interlayer 130 can further include a metal-containing compound (such as an organometallic compound, e.g., an organometallic compound represented by Formula 1) and / or an inorganic material (such as quantum dots), etc.
[0389] In one or more embodiments, the interlayer 130 can include i) two or more emission units stacked in sequence between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between the two or more emission units. When the interlayer 130 includes two or more emission units and a charge generation layer as described above, the light-emitting device 10 can be a tandem light-emitting device.
[0390] The hole transport region in the interlayer 130
[0391] The hole transport region may have i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material), ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes multiple different materials, or iii) a multi-layer structure including multiple layers that includes multiple different materials.
[0392] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0393] For example, in one or more embodiments, the hole transport region may have a multi-layer structure that includes a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where the constituent layers in each structure are stacked in the recited order sequentially from the first electrode 110.
[0394] In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0395] Formula 201
[0396]
[0397] Formula 202
[0398]
[0399] Wherein, in Formula 201 and Formula 202,
[0400] L 201 to L 204 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0401] L 205 may be *-O-*', *-S-*', *-N(Q 201 )-*', an unsubstituted or at least one R 10a substituted C1-C 20 alkylene, an unsubstituted or at least one R 10a substituted C2-C 20 alkenylene, an unsubstituted or at least one R 10a substituted C3-C 60A carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group,
[0402] xa1 to xa4 can each independently be an integer selected from 0 to 5,
[0403] xa5 can be an integer selected from 1 to 10,
[0404] R 201 to R 204 and Q 201 can each independently be an unsubstituted or at least one R- 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group,
[0405] R 201 and R 202 can optionally be connected to each other via a single bond, an unsubstituted or at least one R- 10a substituted C1-C5 alkylene group or an unsubstituted or at least one R- 10a substituted C2-C5 alkenylene group to form an unsubstituted or at least one R- 10a substituted C8-C 60 polycyclic group (e.g., carbazolyl, etc.) (e.g., see compound HT16, etc.),
[0406] R 203 and R 204 can optionally be connected to each other via a single bond, an unsubstituted or at least one R- 10a substituted C1-C5 alkylene group or an unsubstituted or at least one R- 10a substituted C2-C5 alkenylene group to form an unsubstituted or at least one R- 10a substituted C8-C 60 polycyclic group, and
[0407] na1 can be an integer selected from 1 to 4.
[0408] For example, in one or more embodiments, each of Formula 201 and Formula 202 can include at least one group selected from the groups represented by Formula CY201 to Formula CY217:
[0409]
[0410] wherein, in Formula CY201 to Formula CY217, R 10b and R 10c can each be the same as those described herein for R 10a and the ring CY201 to ring CY 204 may each independently be a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R as described herein 10a substituted.
[0411] According to one or more embodiments, in Formulae CY201 to CY217, ring CY 201 to ring CY 204 may each independently be phenyl, naphthyl, phenanthryl or anthryl.
[0412] According to one or more embodiments, each of Formulae 201 and 202 may include at least one group selected from the groups represented by Formulae CY201 to CY203.
[0413] According to one or more embodiments, Formula 201 may include at least one group selected from the groups represented by Formulae CY201 to CY203 and at least one group selected from the groups represented by Formulae CY204 to CY217.
[0414] According to one or more embodiments, in Formula 201, xa1 may be 1, R 201 may be a group represented by one selected from Formulae CY201 to CY203, xa2 may be 0, and R 202 may be a group represented by one selected from Formulae CY204 to CY207.
[0415] According to one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any group represented by Formulae CY201 to CY203.
[0416] According to one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any group represented by Formulae CY201 to CY203, and may include at least one group selected from the groups represented by Formulae CY204 to CY217.
[0417] According to one or more embodiments, each of Formulae 201 and 202 may not include (e.g., may exclude) any group represented by Formulae CY201 to CY217.
[0418] For example, in one or more embodiments, the hole transport region may include at least one selected from Compound HT1 to Compound HT46, 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), N,N'-bis(1-naphthyl)-N,N'-diphenyl-benzidine (NPB (NPD)), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:
[0419]
[0420]
[0421]
[0422]
[0423]
[0424] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about For example, about to about And the thickness of the hole transport layer may be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the above ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0425] The emission-assisting layer can increase luminous efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block electrons from the emission layer from leaking to the hole transport region. Materials that can be included in the hole transport region can be included in the emission-assisting layer and the electron blocking layer.
[0426] p-dopant
[0427] In one or more embodiments, in addition to one or more of the aforementioned materials, the hole transport region may further include a charge generation material for improved conductive properties. The charge generation material may be dispersed uniformly (e.g., substantially uniformly) or non-uniformly in the hole transport region (e.g., in the form of a single layer comprising (e.g., consisting of) the charge generation material).
[0428] The charge generating material may be, for example, a p-dopant.
[0429] For example, in one or more embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be -3.5 eV or less.
[0430] According to one or more embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0431] Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), and the like.
[0432] Non-limiting examples of the cyano group-containing compound may include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or a compound represented by Formula 221, etc.:
[0433]
[0434] Formula 221
[0435]
[0436] Where, in formula 221,
[0437] R 221 to R 223 may be each independently unsubstituted or substituted by at least one R 10a Substituted C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C1-C 60a heterocyclic group, and
[0438] selected from R 221 to R 223 at least one of which may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group each substituted by: cyano; -F; -Cl; -Br; -I; a C1-C 20 alkyl group substituted by cyano, -F, -Cl, -Br, -I or any combination thereof; or any combination thereof.
[0439] In a compound comprising element EL1 and element EL2, element EL1 may be a metal, a metalloid and / or a combination thereof (e.g., any suitable combination), and element EL2 may be a non-metal, a metalloid and / or a combination thereof (e.g., any suitable combination).
[0440] Non-limiting examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb) and / or cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and / or barium (Ba), etc.); 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), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au), etc.); post-transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn), etc.); and lanthanide metals (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.).
[0441] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb) and / or tellurium (Te), etc.
[0442] Non-limiting examples of non-metals may include oxygen (O) and / or halogens (e.g., F, Cl, Br and / or I, etc.), etc.
[0443] For example, a compound comprising element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides and / or metalloid iodides, etc.), metal tellurides or any combination thereof.
[0444] Non-limiting examples of metal oxides can 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 (e.g., MoO, Mo2O3, MoO2, MoO3, and / or Mo2O5, etc.), and / or rhenium oxides (e.g., ReO3, etc.), etc.
[0445] Non-limiting examples of metal halides can include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides, etc.
[0446] 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 / or CsI, etc.
[0447] 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 / or BaI2, etc.
[0448] 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(II) 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(I) halides (e.g., CuF, CuCl, CuBr, and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, and / or AgI, etc.), and / or gold halides (e.g., AuF, AuCl, AuBr, and / or AuI, etc.), etc.
[0449] 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 / or tin halides (e.g., SnI2, etc.), etc.
[0450] 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 / or SmI3, etc.
[0451] Non-limiting examples of metalloid halides may include antimony halides (e.g., SbCl5, etc.).
[0452] 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.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, and / or Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, and / or LuTe, etc.).
[0453] The emission layer in the interlayer 130
[0454] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to sub-pixels. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).
[0455] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0456] Based on 100 parts by weight of the host, the amount of the dopant in the emission layer may be about 0.01 part by weight to about 15 parts by weight.
[0457] In one or more embodiments, the emissive layer may include quantum dots.
[0458] In one or more embodiments, the emissive layer may include a delayed fluorescence material. The delayed fluorescence material may act as a host or a dopant in the emissive layer.
[0459] The thickness of the emissive layer may be about to about For example, about to about When the thickness of the emissive layer is within the above range, excellent or appropriate light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0460] Host
[0461] In one or more embodiments, the host may include a compound represented by Formula 301:
[0462] Formula 301
[0463] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21 ,
[0464] wherein, in Formula 301,
[0465] Ar 301 and L 301 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0466] xb11 may be 1, 2 or 3,
[0467] xb1 may be an integer selected from 0 to 5,
[0468] R 301 may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, an unsubstituted or at least one R 10a substituted C1-C 60 alkyl, an unsubstituted or at least one R 10a substituted C2-C 60 alkenyl, an unsubstituted or at least one R 10a substituted C2-C 60 alkynyl, an unsubstituted or at least one R 10a substituted C1-C 60 An alkoxy group, 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, -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 ),
[0469] xb21 can be an integer selected from 1 to 5, and
[0470] Q 301 to Q 303 can each be the same as described herein for Q1.
[0471] For example, in some embodiments, if (e.g., when) xb11 in Formula 301 is 2 or greater, then two or more Ars 301 can be connected to each other via a single bond.
[0472] In one or more embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0473] Formula 301-1
[0474]
[0475] Formula 301-2
[0476]
[0477] wherein, in Formula 301-1 and Formula 301-2,
[0478] Ring A 301 to Ring A 304 can each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0479] X 301 can be O, S, N[(L304 ) xb4 -R 304 , C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0480] xb22 and xb23 can each independently be 0, 1, or 2,
[0481] L 301 , xb1, and R 301 can each be the same as described herein,
[0482] L 302 to L 304 can each independently be the same as described herein for L 301 .
[0483] xb2 to xb4 can each independently be the same as described herein for xb1, and
[0484] R 302 to R 305 and R 311 to R 314 can each be the same as described herein for R 301 .
[0485] In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, in some embodiments, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0486] In one or more embodiments, the host may include at least one selected from compounds H1 to 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(9H-carbazol-9-yl)benzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:
[0487]
[0488]
[0489]
[0490]
[0491]
[0492]
[0493] Phosphorescent dopant
[0494] The phosphorescent dopant may include at least one transition metal as a central metal.
[0495] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0496] The phosphorescent dopant may be electrically neutral.
[0497] For example, in one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0498] Formula 401
[0499] M(L 401 ) xc1 (L 402 ) xc2
[0500] Formula 402
[0501]
[0502] Wherein, in Formula 401 and Formula 402,
[0503] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0504] L 401 may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein, if (e.g., when) xc1 is 2 or greater, then two or more L 401 may be the same as or different from each other,
[0505] L 402 may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, if (e.g., when) xc2 is 2 or greater, then two or more L 402 may be the same as or different from each other,
[0506] X 401 and X 402 may each independently be nitrogen or carbon,
[0507] Ring A 401 and Ring A402 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0508] 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(Q 411 )-*',
[0509] X 403 and X 404 may each independently be a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0510] Q 411 to Q 414 may each be the same as described herein for Q1,
[0511] R 401 and R 402 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an unsubstituted or at least one R 10a substituted C1-C 20 alkyl group, an unsubstituted or at least one R 10a substituted C1-C 20 alkoxy group, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or 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(Q401 ) or -P(=O)(Q 401 )(Q 402 ),
[0512] Q 401 to Q 403 may each be the same as described herein for Q1,
[0513] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0514] each of * and *' in Formula 402 indicates a binding site to M in Formula 401.
[0515] For example, in one or more embodiments, in Formula 402, i) X 401 may be nitrogen and X 402 may be carbon, or ii) each of X 401 and X 402 may be nitrogen.
[0516] In one or more embodiments, if (e.g., when) xc1 in Formula 401 is 2 or greater, then two or more of the two ring A 401 in L 401 may optionally be connected to each other via T 402 as a linking group, and / or the two ring A 402 may optionally be connected to each other via T 403 as a linking group (see Compound PD1 to Compound PD4 and Compound PD7). T 402 and T 403 may each be the same as described herein for T 401 described.
[0517] In Formula 401, L 402 may be an organic ligand. For example, L 402 may include a halogen, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isocyano group, a -CN group, a phosphorus-containing group (e.g., a phosphine group and / or a phosphite group, etc.) or any combination thereof.
[0518] In one or more embodiments, the phosphorescent dopant may include, for example, one or any combination selected from Compounds PD1 to PD39:
[0519]
[0520]
[0521]
[0522] Fluorescent dopant
[0523] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0524] For example, in one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:
[0525] Formula 501
[0526]
[0527] Wherein, in Formula 501,
[0528] Ar 501 , L 501 to L 503 , R 501 and R 502 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0529] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0530] xd4 may be 1, 2, 3, 4, 5 or 6.
[0531] For example, in one or more embodiments, Ar in Formula 501 501 may include a fused ring group in which three or more monocyclic groups are fused together (e.g., anthryl, 1,2-benzophenanthryl, and / or pyrenyl, etc.).
[0532] In one or more embodiments, xd4 in Formula 501 may be 2.
[0533] For example, in one or more embodiments, the fluorescent dopant may include at least one selected from Compound FD1 to Compound FD36, 4,4'-bis(2,2-diphenylethynyl)-1,1'-biphenyl (DPVBi), 4,4'-bis[4-(N,N-diphenylamino)styryl]biphenyl (DPAVBi), or any combination thereof:
[0534]
[0535]
[0536]
[0537] Thermally activated delayed fluorescence material
[0538] In one or more embodiments, the emission layer may include a delayed fluorescence material.
[0539] In the present disclosure, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0540] Depending on the type or species of other materials included in the emission layer, the delayed fluorescence material included in the emission layer may act as a host or a dopant.
[0541] According to one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material may be at least 0 eV but not greater than about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material is within the above range, upconversion from the triplet state to the singlet state of the delayed fluorescence material may occur effectively, and thus, the luminous efficiency of the light-emitting device 10 may be improved.
[0542] For example, in one or more embodiments, the delayed fluorescence material may include i) a material including at least one electron donor (e.g., a π - electron rich C3 - C 60 ring group, such as a carbazolyl group, etc.) and at least one electron acceptor (e.g., a sulfinyl group, a cyano group, and / or a π - electron deficient nitrogen - containing C1 - C 60 ring group, etc.), ii) a material including a C8 - C 60 polycyclic group in which two or more ring groups are fused while sharing a boron (B) atom, and / or iii) etc.
[0543] Non - limiting examples of the delayed fluorescence material may include at least one selected from Compound DF1 to Compound DF9:
[0544]
[0545] Quantum dots
[0546] In one or more embodiments, the emission layer may include quantum dots.
[0547] As used herein, the term "quantum dot" refers to a crystal of a semiconductor compound and may include any material capable of emitting light of one or more appropriate emission wavelengths according to the size of the crystal.
[0548] The diameter of the quantum dots can be, for example, from about 1 nm to about 10 nm. In the present disclosure, when the dots, multiple dots or dot particles are spherical, "diameter" indicates the particle size or average particle size, and when the particles are non-spherical, "diameter" indicates the major axis length or average major axis length. The diameter of the particles can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, the HORIBA, LA-950 laser particle size analyzer can be used. When measuring the size of the particles using a particle size analyzer, the average particle size is referred to as D 50 . D 50 refers to the average diameter of the particles whose cumulative volume corresponds to 50 vol% in the particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% starting from the smallest particles in the distribution curve accumulated in the order of the smallest particle size to the largest particle size when the total number of particles is 100%.
[0549] Quantum dots can be synthesized by wet chemical processes, metalorganic chemical vapor deposition (MOCVD) processes, molecular beam epitaxy (MBE) processes, or any process similar thereto.
[0550] The wet chemical process is a method that includes mixing precursor materials of quantum dots with an organic solvent and then growing quantum dot particle crystals. When the quantum dot particle crystals grow, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot particle crystals and controls the growth of the quantum dot particle crystals. Accordingly, the growth of the quantum dot particle crystals can be controlled or selected by a process that is less costly and easier than vapor deposition methods such as metalorganic chemical vapor deposition (MOCVD) and / or molecular beam epitaxy (MBE), etc.
[0551] Quantum dots can include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.
[0552] Non-limiting examples of II-VI group semiconductor compounds may include: binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and / or MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and / or MgZnS, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and / or HgZnSTe, etc.; or any combination thereof.
[0553] Non-limiting examples of III-V group semiconductor compounds may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and / or InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb, etc.; or any combination thereof. In one or more embodiments, the III-V group semiconductor compounds may further include a Group II element. Non-limiting examples of III-V group semiconductor compounds further including a Group II element may include InZnP, InGaZnP, and / or InAlZnP, etc.
[0554] Non-limiting examples of III-VI group semiconductor compounds may include: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and / or InTe, etc.; ternary compounds such as InGaS3 and / or InGaSe3, etc.; and / or any (e.g., any suitable) combination thereof.
[0555] Non-limiting examples of Group I-III-VI semiconductor compounds can include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, and / or AgAlO2, etc.; or any combination thereof.
[0556] Non-limiting examples of Group IV-VI semiconductor compounds can include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, and / or PbTe, etc.; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and / or SnPbTe, etc.; quaternary compounds such as SnPbSSe, SnPbSeTe, and / or SnPbSTe, etc.; and / or any combination (e.g., any suitable combination) thereof.
[0557] Group IV elements or compounds can include: single elements such as Si and / or Ge, etc.; binary compounds such as SiC and / or SiGe, etc.; and / or any combination (e.g., any suitable combination) thereof.
[0558] Each element included in a multi-element compound (such as a binary compound, a ternary compound, and a quaternary compound) can be present in the particles in a substantially uniform concentration or a non-uniform concentration.
[0559] In one or more embodiments, the quantum dots can have a single structure in which the concentration of each element included in the quantum dots is substantially uniform, or a core-shell dual structure. For example, the material included in the core and the material included in the shell can be different from each other.
[0560] The shell of the quantum dots can act as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties and / or act as a charging layer to impart electrophoretic properties to the quantum dots. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, in which the concentration of the element present in the shell decreases towards the center of the core.
[0561] Examples of the shell of the quantum dots can be oxides of metals, metalloids or non-metals, semiconductor compounds, and / or combinations thereof (e.g., any suitable combination). Non-limiting examples of oxides of metals, metalloids or non-metals can include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4, etc.; and / or combinations thereof (e.g., any suitable combination). Examples of semiconductor compounds can include: group II-VI semiconductor compounds as described herein; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; and / or combinations thereof (e.g., any suitable combination). For example, semiconductor compounds suitable as the shell can include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and / or combinations thereof (e.g., any suitable combination).
[0562] The full width at half maximum (FWHM) of the emission spectrum of the quantum dots can be about 45 nm or less, for example, about 40 nm or less, or about 30 nm or less, and within these ranges, the color purity or color reproducibility of the quantum dots can be increased. Additionally, since the light emitted by the quantum dots is emitted in all directions, the wide viewing angle can be improved.
[0563] In one or more embodiments, the quantum dots can be in the form of spherical nanoparticles, cone nanoparticles, multi-arm nanoparticles, cube nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates, etc.
[0564] Since the bandgap of the quantum dots can be adjusted by controlling the size of the quantum dots, light having one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Accordingly, by using quantum dots of different sizes, a light-emitting device that emits light having one or more suitable wavelengths can be realized. For example, the size of the quantum dots can be selected to ensure that the quantum dots emit red light, green light, and / or blue light. In one or more embodiments, quantum dots having suitable sizes can be configured to emit white light through a combination of light of one or more suitable colors.
[0565] The electron transport region in the interlayer 130
[0566] The electron transport region may have: i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material), ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a plurality of different materials, or iii) a multi-layer structure including a plurality of layers that includes a plurality of different materials.
[0567] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0568] For example, in one or more embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers in each structure are stacked in the recited order from the emission layer.
[0569] The electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one nitrogen-containing C1-C 60 π-deficient cyclic group.
[0570] For example, in one or more embodiments, the electron transport region may include a compound represented by Formula 601:
[0571] Formula 601
[0572] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 ,
[0573] wherein, in Formula 601,
[0574] Ar 601 and L 601 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0575] xe11 may be 1, 2, or 3,
[0576] xe1 may be 0, 1, 2, 3, 4, or 5,
[0577] R 601 may be unsubstituted or 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, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0578] Q 601 to Q 603 may each be the same as described herein for Q1,
[0579] xe21 may be 1, 2, 3, 4 or 5, and
[0580] selected from Ar 601 、L 601 and R 601 at least one of which may each independently be an unsubstituted or R 10a substituted π-deficient nitrogen-containing C1-C 60 cyclic group.
[0581] For example, in one or more embodiments, if (e.g., when) xe11 in Formula 601 is 2 or greater, then two or more Ar 601 may be linked together by a single bond.
[0582] In one or more embodiments, Ar in Formula 601 601 may be an unsubstituted or R 10a substituted anthryl group.
[0583] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
[0584] Formula 601-1
[0585]
[0586] wherein, in Formula 601-1,
[0587] X 614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X 616 may be N or C(R 616 ), and selected from X 614 to X 616At least one of them may be N,
[0588] L 611 to L 613 may each be the same as that described herein for L 601 described,
[0589] xe611 to xe613 may each be the same as that described herein for xe1,
[0590] R 611 to R 613 may each be the same as that described herein for R 601 described, and
[0591] R 614 to R 616 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group.
[0592] For example, in some embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.
[0593] In one or more embodiments, the electron transport region may include at least one selected from Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline) aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-ol) aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or any combination thereof:
[0594]
[0595]
[0596]
[0597] The thickness of the electron transport region may be about to about For example, about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be in the range of about to about For example, about to about and the thickness of the electron transport layer can be in the range of about to about For example, about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and / or the electron transport region is within the above ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0598] In one or more embodiments, in addition to one or more of the above materials, the electron transport region (e.g., the electron transport layer in the electron transport region) can further include a metal-containing material.
[0599] 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 Li ion, a Na ion, a K ion, an Rb ion, or a Cs ion, and the metal ion of the alkaline earth metal complex can be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0600] For example, in some embodiments, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1(Liq) or compound ET-D2:
[0601]
[0602] In one or more embodiments, the electron transport region can include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer can be in direct contact with the second electrode 150.
[0603] The electron injection layer may have: i) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes a single material (e.g., consisting of a single material), ii) a single-layer structure including a single layer (e.g., consisting of a single layer) that includes multiple different materials, or iii) a multi-layer structure including multiple layers that includes multiple different materials.
[0604] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0605] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0606] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may respectively include oxides, halides (e.g., fluorides, chlorides, bromides, and / or iodides, etc.) or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0607] The alkali metal compound may include alkali metal oxides such as Li2O, Cs2O, and / or K2O, etc.; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI, etc.; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides 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), etc. The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal compound may include lanthanide metal tellurides. Non-limiting examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and / or Lu2Te3, etc.
[0608] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may respectively include i) one of the metal ions of alkali metals, one of the metal ions of alkaline earth metals, and one of the metal ions of rare earth metals, and ii) ligands bonded to the respective metal ions, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0609] In one or more embodiments, the electron injection layer may include (e.g., consist of) the alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In one or more embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0610] According to one or more embodiments, the electron injection layer may 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, alkaline earth metal, rare earth metal, or any combination thereof. For example, in one or more embodiments, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, and / or a LiF:Yb co-deposited layer, etc.
[0611] When the electron injection layer further includes an organic material, the alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in a matrix including the organic material.
[0612] The thickness of the electron injection layer may be about to about For example, about to about When the thickness of the electron injection layer is within the range as described above, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0613] The second electrode 150
[0614] The second electrode 150 may be located on the interlayer 130. The second electrode 150 may be a cathode serving as an electron injection electrode, and as a material for forming the second electrode 150, a metal, alloy, conductive compound, or any combination thereof each having a low work function may be used.
[0615] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode.
[0616] The second electrode 150 may have a single-layer structure including a single layer or a multi-layer structure including multiple layers.
[0617] Capping layer
[0618] The first capping layer may be located outside the first electrode 110 (e.g., on the first electrode 110) and / or the second capping layer may be located outside the second electrode 150 (e.g., on the second electrode 150). For example, in one or more embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in the described 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 described 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 described order.
[0619] In one or more embodiments, the light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the first electrode 110 and the first capping layer, which are a transmissive-reflective electrode or a transmissive electrode. In one or more embodiments, the light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted toward the outside through the second electrode 150 and the second capping layer, which are a transmissive-reflective electrode or a transmissive electrode.
[0620] The first capping layer and the second capping layer may increase the external light-emitting efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, so that the light-emitting efficiency of the light-emitting device 10 can be increased.
[0621] Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or greater (e.g., at 589 nm).
[0622] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.
[0623] At least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amino group-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amino group-containing compound may each optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include an amino group-containing compound.
[0624] For example, in one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0625] According to one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include at least one selected from Compound HT28 to Compound HT33, at least one selected from Compound CP1 to Compound CP6, β-NPB, or any combination thereof:
[0626]
[0627] Film
[0628] The organometallic compound represented by Formula 1 may be included in one or more suitable films. Accordingly, one or more aspects of embodiments of the present disclosure relate to a film including the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or a light control element) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, and / or a quantum dot-containing layer, etc.), a light-blocking member (e.g., a light reflection layer and / or a light absorption layer, etc.), and / or a protection member (e.g., an insulating layer and / or a dielectric layer, etc.).
[0629] Electronic device
[0630] The light-emitting device may be included in one or more suitable electronic devices. For example, in one or more embodiments, the electronic device including the light-emitting device may be a light-emitting device and / or an authentication device, etc.
[0631] In one or more embodiments, in addition to the light-emitting device, an electronic device (e.g., a lighting device) may 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 may be disposed in at least one traveling direction of the light emitted from the light-emitting device. For example, in some embodiments, the light emitted from the light-emitting device may be blue light or white light (e.g., combined white light). A detailed description of the light-emitting device is provided above. According to one or more embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.
[0632] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.
[0633] The pixel defining film may be disposed between the plurality of sub-pixel regions to define each of the plurality of sub-pixel regions.
[0634] The color filter may further include a plurality of color filter regions and a light-shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern disposed between the plurality of color conversion regions.
[0635] The plurality of color filter regions (or the plurality of color conversion regions) may include: a first region configured to emit first color light; a second region configured to emit second color light; and / or a third region configured to emit third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. For example, in one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, in one or more embodiments, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. For example, in some embodiments, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) quantum dots. A detailed description of the quantum dots is provided herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0636] For example, in one or more embodiments, the light-emitting device may emit first light, the first region may absorb the first light to emit first first-color light, the second region may absorb the first light to emit second first-color light, and the third region may absorb the first light to emit third first-color light. In this case, the first first-color light, the second first-color light, and the third first-color light may have different maximum emission wavelengths. For example, in one or more embodiments, the first light may be blue light, the first first-color light may be red light, the second first-color light may be green light, and the third first-color light may be blue light.
[0637] In one or more embodiments, in addition to the light-emitting device as described above, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, where one selected from the source electrode and the drain electrode may be electrically connected to the first electrode or the second electrode of the light-emitting device.
[0638] The thin-film transistor may further include a gate electrode and / or a gate insulating film, etc.
[0639] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.
[0640] In one or more embodiments, the electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and / or the color conversion layer and the light-emitting device. The sealing portion may allow light to be extracted from the light-emitting device to the outside, and at the same time (e.g., synchronously) prevent or reduce the penetration of ambient air and moisture into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including one or more layers of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.
[0641] In one or more embodiments, depending on the use of the electronic device, in addition to the color filter and / or the color conversion layer, various functional layers may be additionally located on the sealing portion. Non-limiting examples of the functional layer may include a touchscreen layer and / or a polarization layer, etc. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer.
[0642] In addition to the light-emitting device as described above, the authentication device may further include a biometric information collector. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., a fingertip and / or a pupil, etc.).
[0643] The electronic device can be applied to one or more displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical tools (e.g., electronic thermometers, sphygmomanometers, glucometers, pulse measurement devices, pulse wave measurement devices, electrocardiogram monitors, ultrasonic diagnostic devices, and / or endoscope monitors, etc.), fish finders, one or more appropriate measurement tools, meters (e.g., meters for vehicles, aircraft, and ships), and / or projectors, etc.
[0644] Figure 2 and Figure 3 description
[0645] Figure 2 FIG. is a cross-sectional view showing a light-emitting device according to one or more embodiments of the present disclosure.
[0646] Figure 2 The light-emitting device may include a substrate 100, a thin-film transistor (TFT), a light-emitting device, and a sealing portion 300 for sealing the light-emitting device.
[0647] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0648] The TFT may be on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0649] The active layer 220 may include an inorganic semiconductor (such as silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0650] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.
[0651] An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate them from each other.
[0652] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be respectively located at the exposed portions in contact with the source region and the drain region of the active layer 220.
[0653] The TFT can be electrically connected to the light-emitting device to drive the light-emitting device and can be covered and protected by the passivation layer 280. The passivation layer 280 can include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device can be provided on the passivation layer 280. The light-emitting device can include a first electrode 110, an interlayer 130, and a second electrode 150.
[0654] The first electrode 110 can be on the passivation layer 280. The passivation layer 280 can be located at a specific portion exposing the drain electrode 270 and does not completely cover the drain electrode 270, and the first electrode 110 can be located at the exposed portion connected to the drain electrode 270.
[0655] The pixel defining film 290 including an insulating material can be on the first electrode 110. The pixel defining film 290 can expose a specific region of the first electrode 110, and the interlayer 130 can be formed in the exposed region of the first electrode 110. The pixel defining film 290 can be a polyimide-based organic film or a polyacrylic-based organic film. In one or more embodiments, at least some layers of the interlayer 130 can extend beyond the upper portion of the pixel defining film 290 and be placed in the form of a common layer.
[0656] The second electrode 150 can be on the interlayer 130, and a capping layer 170 can be additionally formed on the second electrode 150. The capping layer 170 can be formed to cover the second electrode 150.
[0657] The sealing portion 300 can be on the capping layer 170. The sealing portion 300 can be located on the light-emitting device to protect the light-emitting device from moisture and / or oxygen. The sealing portion 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, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; and / or a (e.g., any suitable) combination of an inorganic film and an organic film.
[0658] Figure 3 It is a cross-sectional view showing a light-emitting device according to one or more embodiments of the present disclosure.
[0659] Figure 3 The light-emitting device of Figure 2The light-emitting devices are substantially the same, except that the light-shielding pattern 500 and the functional region 400 are additionally located on the sealing portion 300. The functional region 400 may be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. According to one or more embodiments, Figure 3 The light-emitting device included in the light-emitting device may be a series light-emitting device.
[0660] Figure 4 description
[0661] Figure 4 FIG. 10 is a schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments of the present disclosure. As a device for displaying moving images or still images, the electronic device 1 may be a portable electronic device (such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile PC (UMPC)), and one or more suitable products (such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IoT) device). The electronic device 1 may be such a product or a part thereof. In one or more embodiments, the electronic device 1 may be a wearable device (such as a smartwatch, a watch phone, a glasses-type or -kind display, or a head-mounted display (HMD)) or a part of a wearable device. However, the embodiments of the present disclosure are not limited thereto. For example, in one or more embodiments, the electronic device 1 may include a vehicle dashboard, a vehicle center console, a center information display disposed on the vehicle dashboard, an in-vehicle mirror display replacing a vehicle side mirror, an entertainment display for a vehicle rear seat, a display disposed on the backrest of its front seat, a head-up display (HUD) mounted in front of the vehicle or projected onto a front window glass, and / or a computer-generated holographic augmented reality head-up display (CGHAR HUD). For ease of explanation, Figure 4 FIG. 11 illustrates an embodiment in which the electronic device 1 is a smartphone.
[0662] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device of the electronic device 1 may implement an image through a plurality of pixel arrays two-dimensionally arranged in the display area DA.
[0663] The non-display area NDA is an area where no image is displayed and may be completely around (e.g., surrounding) the display area DA. In the non-display area NDA, a driver for supplying an electrical signal or power to a display element disposed in the display area DA may be disposed. In the non-display area NDA, pads may be disposed, and the pads may be electrically connected to electronic components or a printed circuit board.
[0664] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction (e.g., the width) may be different from each other. For example, in one or more embodiments, as Figure 4 shown, the length in the x-axis direction may be less than the length in the y-axis direction (e.g., the width). In one or more embodiments, the length in the x-axis direction may be substantially the same as the length in the y-axis direction (e.g., the width). In one or more embodiments, the length in the x-axis direction may be greater than the length in the y-axis direction (e.g., the width).
[0665] Figure 5 and Figures 6A to 6C the description of
[0666] Figure 5 is a schematic diagram of the exterior of the vehicle 1000 as an electronic device including a light-emitting device according to one or more embodiments. Figures 6A to 6C Each is a schematic diagram of the interior of the vehicle 1000 according to one or more embodiments.
[0667] See Figure 5 、 Figure 6A 、 Figure 6B and Figure 6C , the vehicle 1000 may refer to one or more suitable devices for moving an object to be transported (such as a person, an object or an animal) from a starting point to a destination point. The vehicle 1000 may include vehicles traveling on roads or tracks, ships moving on the ocean or rivers, and / or airplanes flying in the air by utilizing the action of air, etc.
[0668] In one or more embodiments, the vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a specific direction according to the rotation of at least one of its wheels. For example, the vehicle 1000 may include three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, prime mover devices, bicycles, or trains traveling on tracks.
[0669] The vehicle 1000 may include a body having an interior and an exterior, and a chassis as other parts outside the body on which mechanical equipment required for driving is installed. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between the doors. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front and rear wheels, and / or left and right wheels, etc.
[0670] The vehicle 1000 may include side window glass 1100, front window glass 1200, side mirrors 1300, a dashboard 1400, a center console 1500, a passenger seat dashboard 1600, and a display device 2.
[0671] The side window glass 1100 and the front window glass 1200 may be divided by a pillar disposed between the side window glass 1100 and the front window glass 1200.
[0672] The side window glass 1100 may be installed on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be installed on the door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In one or more embodiments, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one or more embodiments, the first side window glass 1110 may be disposed adjacent to the instrument panel 1400. The second side window glass 1120 may be disposed adjacent to the passenger seat instrument panel 1600.
[0673] In one or more embodiments, the side window glasses 1100 may be spaced apart and / or separated (e.g., spaced or divided) from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart and / or separated from each other in the x-axis direction or the -x-axis direction (e.g., spaced or divided). For example, an imaginary straight line L connecting the side window glasses 1100 may extend in the x-axis direction or the -x-axis direction. For example, an imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-axis direction or the -x-axis direction.
[0674] The front window glass 1200 may be installed in the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0675] The side mirror 1300 may provide a rear view of the vehicle 1000. The side mirror 1300 may be installed on the exterior of the vehicle body. In one or more embodiments, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be disposed outside the first side window glass 1110. Another one of the plurality of side mirrors 1300 may be disposed outside the second side window glass 1120.
[0676] The instrument panel 1400 may be disposed in front of the steering wheel. The instrument panel 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a tachograph, an automatic shift lever indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0677] The center console 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and / or a seat heater are disposed. The center console 1500 may be disposed on one side of the instrument panel 1400.
[0678] The passenger seat dashboard 1600 may be separated from and / or apart from (e.g., spaced or divided) the instrument panel 1400, and the center console 1500 is disposed between the passenger seat dashboard 1600 and the instrument panel 1400. In one or more embodiments, the instrument panel 1400 may be arranged corresponding to the driver's seat, and the passenger seat dashboard 1600 may be arranged corresponding to the passenger seat. In one or more embodiments, the instrument panel 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.
[0679] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be disposed inside the vehicle 1000. In one or more embodiments, the display device 2 may be disposed between the side window glasses 1100 facing each other. The display device 2 may be disposed on at least one of the instrument panel 1400, the center console 1500, and the passenger seat dashboard 1600.
[0680] The display device 2 may include an organic light emitting display, an inorganic electroluminescent (EL) display, and / or a quantum dot display, etc. Hereinafter, as the display device 2 according to one or more embodiments, an organic light emitting display including a light emitting device according to the present disclosure will be described as an example, but one or more appropriate types (kinds) of display devices as described above may be used in the embodiments.
[0681] See Figure 6A , in one or more embodiments, the display device 2 may be disposed on the center console 1500. In one or more embodiments, the display device 2 may display navigation information. In one or more embodiments, the display device 2 may display audio, video, or information about vehicle settings.
[0682] See Figure 6B , in one or more embodiments, the display device 2 may be disposed on the instrument panel 1400. In these embodiments, the instrument panel 1400 may display driving information, etc. through the display device 2. For example, the instrument panel 1400 may be digitized. The instrument panel 1400 may digitally display vehicle information and driving information as images. For example, the pointer and gauge of the tachometer and one or more appropriate warning light icons may be displayed by digital signals.
[0683] See Figure 6C, in one or more embodiments, the display device 2 may be disposed on the passenger seat dashboard 1600. The display device 2 may be embedded in or disposed on the passenger seat dashboard 1600. In one or more embodiments, the display device 2 disposed on the passenger seat dashboard 1600 may display an image related to the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500. In one or more embodiments, the display device 2 disposed on the passenger seat dashboard 1600 may display information different from the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500.
[0684] Manufacturing method
[0685] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region may each be formed in a certain region by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0686] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are each formed by vacuum deposition, depending on the material to be included in the layer to be formed and the structure of the layer to be formed, the deposition temperature may be in the range of about 100 °C to about 500 °C, and the vacuum degree may be in the range of about -8 Torr to about -3 Torr, and the deposition may be carried out at a deposition rate in the range of about seconds to about seconds.
[0687] Definition of terms
[0688] As used herein, the term "C3-C 60 carbocyclic group" refers to a cyclic group that includes only carbon (e.g., composed of carbon) as the ring-forming atom and has 3 to 60 carbon atoms. For example, C3-C 50 carbocyclic group, C3-C 40 carbocyclic group, C3-C 30 carbocyclic group, C3-C 20 carbocyclic group, or C3-C 10 carbocyclic group. And as used herein, the term "C1-C 60 heterocyclic group" refers to a cyclic group that has 1 to 60 carbon atoms and further includes a heteroatom as the ring-forming atom in addition to carbon atoms. For example, C1-C 50 heterocyclic group, C1-C 40 heterocyclic group, C1-C 30 heterocyclic group, C1-C 20 heterocyclic group, or C1-C 10 heterocyclic group. C3-C60 A carbocyclic group and C1-C 60 The heterocyclic group may each be a monocyclic group including one (e.g., exactly one) ring (e.g., consisting of one ring) or a polycyclic group in which two or more rings are fused to each other. For example, C1-C 60 The number of ring-forming atoms of the heterocyclic group may be from 3 to 61.
[0689] As used herein, the term "cyclic group" may include (e.g., simultaneously) C3-C 60 A carbocyclic group and C1-C 60 Both heterocyclic groups.
[0690] As used herein, the term "π-electron-rich C3-C 60 cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including *-N=*' as a ring-forming moiety, and as used herein, the term "π-electron-deficient nitrogen-containing C1-C 60 cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming moiety.
[0691] For example,
[0692] C3-C 60 The carbocyclic group may be i) group T1 or ii) a fused-ring group in which two or more groups T1 are fused to each other (e.g., cyclopentadienyl, adamantyl, norbornyl, phenyl, pentaphenylenyl, naphthyl, azulyl, indacenyl, acenaphthyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentaphenyl, heptaphenylenyl, tetracenyl, picenyl, hexaphenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthrenyl or indenanthryl),
[0693] C1-C 60The heterocyclic group may be i) group T2, ii) a fused ring group in which two or more groups T2 are fused to each other, or iii) a fused ring group in which at least one group T2 and at least one group T1 are fused to each other (for example, pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzoisoindolyl, naphthobenzoisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indeno[1,2-b]carbazolyl, indolo[3,2-b]carbazolyl, benzofuro[3,2-b]carbazolyl, benzothieno[3,2-b]carbazolyl, benzosilolo[3,2-b]carbazolyl, benzindolo[3,2-b]carbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofuro[3,2-b]dibenzofuryl, benzofuro[3,2-b]dibenzothienyl, benzothieno[3,2-b]dibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzothienyl and / or azadibenzofuryl, etc.),
[0694] π - electron - rich C3 - C 60 The cyclic group may be i) group T1, ii) a fused ring group in which two or more groups T1 are fused to each other, iii) group T3, iv) a fused ring group in which two or more groups T3 are fused to each other, or v) a fused ring group in which at least one group T3 and at least one group T1 are fused to each other (for example, C3 - C 60 carbocyclic group, 1H - pyrrolyl, silolyl, borolyl, 2H - pyrrolyl, 3H - pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzoisoindolyl, naphthobenzoisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, indeno[1,2 - b]carbazolyl, indolo[3,2 - b]carbazolyl, benzofuro[3,2 - b]carbazolyl, benzothieno[3,2 - b]carbazolyl, benzosilolo[3,2 - b]carbazolyl, benzindolo[3,2 - b]carbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofuro[3,2 - b]dibenzofuryl, benzofuro[3,2 - b]dibenzothienyl and / or benzothieno[3,2 - b]dibenzothienyl, etc.),
[0695] π - electron - deficient nitrogen - containing C1 - C 60The cyclic group can be i) group T4, ii) a fused ring group in which two or more groups T4 are fused to each other, iii) a fused ring group in which at least one group T4 and at least one group T1 are fused to each other, iv) a fused ring group in which at least one group T4 and at least one group T3 are fused to each other, or v) a fused ring group in which at least one group T4, at least one group T1 and at least one group T3 are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorene, azadibenzosilolyl, azadibenzothiophenyl and / or azadibenzofuranyl, etc.),
[0696] Group T1 can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptanyl), norbornenyl, bicyclo[1.1.1]pentanyl, bicyclo[2.1.1]hexanyl, bicyclo[2.2.2]octanyl or phenyl,
[0697] Group T2 can be furyl, thienyl, 1H - pyrrolyl, silolyl, borolyl, 2H - pyrrolyl, 3H - pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridyl, dihydropyridyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,
[0698] Group T3 can be furyl, thienyl, 1H - pyrrolyl, silolyl or borolyl, and
[0699] Group T4 can be 2H - pyrrolyl, 3H - pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.
[0700] As used herein, the terms "cyclic group", "C3-C 60 carbocyclic group", "C1-C 60 heterocyclic group", "π-electron rich C3-C 60 cyclic group" or "nitrogen-containing π-electron poor C1-C 60 cyclic group" may refer to a monovalent or polyvalent group (e.g., divalent, trivalent, and / or tetravalent groups, etc.) that is fused (e.g., joined together) to a cyclic group according to the structure of a formula in which the corresponding term is used. For example, "phenyl" may be benzyl, phenyl, and / or phenylene, etc., and those of ordinary skill in the art can readily understand these groups according to the structure of a formula that includes "phenyl".
[0701] Monovalent C3-C 60 carbocyclic groups and monovalent C1-C 60 heterocyclic groups may include, without limitation, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups. Divalent C3-C 60 carbocyclic groups and divalent C1-C 60 heterocyclic groups may include, without limitation, C3-C 10 cycloalkylidene, C1-C 10 heterocycloalkylidene, C3-C 10 cycloalkenylidene, C1-C 10 heterocycloalkenylidene, C6-C 60 arylidene, C1-C 60 heteroarylidene, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups.
[0702] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched-chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, e.g., C1-C 50 alkyl, C1-C 30 alkyl, C1-C 20 alkyl, or C1-C 10alkyl, and non-limiting examples thereof may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, and / or tert-decyl, etc. As used herein, the term "C1-C 60 alkylene" refers to a divalent group having substantially the same structure as C1-C 60 alkyl.
[0703] As used herein, the term "C2-C 60 alkenyl" refers to a monovalent hydrocarbon group having one or more carbon-carbon double bonds in the middle or at the end of C2-C 60 alkyl, for example, C2-C 30 alkenyl, C2-C 20 alkenyl or C2-C 10 alkenyl, and non-limiting examples thereof may include vinyl, propenyl, and / or butenyl, etc. As used herein, the term "C2-C 60 alkenylene" refers to a divalent group having substantially the same structure as C2-C 60 alkenyl.
[0704] As used herein, the term "C2-C 60 alkynyl" refers to a monovalent hydrocarbon group having one or more carbon-carbon triple bonds in the middle or at the end of C2-C 60 alkyl, for example, C2-C 30 alkynyl, C2-C 20 alkynyl or C2-C 10 alkynyl, and non-limiting examples thereof may include ethynyl and / or propynyl, etc. As used herein, the term "C2-C 60 alkynylene" refers to a divalent group having substantially the same structure as C2-C 60 alkynyl.
[0705] As used herein, the term "C1-C 60 alkoxy" refers to a monovalent group represented by -OA 101 (where A 101 is C1-C 60 alkyl), for example, C1-C 30 alkoxy, C1-C 20 alkoxy or C1-C 10 alkoxy, and non-limiting examples thereof include methoxy, ethoxy, and / or isopropoxy, etc.
[0706] As used herein, the term "C3-C10 "Cycloalkyl" means a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and / or bicyclo[2.2.2]octyl, etc. As used herein, the term "C3-C 10 "Subcycloalkyl" means a divalent group having substantially the same structure as C3-C 10 cycloalkyl.
[0707] As used herein, the term "C1-C 10 "Heterocycloalkyl" means a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and non-limiting examples thereof may include 1,2,3,4-oxadiazolyl, tetrahydrofuryl, and / or tetrahydrothienyl, etc. As used herein, the term "C1-C 10 "Subheterocycloalkyl" means a divalent group having substantially the same structure as C1-C 10 heterocycloalkyl.
[0708] As used herein, the term "C3-C 10 "Cycloalkenyl" means a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and no aromaticity, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl, and / or cycloheptenyl, etc. As used herein, the term "C3-C 10 "Subcycloalkenyl" means a divalent group having substantially the same structure as C3-C 10 cycloalkenyl.
[0709] As used herein, the term "C1-C 10 "Heterocycloalkenyl" means a monovalent cyclic group having 1 to 10 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and having at least one double bond in its ring. Non-limiting examples of C1-C 10 heterocycloalkenyl may include 4,5-dihydro-1,2,3,4-oxadiazolyl, 2,3-dihydrofuryl, and / or 2,3-dihydrothienyl, etc. As used herein, the term "C1-C 10 "Subheterocycloalkenyl" means a divalent group having substantially the same structure as C1-C 10 heterocycloalkenyl.
[0710] As used herein, the term "C6-C 60 "Aryl" means a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, C6-C 50 aryl, C6-C40 Aryl, C6-C 30 Aryl, C6-C 20 Aryl or C6-C 15 Aryl, and as used herein the term "C6-C 60 arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. C6-C 60 Non-limiting examples of aryl may include phenyl, pentaphenylenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, perylenyl, pentaphenyl, heptaphenylenyl, tetracenyl, picenyl, hexaphenyl, pentaphenyl, rubicenyl, coronenyl, and / or ovalenyl, etc. When C6-C 60 aryl and C6-C 60 arylene each include two or more rings, the two or more rings may be fused to each other.
[0711] As used herein the term "C1-C 60 heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, e.g., C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl or C1-C 10 heteroaryl. As used herein the term "C1-C 60 heteroarylene" refers to a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. C1-C 60 Non-limiting examples of heteroaryl may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and / or naphthyridinyl, etc. When C1-C 60 heteroaryl and C1-C 60 heteroarylene each include two or more rings, the two or more rings may be fused to each other.
[0712] As used herein the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, with only carbon atoms (e.g., 8 to 60 carbon atoms) as ring-forming atoms and having no aromaticity in its molecular structure when considered as a whole, e.g., C8-C 60 monovalent non-aromatic fused polycyclic group, C8-C 50Monovalent non-aromatic fused polycyclic group, C8-C 40 Monovalent non-aromatic fused polycyclic group, C8-C 30 Monovalent non-aromatic fused polycyclic group or C8-C 20 Monovalent non-aromatic fused polycyclic group. Non-limiting examples of the monovalent non-aromatic fused polycyclic group may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenoanthracenyl, and / or indenoanthracenyl, etc. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused polycyclic group.
[0713] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group having two or more rings fused to each other, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity in its molecular structure when considered as a whole. For example, C1-C 60 Monovalent non-aromatic fused heteropolycyclic group, C1-C 50 Monovalent non-aromatic fused heteropolycyclic group, C1-C 40 Monovalent non-aromatic fused heteropolycyclic group, C1-C 30 Monovalent non-aromatic fused heteropolycyclic group or C1-C 20 Monovalent non-aromatic fused heteropolycyclic group. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group may include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzothienyl, benzofuryl, carbazolyl, dibenzosilolyl, dibenzothienyl, dibenzofuryl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzothienyl, azadibenzofuryl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthothienyl, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzothienyl, and / or benzothienodibenzothienyl, etc. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having substantially the same structure as the monovalent non-aromatic fused heteropolycyclic group.
[0714] As used herein, the term "C6-C 60 Aryloxy" refers to -OA 102 (where A102 For C6-C 60 aryl), for example, C6-C 50 aryloxy, C6-C 40 aryloxy, C6-C 30 aryloxy, C6-C 20 aryloxy or C6-C 15 aryloxy, and as used herein the term "C6-C 60 arylthio" means -SA 103 (where A 103 is C6-C 60 aryl), for example, C6-C 50 arylthio, C6-C 40 arylthio, C6-C 30 arylthio, C6-C 20 arylthio or C6-C 15 arylthio.
[0715] As used herein the term "C7-C 60 aralkyl" means -A 104 A 105 (where A 104 is C1-C 54 alkylene, and A 105 is C6-C 59 aryl), for example, C7-C 50 aralkyl, C7-C 40 aralkyl, C7-C 30 aralkyl, C7-C 20 aralkyl or C7-C 15 aralkyl, and as used herein the term "C2-C 60 heteroaralkyl" means -A 106 A 107 (where A 106 is C1-C 59 alkylene, and A 107 is C1-C 59 heteroaryl), for example, C2-C 50 heteroaralkyl, C2-C 40 heteroaralkyl, C2-C 30 heteroaralkyl, C2-C 20 heteroaralkyl or C2-C 15 heteroaralkyl.
[0716] As used herein the terms "R 10a " and "R 10b " may be:
[0717] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0718] Each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(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;
[0719] Each unsubstituted or substituted by the following C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q21 )(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
[0720] -Si(Q 31 )(Q 32 )(Q 33 )、 -Ge(Q 31 )(Q 32 )(Q 33 )、 -N(Q 31 )(Q 32 )、 -B(Q 31 )(Q 32 )、 -P(Q 31 )(Q 32 )、 -O(Q 31 )、 -S(Q 31 )、 -C(=O)(Q 31 )、 -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 )。
[0721] As used herein, Q1 to Q3, Q 11 to Q 13 、 Q 21 to Q 23 and Q 31 to Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; or C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof, unsubstituted or substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
[0722] As used herein, the term "heteroatom" refers to any atom other than a carbon atom and a hydrogen atom. Non-limiting examples of such heteroatoms can include B, O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0723] As used herein, "Ph" refers to a phenyl group, "Me" refers to a methyl group, "Et" refers to an ethyl group, "tert-Bu" or "Bu t " refers to a tert-butyl group, and "OMe" as used herein refers to a methoxy group.
[0724] As used herein, the term "biphenyl" refers to "a phenyl group substituted with a phenyl group". "Biphenyl" can be a substituted phenyl group having a C6-C 60 aryl group as a substituent.
[0725] As used herein, the term "terphenyl" refers to "a phenyl group substituted with a biphenyl group". "Terphenyl" can be a substituted phenyl group having a C6-C 60 aryl group substituted with a C6-C 60 aryl group as a substituent.
[0726] Unless otherwise defined, *、*' and *" as used herein each refer to the binding site to an adjacent atom in the corresponding formula or moiety.
[0727] Hereinafter, compounds according to one or more embodiments and light-emitting devices according to one or more embodiments will be described in more detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in describing the synthesis examples means using substantially the same molar equivalent of B instead of A.
[0728] Examples
[0729] Synthesis Example 1: Synthesis of Compound 1
[0730]
[0731] Synthesis of Intermediate Compound 1-A
[0732] 2-Bromo-4-(tert-butyl)pyridine (1.0 eq), 2-methoxy-9H-carbazole (1.2 eq), copper(I) iodide (0.01 eq), picolinic acid (0.02 eq), and cesium carbonate (2.0 eq) were dissolved in dimethyl sulfoxide (DMSO) (1.0 M) and stirred at 100 °C for 12 h. The reaction mixture was cooled to room temperature and the organic layer was obtained by performing a three-time extraction process using dichloromethane and water. The obtained organic layer was dried using magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound 1-A (yield 90%).
[0733] Synthesis of intermediate compound 1-B
[0734] n-Butyllithium (nBuLi) (1 M in hexanes, 4.0 eq) was slowly added to a mixture of intermediate compound 1-A (1.0 eq) and tetramethylethylenediamine (4.0 eq), and the mixture was stirred at 60 °C for 6 h. The reaction mixture was dissolved in tetrahydrofuran (0.22 M) and stirred at -78 °C. 2,2-Dichloropropane (Me2CCl2) (1.0 eq) was added thereto, and the reaction mixture was stirred at room temperature for 17 h. The reaction mixture was diluted with an excess of ice water, and the organic layer was obtained by performing a three-time extraction process using ethyl acetate. The obtained organic layer was dried using magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound 1-B (yield 32%).
[0735] Synthesis of intermediate compound 1-C
[0736] Intermediate compound 1-B (1.0 eq) was dissolved in dichloromethane (0.1 M), and boron tribromide (2.0 eq) was slowly added thereto while stirring at 0 °C, and then the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with distilled water and neutralized with 30 wt% aqueous sodium hydroxide solution. The organic layer was obtained by performing a three-time extraction process using dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and then concentrated to synthesize intermediate compound 1-C (yield 90%).
[0737] Synthesis of intermediate compound 1-D
[0738] The intermediate compound 1-C (1.0 eq), 1,3-dibromobenzene (2.0 eq), copper(I) iodide (0.01 eq), K2CO3 (2.0 eq) and L-proline (0.02 eq) were dissolved in DMSO (0.1 M) and stirred at 130 °C for 24 h. The reaction mixture was cooled to room temperature and subjected to a three-time extraction process using dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound 1-D (yield 85%).
[0739] Synthesis of intermediate compound 1-F
[0740] The intermediate compound 1-D (1.0 eq), intermediate compound 1-E (1.0 eq), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (5.0 mol%), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos) (0.1 eq) and sodium tert-butoxide (2.0 eq) were dissolved in toluene (0.5 M) and stirred at 120 °C for 4 h. The reaction mixture was cooled to room temperature and subjected to a three-time extraction process using dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound 1-F (yield 81%).
[0741] Synthesis of intermediate compound 1-G
[0742] The intermediate compound 1-F (1.0 eq), triethyl orthoformate (50 eq) and hydrochloric acid (aq. 12 M, 3.0 eq) were stirred at 80 °C for 12 h. The reaction mixture was cooled to room temperature and subjected to a three-time extraction process using dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize the intermediate compound 1-G (yield 73%).
[0743] Synthesis of compound 1
[0744] The intermediate compound 1-G (1.0 eq), dichloro(1,5-cyclooctadiene)platinum (Pt(COD)Cl2) (1.2 eq) and sodium acetate (2.0 eq) were dissolved in 1,4-dioxane (0.5 M) and stirred at 120 °C for 48 h. The reaction mixture was cooled to room temperature and subjected to a three-time extraction process using dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize compound 1 (yield 36%).
[0745] Synthesis Example 2: Synthesis of compound 61
[0746]
[0747] Synthesis of Intermediate Compound 61-B
[0748] Intermediate Compound 61-B was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-B (yield 56%), except that dimethyldichlorosilane (Me2SiCl2) (1.0 eq) was used instead of 2,2-dichloropropane (1.0 eq).
[0749] Synthesis of Intermediate Compound 61-C
[0750] Intermediate Compound 61-C was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-C (yield 88%), except that Intermediate Compound 61-B (1.0 eq) was used instead of Intermediate Compound 1-B (1.0 eq).
[0751] Synthesis of Intermediate Compound 61-D
[0752] Intermediate Compound 61-D was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-D (yield 82%), except that Intermediate Compound 61-C (1.0 eq) was used instead of Intermediate Compound 1-C (1.0 eq).
[0753] Synthesis of Intermediate Compound 61-F
[0754] Intermediate Compound 61-F was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-F (yield 78%), except that Intermediate Compound 61-D (1.0 eq) and Intermediate Compound 61-E (1.0 eq) were used instead of Intermediate Compound 1-D (1.0 eq) and Intermediate Compound 1-E (1.0 eq), respectively.
[0755] Synthesis of Intermediate Compound 61-G
[0756] Intermediate Compound 61-G was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-G (yield 75%), except that Intermediate Compound 61-F (1.0 eq) was used instead of Intermediate Compound 1-F (1.0 eq).
[0757] Synthesis of Compound 61
[0758] Compound 61 was synthesized in substantially the same manner as in the synthesis of Compound 1 (yield 34%), except that Intermediate Compound 61-G (1.0 eq) was used instead of Intermediate Compound 1-G (1.0 eq).
[0759] Synthesis Example 3: Synthesis of Compound 81
[0760]
[0761] Synthesis of Intermediate Compound 81-B
[0762] Intermediate Compound 81-B was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-B (yield 48%), except that N,N-dichloromethylamine (MeNCl2) (1.0 eq) was used instead of 2,2-dichloropropane (1.0 eq).
[0763] Synthesis of Intermediate Compound 81-C
[0764] Intermediate Compound 81-C was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-C (yield 82%), except that Intermediate Compound 81-B (1.0 eq) was used instead of Intermediate Compound 1-B (1.0 eq).
[0765] Synthesis of Intermediate Compound 81-D
[0766] Intermediate Compound 81-D was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-D (yield 80%), except that Intermediate Compound 81-C (1.0 eq) was used instead of Intermediate Compound 1-C (1.0 eq).
[0767] Synthesis of Intermediate Compound 81-F
[0768] Intermediate Compound 81-F was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-F (yield 72%), except that Intermediate Compound 81-D (1.0 eq) and Intermediate Compound 61-E (1.0 eq) were used instead of Intermediate Compound 1-D (1.0 eq) and Intermediate Compound 1-E (1.0 eq), respectively.
[0769] Synthesis of Intermediate Compound 81-G
[0770] Intermediate Compound 81-G was synthesized in substantially the same manner as in the synthesis of Intermediate Compound 1-G (yield 71%), except that Intermediate Compound 81-F (1.0 eq) was used instead of Intermediate Compound 1-F (1.0 eq).
[0771] Synthesis of Compound 81
[0772] Compound 81 was synthesized in substantially the same manner as in the synthesis of Compound 1 (yield 29%), except that Intermediate Compound 81-G (1.0 eq) was used instead of Intermediate Compound 1-G (1.0 eq).
[0773] 1H nuclear magnetic resonance spectra (NMR) and mass spectrometry / fast atom bombardment (MS / FAB) of the compounds synthesized according to the synthesis examples are shown in Table 1. By referring to the synthesis routes and raw materials, those skilled in the art can easily identify the synthesis methods of compounds other than the compounds synthesized in the above synthesis examples. 1 The 1H nuclear magnetic resonance spectra (NMR) and mass spectrometry / fast atom bombardment (MS / FAB) of the compounds synthesized according to the synthesis examples are shown in Table 1. By referring to the synthesis routes and raw materials, those skilled in the art can easily identify the synthesis methods of compounds other than the compounds synthesized in the above synthesis examples.
[0774] Table 1
[0775]
[0776] Evaluation Example 1
[0777] The LUMO energy level, HOMO energy level, and maximum emission wavelength (λ max ) value of each of the compounds of the synthesis examples were measured by using the methods described in Table 2, and the metal-to-ligand charge transfer ( 3 MLCT) value of each of the compounds of the synthesis examples was calculated by using the density functional theory (DFT) method of the Gaussian 09 program (structural optimization at the B3LYP, 6-311G(d,p) level). The results are shown in Table 3.
[0778] Table 2
[0779]
[0780]
[0781] Table 3
[0782]
[0783]
[0784] Example 1
[0785] A glass substrate (product of Corning Inc.) with indium tin oxide (ITO) formed thereon as an anode, having a resistance of 15 Ω / cm 2 was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treated with isopropyl alcohol and then with pure water for 5 minutes each, cleaned by irradiation with ultraviolet light and exposure to ozone for 30 minutes, and then mounted on a vacuum deposition apparatus.
[0786] 2-TNATA was vacuum deposited on the anode to form a hole injection layer with a thickness of , and N,N'-bis(1-naphthyl)-N,N'-diphenyl-benzidine (hereinafter referred to as "NPB") was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of .
[0787] The compound ETH2 (second compound), compound HTH29 (third compound), and compound 1 (first compound) are vacuum-deposited on the hole transport layer to form an emission layer having a thickness of. Here, the amount of compound 1 is 10 wt% of the total weight (100 wt%) of the emission layer, and the weight ratio of compound ETH2 and compound HTH29 is adjusted to 3:7.
[0788] Compound ETH2 is vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of , and Alq3 is vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of . LiF is vacuum-deposited on the electron transport layer to form an electron injection layer having a thickness of , and then Al is vacuum-deposited thereon to form a cathode having a thickness of , thus completing the fabrication of the light-emitting device.
[0789]
[0790]
[0791] Example 2
[0792] A light-emitting device is fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, compound EHT66 and compound HTH41 are used instead of compound ETH2 and compound HTH29, respectively, and compound ETH66 and compound HTH41 are deposited simultaneously (e.g., synchronously) at a weight ratio of 3:7 to form an emission layer having a thickness of.
[0793] Example 3
[0794] A light-emitting device is fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, compound ETH2 and compound HTH41 are used instead of compound ETH2 and compound HTH29, respectively, and compound ETH2 and compound HTH41 are deposited simultaneously (e.g., synchronously) at a weight ratio of 3:7 to form an emission layer having a thickness of.
[0795] Example 4
[0796] A light-emitting device is fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, compound ETH66 and compound HTH29 are used instead of compound ETH2 and compound HTH29, respectively, and compound ETH66 and compound HTH29 are deposited simultaneously (e.g., synchronously) at a weight ratio of 3:7 to form an emission layer having a thickness of.
[0797] Example 5
[0798] A light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound 61 (10 wt%) was deposited simultaneously (e.g., synchronously) instead of Compound 1 to form an emission layer having a thickness of
[0799] Example 6
[0800] A light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound 81 (10 wt%) was deposited simultaneously (e.g., synchronously) instead of Compound 1 to form an emission layer having a thickness of
[0801] Example 7
[0802] A light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound ETH2, Compound HTH41, Compound 1, and Compound DFD1 were deposited simultaneously (e.g., synchronously) instead of Compound ETH2, Compound HTH29, and Compound 1 to form an emission layer having a thickness of. Here, the weight ratio of Compound ETH2 and Compound HTH41 was 3:7, and based on the total weight of 100 wt% of the emission layer, the amount of Compound 1 was 10 wt% and the amount of Compound DFD1 was 0.5 wt%.
[0803] Example 8
[0804] A light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound ETH2, Compound HTH66, Compound 1, and Compound DFD1 were deposited simultaneously (e.g., synchronously) instead of Compound ETH2, Compound HTH29, and Compound 1 to form an emission layer having a thickness of. Here, the weight ratio of Compound ETH2 and Compound HTH66 was 3:7, and based on the total weight of 100 wt% of the emission layer, the amount of Compound 1 was 10 wt% and the amount of Compound DFD1 was 0.5 wt%.
[0805] Comparative Example 1
[0806] A light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound ETH2 and Compound 1 (10 wt% based on the total weight of the emission layer of 100 wt%) were deposited simultaneously (e.g., synchronously) instead of Compound ETH2, Compound HTH29, and Compound 1 to form an emission layer having a thickness of
[0807] Comparative Example 2
[0808] The light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound CE1 (10 wt%) was used instead of Compound 1 (10 wt%).
[0809] Comparative Example 3
[0810] The light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound CE2 (10 wt%) was used instead of Compound 1 (10 wt%).
[0811] Comparative Example 4
[0812] The light-emitting device was fabricated in substantially the same manner as in Example 1, except that when forming the emission layer, Compound CE3 (10 wt%) was used instead of Compound 1 (10 wt%).
[0813] Evaluation Example 2
[0814] The driving voltage (V), luminous efficiency (cd / A), maximum emission wavelength (nm), and lifetime (T 90 , h) of each of the light-emitting devices fabricated according to Examples 1 to 8 and Comparative Examples 1 to 4 were measured by using a Keithley MU 236 and a luminance meter PR650, and the results are shown in Table 4. In Table 4, the driving voltage and the luminous efficiency are the driving voltage and the luminous efficiency at a current density of 10 mA / cm 2 , and the lifetime (T 90 ) is a measure of the time taken when the luminance reaches 90% of the initial luminance of 1,000 cd / m 2 .
[0815] Table 4
[0816]
[0817] As can be seen from Table 4, the light-emitting devices according to Examples 1 to 8 each have the characteristics of a low driving voltage, a high luminous efficiency, and a long lifetime.
[0818] As can be seen from Table 4, compared with Comparative Examples 1 to 4, the light-emitting devices according to Examples 1 to 8 each have the characteristics of a lower driving voltage, a higher luminous efficiency, and a comparable or longer lifetime.
[0819] According to one or more embodiments, the use of the organometallic compound represented by Formula 1 can ensure the fabrication of a light-emitting device having a high luminous efficiency and a long lifetime, and a high-quality electronic device including the light-emitting device.
[0820] In the present disclosure, it will be understood that the terms “comprise(s)”, “include(s)”, or “have / has” indicate the presence of the recited features, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof.
[0821] Throughout the present disclosure, when referring to placing a component (such as a layer, film, region, or plate) “on” another component (such as a layer, film, region, or plate), it will be understood that it can be directly on the other component (such as a layer, film, region, or plate) or another component (such as a layer, film, region, or plate) can be interposed therebetween. In some embodiments, “directly on” may mean that there is no additional layer, film, region, plate, etc. between the layer, film, region, plate, etc. and other components. For example, “directly on” may mean that two layers or two members are provided without using an additional member, such as an adhesive member therebetween.
[0822] In the present disclosure, although the terms “first”, “second”, etc. may be used herein to describe one or more elements, components, regions, and / or layers, these elements, components, regions, and / or layers should not be limited by these terms. These terms are only used to distinguish one component from another.
[0823] As used herein, the singular forms “a”, “an”, “one”, and “the” are also intended to include the plural forms, unless the context clearly indicates otherwise. Further, the use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.
[0824] As used herein, the terms “substantially”, “about”, or similar terms are used as approximate terms and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by a person of ordinary skill in the art. As used herein, “about” includes the recited value and means within an acceptable deviation of a particular value as determined by a person of ordinary skill in the art, taking into account the measurements being discussed and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations of the recited value, or within ±30%, ±20%, ±10%, or ±5% of the recited value.
[0825] Any numerical range recited herein is intended to include all sub-ranges subsumed within the recited range having the same degree of numerical precision. For example, a range of "1.0 to 10.0" is intended to include all sub-ranges between and including the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in the present disclosure is intended to include all higher numerical limitations subsumed therein. Accordingly, the applicant reserves the right to modify the present disclosure (including the claims) to expressly recite any sub-range subsumed within the ranges expressly recited herein.
[0826] In the context of the present application, unless otherwise defined, the terms "use", "using", and "used" may each be regarded as synonymous with the term "utilize", "utilizing", and "utilized", respectively.
[0827] The light-emitting device, light-emitting equipment, display device, electronic device, electronic apparatus, or any other related device or component may be implemented using any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Additionally, the various components of the device may be implemented on a flexible printed circuit film, tape carrier package (TCP), or printed circuit board (PCB), or formed on a substrate. Further, the various components of the device may be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions and interacting with other system components to perform the various functions described herein. The computer program instructions are stored in a memory, which may be implemented using standard memory devices in a computing device, such as, for example, random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer-readable media, such as, for example, CD ROM or flash drive, etc. Moreover, those skilled in the art should recognize that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a dedicated computing device may be distributed over one or more other computing devices.
[0828] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and not for purposes of limitation. The description of each feature or aspect in an embodiment is generally to be considered applicable to other similar features or aspects in one or more other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art will understand that one or more suitable changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. A light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; a laminate between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1: Formula 1 wherein, in Formula 1, M1 is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, Ring CY1, ring CY2, and ring CY4 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, X1, X2 and X4 are each independently C or N, Y is *-C(R6)(R7)-*', *-C(=O)-*', *-C(=S)-*', *-B(R6)-*', *-N(R6)-*', *-O-*', *-P(R6)-*', *-Si(R6)(R7)-*', *-Se-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R6)(R7)-*', L1 to L3 are each independently a single bond, *-C(R 1a )(R 1b )-*', *-C(R 1a )=*', *=C(R 1a )-*', *-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*', *-N(R 1a )-*', *-O-*', *-P(R 1a )-*', *-Si(R 1a )(R 1b )-*', *-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', a1 to a3 are each an integer selected from 1 to 3, * and *' each indicate a binding site to an adjacent atom, R1 to R7, R 1a and R 1b each independently is 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 C7-C 60 arylalkyl, 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), -Ge(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Two or more of the plurality of R1s are optionally bonded to each other to form an unsubstituted or R-substituted C3-C 10a carbocyclic group or an unsubstituted or R-substituted C1-C 60 heterocyclic group, 10a 60 Two or more of the plurality of R2 are optionally bonded to each other to form an unsubstituted or at least one R-substituted C3-C 10a carbocyclic group or an unsubstituted or at least one R-substituted C1-C 60 heterocyclic group, 10a 60 Two or more of the plurality of R4s are optionally bonded to each other to form an unsubstituted or at least one R 10a -substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a -substituted C1-C 60 heterocyclic group, R6 and R7 are optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, b1, b2 and b4 are each independently an integer selected from 1 to 10, b3 is 1, b5 is an integer selected from 1 to 3, R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group; Each unsubstituted or substituted by the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(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 unsubstituted or substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(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 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-O(Q 31 )、-S(Q 31 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; or C1-C which is unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
2. The light-emitting device according to claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the laminate further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer or any combination thereof, the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer or any combination thereof, and the emission layer includes the organometallic compound represented by Formula 1.
3. The light-emitting device according to claim 1, wherein the laminate includes: i) a first compound, which is the organometallic compound represented by Formula 1; and ii) comprising at least one π-deficient nitrogen-containing C1-C 60 a second compound having a cyclic group, a third compound having a group represented by Formula 3, a fourth compound emitting delayed fluorescence, or any combination thereof the first compound, the second compound, the third compound and the fourth compound are different from each other: Formula 3 Ring CY in Formula 3 71 and ring CY 72 each independently is a π - electron rich C3 - C 60 cyclic group or a pyridyl group, X in Formula 3 71 is a single bond or a linking group including O, S, N, B, C, Si, or any combination thereof * in Formula 3 indicates a binding site to an adjacent atom in the third compound, and Compound CBP and Compound mCBP are excluded from the third compound:
4. The light-emitting device according to claim 3, wherein the laminate includes the first compound and the fourth compound, and the fourth compound is a compound including at least one cyclic group, and the cyclic group includes boron atom and nitrogen atom as ring-forming atoms respectively.
5. An electronic device, comprising the light-emitting device according to any one of claims 1 to 4.
6. The electronic device according to claim 5, further comprising a thin-film transistor, wherein the thin-film transistor includes a source electrode and a drain electrode, and the first electrode of the light-emitting device is electrically connected to the source electrode or the drain electrode of the thin-film transistor.
7. An organometallic compound represented by Formula 1: Formula 1 Among them, In Formula 1, M1 is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, Ring CY1, ring CY2, and ring CY4 are each independently a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group, X1, X2, and X4 are each independently C or N, Y is *-C(R6)(R7)-*', *-C(=O)-*', *-C(=S)-*', *-B(R6)-*', *-N(R6)-*', *-O-*', *-P(R6)-*', *-Si(R6)(R7)-*', *-Se-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R6)(R7)-*', L1 to L3 are each independently a single bond, *-C(R 1a )(R 1b )-*', *-C(R 1a )=*', *=C(R 1a )-*', *-C(R 1a )=C(R 1b )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 1a )-*', *-N(R 1a )-*', *-O-*', *-P(R 1a )-*', *-Si(R 1a )(R 1b )-*', *-P(=O)(R 1a )-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 1a )(R 1b )-*', a1 to a3 are each an integer selected from 1 to 3, * and *' each indicate a binding site to an adjacent atom, R1 to R7, R 1a and R 1b each independently represents hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, 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 C7-C 60 aralkyl, 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), -Ge(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Two or more of the plurality of R1s are optionally bonded to each other to form an unsubstituted or at least one R 10a -substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a -substituted C1-C 60 heterocyclic group, Two or more of the plurality of R2s are optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, Two or more of the plurality of R4s are optionally bonded to each other to form an unsubstituted or R-substituted C3-C 10a carbocyclic group or an unsubstituted or R-substituted C1-C 60 carbocyclic group or an unsubstituted or R-substituted C1-C 10a heterocyclic group, 60 R6 and R7 are optionally bonded to each other to form an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, b1, b2, and b4 are each independently an integer selected from 1 to 10, b3 is 1, b5 is an integer selected from 1 to 3, R 10a is: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each unsubstituted or substituted with the following C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(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 unsubstituted or substituted with the following C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group or C2-C 60 heteroaralkyl group: deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C7-C 60 aralkyl group, C2-C 60 heteroaralkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(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 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-O(Q 31 )、-S(Q 31 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or C1-C that is unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
8. The organometallic compound according to claim 7, wherein ring CY1 is imidazolyl, benzimidazolyl, imidazopyridyl, imidazopyrazinyl, imidazopyrimidinyl or imidazopyridazinyl, and ring CY2 is phenyl, naphthyl or 1,2,3,4 - tetrahydronaphthyl.
9. The organometallic compound according to claim 7, wherein X1 is C, X2 is C, and X4 is N.
10. The organometallic compound according to claim 7, In Formula 1, the part represented by is a group represented by any one selected from Formula CY(1)-1 to Formula CY(1)-12: In formulas CY(1)-1 to CY(1)-12, R 10 to R 13 each independently is the same as described for R1 in Formula 1, c10 is an integer selected from 1 to 4, c11 is an integer selected from 1 to 3, c12 is an integer of 1 or 2, and * and *' each indicate a binding site to an adjacent atom.
11. The organometallic compound according to claim 7, wherein the part represented by in Formula 1 is a group represented by any one selected from Formula CY(3)-1 to Formula CY(3)-11: In formulas CY(3)-1 to CY(3)-11, R3, R5, and b5 are each the same as described in formula 1, Z1 is the same as described for R6 in formula 1, Z2 is the same as described for R7 in formula 1, Z1 and Z2 are optionally bonded to each other to form an unsubstituted or at least one R 10b substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 60 heterocyclic group, Y 11 is C, Si or Ge, L 11 is *-C(R 6a )(R 7a )-*, *-C(=O)-*, *-C(=S)-*, *-B(R 6a )-*, *-N(R 6a )-*, *-O-*, *-P(R 6a )-*', *-Si(R 6a )(R 7a )-*', *-Se-*', *-S-*', *-S(=O)-*', *-S(=O)2-*' or *-Ge(R 6a )(R 7a )-*', R 31 、R 32 、R 6a and R 7a are each independently: hydrogen, or the same as described for R in Formula 1 10a as described R 6a and R 7a optionally bonded to each other to form an unsubstituted or at least one R 10b substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 60 heterocyclic group, R 10b Each independently is the same as that described for R in Formula 1 10a described c31 and c32 are each independently an integer selected from 1 to 4, and *, *', and *'' each indicate a binding site to an adjacent atom.
12. The organometallic compound according to claim 7, In Formula 1, the part represented by is a group represented by any one selected from Formula CY(4)-1 to Formula CY(4)-16: In formulas CY(4)-1 to CY(4)-16, R 41 to R 44 each is independently the same as described for R4 in Formula 1, but each is not hydrogen, and * and *' each indicate a binding site to an adjacent atom.
13. The organometallic compound according to claim 7, wherein L1 and L3 are each a single bond, and L2 is *-O-*', *-S-*' or *-N(R 1a )-*'.
14. The organometallic compound according to claim 7, wherein the organometallic compound is represented by formula 1-1 or formula 1-2: Formula 1-1 Formula 1-2 In formulas 1-1 and 1-2, M1, ring CY2, ring CY4, X2, X4, Y, L1 to L3, a1 to a3, R2 to R5, and b2 to b5 are each the same as described in formula 1, and R 11 to R 17 Each independently is the same as that described for R1 in Formula 1.
15. The organometallic compound according to claim 7, wherein the organometallic compound is any one selected from Compound 1 to Compound 200:
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