Light emitting device including organometallic compound, electronic device including same, and organometallic compound
By introducing organometallic compounds, especially the compound represented by Formula 1, into light-emitting devices, the carrier recombination efficiency is improved, the shortcomings of existing light-emitting devices in terms of brightness and response speed are solved, and the goal of high-performance light-emitting devices is achieved.
Patent Information
- Application Number
- CN202510310913.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-03-20
- Filing Date
- 2025-03-17
- Publication Date
- 2025-09-23
AI Technical Summary
Existing light-emitting devices have deficiencies in brightness, driving voltage and response speed, making it difficult to meet high performance requirements.
A light emitting device structure including an organic metal compound is adopted, an intermediate layer is provided between the first electrode and the second electrode, and the organic metal compound such as the compound represented by Formula 1 is used to improve the carrier recombination efficiency, thereby improving the luminous efficiency.
The brightness of the light-emitting device is improved, the driving voltage is reduced and the response speed is accelerated, meeting the needs of high-performance light-emitting devices.
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Figure CN120693048A_ABST
Abstract
Description
[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0038305 filed in the Korean Intellectual Property Office on March 20, 2024, the entire contents of which are incorporated herein by reference. Technical Field
[0002] 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 the organometallic compound. Background Art
[0003] Among light-emitting devices, self-emitting devices (e.g., organic light-emitting devices) have relatively wide viewing angles, high contrast ratios, short response times, and excellent or suitable characteristics in terms of brightness, driving voltage, and response speed. That is, self-emitting devices such as organic light-emitting devices stand out among light-emitting devices due to their wide viewing angles, high contrast ratios, fast response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0004] In a light-emitting device, a first electrode is arranged on a substrate, and a hole transport region, an emissive layer, an electron transport region, and a second electrode are sequentially arranged on the first electrode. Holes supplied from the first electrode move toward the emissive layer through the hole transport region, and electrons supplied from the second electrode move toward the emissive layer through the electron transport region. Carriers such as holes and electrons recombine in the emissive layer to produce excitons. The excitons transition from an excited state and relax to a ground state, thereby generating light. Summary of the Invention
[0005] 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 the organometallic compound.
[0006] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the disclosed presented embodiments.
[0007] According to one or more embodiments of the present disclosure, a light emitting device includes:
[0008] a first electrode;
[0009] a second electrode, opposite to the first electrode (e.g., facing the first electrode);
[0010] an intermediate layer between the first electrode and the second electrode and including an emission layer; and
[0011] An organometallic compound represented by Formula 1:
[0012] Formula 1
[0013]
[0014] Formula 2
[0015]
[0016] Among them, in formula 1 and formula 2,
[0017] 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),
[0018] X1 to X4 can each independently be C or N,
[0019] Ring CY1 to Ring CY4 can each independently be C5-C 30 Carbocyclic or C1-C 30 heterocyclic group,
[0020] Ring CY5 can be C3-C 10 Cycloalkyl,
[0021] 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 )-*', where * and *' both represent binding sites with adjacent atoms,
[0022] n1 to n3 may each independently be an integer from 1 to 3,
[0023] R 10 It may be a group represented by Formula 2,
[0024] R1 to R4, Z1 to Z5, R 1aand R 1b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a 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),
[0025] At least one selected from Z2 to Z4 may not be hydrogen,
[0026] Two or more selected from a plurality of R1 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0027] Two or more selected from a plurality of R2 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0028] Two or more selected from a plurality of R3 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0029] Two or more selected from a plurality of R4 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0030] a1 to a4 may each independently be an integer from 1 to 10,
[0031] b1 can be an integer from 1 to 20,
[0032] b5 can be an integer from 1 to 5,
[0033] * indicates the binding site with the adjacent atom,
[0034] R 10a It can be:
[0035] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;
[0036] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy;
[0037] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, -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 C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy or C6-C 60 arylthio; or
[0038] -Si(Q 31 )(Q 32 )(Q 33 ),-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),and
[0039] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 The alkyl radicals may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C2-1-2-1-3-1-4-1-1, which are unsubstituted or substituted with deuterium, -F, cyano, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof. 60 Alkyl, C2-C60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C6 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl.
[0040] According to one or more embodiments of the present disclosure, an electronic apparatus includes a light emitting device.
[0041] According to one or more embodiments of the present disclosure, an organometallic compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS
[0042] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated into and constitute a part of this disclosure. The accompanying 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:
[0043] Figure 1 is a schematic diagram of the structure of an organic light-emitting device according to one or more embodiments of the present disclosure;
[0044] Figure 2 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0045] Figure 3 is a schematic diagram of the structure of a light emitting device according to one or more embodiments of the present disclosure;
[0046] Figure 4 is a schematic perspective view of a structure of electronic equipment including an organic light emitting device according to one or more embodiments of the present disclosure;
[0047] Figure 5 is a schematic diagram of the exterior of a vehicle as electronic equipment including an organic light emitting device according to one or more embodiments of the present disclosure;
[0048] Figures 6A to 6C are schematic diagrams of the interior of a vehicle as electronic equipment including an organic light emitting device according to one or more embodiments of the present disclosure; and
[0049] Figure 7is a schematic diagram of trigonal plane A1 and trigonal plane A2 used for calculating the torsion angle of the disclosed organometallic compound. DETAILED DESCRIPTION
[0050] Reference will now be made in more detail to the embodiments, examples of which are shown in the accompanying drawings, wherein, throughout this disclosure, the same reference numerals refer to the same elements, and for the sake of brevity, a repeated description thereof may not be provided. In this regard, the embodiments presented may have different forms and should not be construed as being limited to the descriptions set forth herein. Therefore, embodiments of the present disclosure will be described only by reference to the accompanying drawings to explain aspects of the present disclosure. As used herein, the terms "and / or" or "or" may include any and all combinations of one or more of the relevant listed items. Throughout the disclosure, expressions such as "at least one (kind / person) of ...", "one (kind / person) of ..." and "selected from ..." modify the entire column of elements when they are after / before a column of elements, without modifying the individual elements of the column. 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 mean only a, only b, only c, both a and b (for example, simultaneously), both a and c (for example, simultaneously), both b and c (for example, simultaneously), all of a, b, and c, or variations thereof. The " / " used herein may be interpreted as "and" or "or," depending on the circumstances.
[0051] According to one or more embodiments of the present disclosure, a light-emitting device (e.g., an organic light-emitting device) may include: a first electrode; a second electrode opposite to the first electrode (e.g., facing the first electrode); an intermediate layer between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1:
[0052] Formula 1
[0053]
[0054] Wherein, in Formula 1, 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).
[0055] In one or more embodiments, M1 may be Pt, Pd, or Au.
[0056] In Formula 1, X1 to X4 may each independently be C or N.
[0057] In one or more embodiments, X1 may be N, X2 may be C, X3 may be C, and X4 may be N.
[0058] In Formula 1, ring CY1 to ring CY4 may each independently be C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group.
[0059] In one or more embodiments, ring CY1 to ring CY4 can each independently be a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzogermanol group, dibenzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzothiophene ... benzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiorrole group, azabenzogermanyl group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, aza heterodibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanyl group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group , quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group or 5,6,7,8-tetrahydroquinoline group.
[0060] In one or more embodiments, ring CY1 can be an imidazole group, a benzimidazole group, an imidazopyridine group, an imidazopyrazine group, an imidazopyrimidine group, or an imidazopyridazine group.
[0061] In one or more embodiments, ring CY2 can be a phenyl group, a naphthalene group, or a 1,2,3,4-tetrahydronaphthalene group.
[0062] In one or more embodiments, ring CY3 can be an indole group, an indene group, a carbazole group, a fluorene group, an azaindole group, an azaindene group, or an azacarbazole group.
[0063] In one or more embodiments, ring CY4 can be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, or an isoquinoline group.
[0064] In one or more embodiments, the formula 1 is The moiety represented by may be a group represented by any one selected from the group consisting of formula CY(1)-1 to formula CY(1)-12:
[0065]
[0066] Among them, in formula CY(1)-1 to formula CY(1)-12,
[0067] R 10 can be the same as described herein,
[0068] R 11 to R 13 may be independently the same as described with reference to R1,
[0069] c10 can be an integer from 1 to 4,
[0070] c11 can be an integer from 1 to 3,
[0071] c12 can be 1 or 2, and
[0072] * and *' both represent binding sites with adjacent atoms. For example, * may represent a binding site with L1 in Formula 1, and *' may represent a binding site with M1 in Formula 1.
[0073] In one or more embodiments, the formula 1 is The moiety represented by may be a group represented by any one selected from formula CY(2)-1 to formula CY(2)-8:
[0074]
[0075] Among them, in formula CY(2)-1 to formula CY(2)-8,
[0076] R 21 to R 23 can be independently the same as described with reference to R2, wherein R 21 to R 23 may not be hydrogen, and
[0077] *, *' and *" all represent binding sites with adjacent atoms. For example, * may represent a binding site with L1 in Formula 1, *' may represent a binding site with M1 in Formula 1, and *" may represent a binding site with L2 in Formula 1.
[0078] In one or more embodiments, the formula 1 is The moiety represented by may be a group represented by any one selected from formula CY(3)-1 to formula CY(3)-7:
[0079]
[0080] Among them, in formula CY(3)-1 to formula CY(3)-7,
[0081] R3 may be the same as described herein,
[0082] c31 can be an integer from 1 to 6,
[0083] c32 can be an integer from 1 to 5, and
[0084] *, *' and *" all represent binding sites with adjacent atoms. For example, * may represent a binding site with L2 in Formula 1, *' may represent a binding site with M1 in Formula 1, and *" may represent a binding site with L3 in Formula 1.
[0085] In one or more embodiments, the formula 1 is The moiety represented by may be a group represented by any one selected from the group consisting of formula CY(4)-1 to formula CY(4)-16:
[0086]
[0087] Among them, in formula CY(4)-1 to formula CY(4)-16,
[0088] R 41 to R 44 can be independently the same as described with reference to R4, wherein R 41 to R 44 may not be hydrogen, and
[0089] * and *' both represent binding sites with adjacent atoms. For example, * may represent a binding site with L3 in Formula 1, and *' may represent a binding site with M1 in Formula 1.
[0090] In one or more embodiments, R is selected from the group consisting of: 41 to R 44 At least one of may be unsubstituted or substituted with at least one R 10a C1-C20 Alkyl is either unsubstituted or substituted with at least one R 10a C6-C 30 Aryl.
[0091] In one or more embodiments, R 42 It can be unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl or any combination thereof, phenyl or naphthyl.
[0092] In one or more embodiments, R 43 It may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl or tert-pentyl, all unsubstituted or substituted with deuterium, phenyl or any combination thereof.
[0093] In Formula 1, 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 )-*', wherein * and *' both represent the binding sites with adjacent atoms.
[0094] In one or more embodiments, L1 and L3 may both be single bonds, and L2 may be *-O-* or *-S-*'.
[0095] In Formula 1, n1 to n3 may each independently be an integer of 1 to 3.
[0096] In Formula 1, if n1 is 2 or greater (for example, when n1 is 2 or greater), two or more of the multiple L1s may be the same as or different from each other, if n2 is 2 or greater (for example, when n2 is 2 or greater), two or more of the multiple L2s may be the same as or different from each other, and if n3 is 2 or greater (for example, when n3 is 2 or greater), two or more of the multiple L3s may be the same as or different from each other.
[0097] In Formula 1, R1 to R4, R 1a and R 1b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a 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).
[0098] In one or more embodiments, R1 to R4, R 1a and R 1b can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 alkoxy;
[0099] All are substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10C1-C1-C1-alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl or pyrimidinyl 20 Alkyl or C1-C 20 alkoxy;
[0100] Unsubstituted or substituted with 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, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, 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, dibenzothienyl, 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 ) and -P(=O)(Q 31 )(Q 32 ) is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, 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, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorol; 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 can all independently be:
[0103] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0104] Unsubstituted or substituted with deuterium, C1-C 10 at least one of an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, and an n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
[0105] In Formula 1, two or more selected from a plurality of R1 may be optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group.
[0106] In Formula 1, two or more selected from a plurality of R2 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10aC1-C 60 Heterocyclic group.
[0107] In Formula 1, two or more selected from a plurality of R3 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group.
[0108] In Formula 1, two or more selected from a plurality of R4 may optionally be combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group.
[0109] In Formula 1, a1 to a4 may each independently be an integer of 1 to 10.
[0110] In formula 1, R 10 It may be a group represented by Formula 2:
[0111] Formula 2
[0112]
[0113] Wherein, in Formula 2, ring CY5 can be C3-C 10 Cycloalkyl.
[0114] In one or more embodiments, ring CY5 can be a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group.
[0115] In Formula 2, Z1 to Z5 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10aC6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a 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), wherein at least one selected from Z2 to Z4 may not be hydrogen.
[0116] In one or more embodiments, Z1 to Z5 can each independently be: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 alkoxy;
[0117] All are substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10 C1-C1-C1-alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl or pyrimidinyl 20 Alkyl or C1-C 20 alkoxy;
[0118] Unsubstituted or substituted with 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, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, 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, dibenzothienyl, 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 ) and -P(=O)(Q 31 )(Q 32 ) is at least one of cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, 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, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiorol; or
[0119] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0120] Q1 to Q3 and Q 31 To Q 33 can all independently be:
[0121] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0122] Unsubstituted or substituted with deuterium, C1-C 10at least one of an alkyl group, a phenyl group, a biphenyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, and a triazinyl group, and an n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, a pyridyl group, a pyrimidyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.
[0123] In one or more embodiments, at least one selected from Z2 to Z4 may be:
[0124] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0125] Unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl or any combination thereof, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl or phenyl.
[0126] In one or more embodiments, at least one selected from Z2 to Z4 may be -CH3, -CD3, -CD2H, -CDH2, or a group represented by any one selected from Formula 8-1 to Formula 8-20:
[0127]
[0128] In Formulae 8-1 to 8-20, D represents deuterium, and * represents a bonding site with an adjacent atom.
[0129] In one or more embodiments, Z5 can be deuterated, unsubstituted, or substituted with at least one R 10a C1-C 20 Alkyl is either unsubstituted or substituted with at least one R 10a C6-C 30 Aryl.
[0130] In Formula 2, b1 may be an integer from 1 to 20.
[0131] In Formula 2, b5 may be an integer from 1 to 5.
[0132] In one or more embodiments, R 10 It may be a group represented by any one selected from Formula 2-1 to Formula 2-4:
[0133]
[0134] Among them, in formula 2-1 to formula 2-4,
[0135] Z1 to Z5 and b5 may all be the same as described herein,
[0136] Z 11 to Z 18 can be independently: deuterium; or C1-C 10 Alkyl, b11 can be an integer from 1 to 7,
[0137] b12 can be an integer from 1 to 5, and
[0138] * indicates the binding site with the adjacent atom.
[0139] In one or more embodiments, R 10 It may be a group represented by any one selected from Formula 2A-1 to Formula 2A-16:
[0140]
[0141] Wherein, in Formula 2A-1 to Formula 2A-16,
[0142] Z2 to Z5 and b5 may all be the same as described herein, D represents deuterium, and
[0143] * indicates the binding site with the adjacent atom.
[0144] In one or more embodiments, R 10 It may be a group represented by any one selected from Formula 2B-1 to Formula 2B-48 and Formula 2C-1 to Formula 2C-48:
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151] Wherein, in Formula 2B-1 to Formula 2B-48 and Formula 2C-1 to Formula 2C-48,
[0152] Z2 to Z4 may all be the same as described herein,
[0153] Z 50 It can be hydrogen, deuterium, or C1-C2-C3-C4-C6-C1-C2 ... 10 alkyl,
[0154] b50 can be an integer from 1 to 5,
[0155] Z 51 It can be hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C 10 Alkyl or unsubstituted or deuterated C6-C 20 Aryl,
[0156] b51 can be an integer from 1 to 4, and
[0157] D represents deuterium, and * represents the binding site with the adjacent atom.
[0158] In one or more embodiments, R 10 Can be any one selected from Group A:
[0159] Group A
[0160]
[0161]
[0162]
[0163]
[0164] Here, in group A, D represents deuterium, and * represents a binding site with an adjacent atom.
[0165] In one or more embodiments, the organometallic compound may be represented by Formula 1-1 or Formula 1-2:
[0166] Formula 1-1
[0167]
[0168] Formula 1-2
[0169]
[0170] Wherein, in Formula 1-1 or Formula 1-2,
[0171] Ring CY2, M1, X2, L1 to L3, n1 to n3, R2, a2 and R 10 may all be the same as described herein,
[0172] R 11 to R 13 may be independently the same as described with reference to R1,
[0173] a13 can be an integer from 1 to 4,
[0174] R 31and R 51 may be independently the same as described with reference to R3,
[0175] a31 may be 1 or 2, and a51 may be an integer from 1 to 4, and
[0176] R 41 to R 44 and R4.
[0177] In one or more embodiments, R selected from Formula 1-1 and Formula 1-2 41 to R 44 At least one of may be unsubstituted or substituted with at least one R 10a C1-C 20 Alkyl is either unsubstituted or substituted with at least one R 10a C6-C 30 Aryl.
[0178] In one or more embodiments, R in Formula 1-1 and Formula 1-2 42 Can be unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl or any combination thereof, phenyl or naphthyl.
[0179] In one or more embodiments, R in Formula 1-1 and Formula 1-2 43 It may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl or tert-pentyl, all unsubstituted or substituted with deuterium, phenyl or any combination thereof.
[0180] In one or more embodiments, the organometallic compound can have a torsion angle of 28 degrees or greater, 29 degrees or greater, 30 degrees or greater, 31 degrees or greater, or 32 degrees or greater.
[0181] In one or more embodiments, the organometallic compound can have a torsion angle of 42 degrees or less, 41 degrees or less, 40 degrees or less, 39 degrees or less, or 38 degrees or less.
[0182] Here, the twist angle refers to an angle formed by a triangular plane A1 simultaneously (eg, concurrently) including the central metal M1 , the ring CY1 , and the ring CY2 in Formula 1 and a triangular plane A2 simultaneously (eg, concurrently) including the central metal M1 , the ring CY3 , and the ring CY4 in Formula 1.
[0183] Here, the torsion angle was calculated using B3LYP / 6-311g(d,p) based on quantum chemical calculations, and the torsion angle was calculated for the structure of the organometallic compound optimized to S0.
[0184] The torsion angles calculated for some organometallic compounds represented by Formula 1 are shown in Table 1. For example, the torsion angles of the compounds in Table 1 are calculated by calculating the angle between the triangular plane A1 and the triangular plane A2 indicated in Formula 1A, and the height and base in Table 1 represent the height length and base length of any triangle formed by the triangular plane A1 and the triangular plane A2 (refer to Figure 7 ).
[0185] Formula 1A
[0186]
[0187] Table 1
[0188] Compound high end Torsion angle (face angle, °) 13 0.81 1.19 34.259 18 1.07 1.67 32.665 76 0.88 1.38 32.541 111 0.80 1.20 33.707 207 1.05 1.29 39.164 257 0.92 1.19 37.727
[0189]
[0190] In one or more embodiments, the organometallic compound can be one of Compound 1 to Compound 408 (eg, selected from any one of Compound 1 to Compound 408):
[0191]
[0192]
[0193]
[0194]
[0195]
[0196]
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225] The organometallic compound represented by Formula 1 may include a group represented by Formula 2.
[0226] Formula 2
[0227]
[0228] The group represented by Formula 2 can be bulky, and the phenyl-containing substituents of benzene A (i.e., benzene substituted with Z2 to Z4) can be located above and below the central metal M1 of the organometallic compound, respectively, so that intermolecular interactions can be suppressed or reduced, thereby preventing or reducing Dexter energy transfer. In addition, the group represented by Formula 2 can include a non-conjugated cycloalkyl group (e.g., a cyclopentyl group or a cyclohexyl group), so that intermolecular interactions can be further suppressed or reduced.
[0229] The group represented by Formula 2 can have an asymmetric structure relative to benzene A (i.e., benzene substituted with Z2 to Z4), so that if electron transfer occurs between molecules (for example, when electron transfer occurs between molecules), Dexter energy transfer can be suppressed or reduced, and the efficiency and life of the light-emitting device using the organic metal compound can be improved.
[0230] Furthermore, due to the asymmetric structure, the stacking effect between molecules can be suppressed or reduced, making it possible to lower the sublimation temperature and deposition temperature of the organometallic compound.
[0231] Therefore, by using the organometallic compound represented by Formula 1, an electronic device (eg, a light emitting device) having high brightness, high efficiency, and long lifespan may be realized.
[0232] Those of ordinary skill in the art can recognize methods for synthesizing the organometallic compound represented by Formula 1 by referring to the synthesis examples and / or examples provided herein.
[0233] In one or more embodiments,
[0234] The first electrode of the light emitting device may be an anode,
[0235] The second electrode of the light emitting device may be a cathode,
[0236] The intermediate layer may further include a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive layer and the second electrode.
[0237] 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, and
[0238] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0239] In one or more embodiments, the intermediate layer of the light emitting device may include the organometallic compound represented by Formula 1.
[0240] In one or more embodiments, the emission layer of the light emitting device may include the organometallic compound represented by Formula 1.
[0241] In one or more embodiments, the emissive layer can emit red, green, blue, and / or white light. For example, in some embodiments, the emissive layer can emit blue light. The blue light can have a maximum emission wavelength in the range of, for example, about 400 nanometers (nm) to about 480 nm.
[0242] In one or more embodiments, the emission layer of the light emitting device may include a dopant and a host, and the organometallic compound represented by Formula 1 may be included in the dopant. For example, in one or more embodiments, the organometallic compound may serve as the dopant.
[0243] In one or more embodiments, the electron transport region of the light emitting device may include a hole blocking layer, which may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, in one or more embodiments, the hole blocking layer may directly contact the emissive layer.
[0244] In one or more embodiments, the intermediate layer in the light emitting device may include: i) a first compound as an organometallic compound represented by Formula 1; and ii) a nitrogen-containing C1-C2-H2O-containing organic compound including at least one π-electron-poor organic compound. 60 a second compound comprising a cyclic group, a third compound comprising 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:
[0245] Formula 3
[0246]
[0247] Among them, the ring CY in formula 3 71 and CY 72 Can be independently π-electron-rich C3-C 60 a cyclic or pyridine group,
[0248] X in Formula 3 71 It can be a single bond or a linker comprising O, S, N, B, C, Si or any combination thereof,
[0249] * in Formula 3 represents a bonding position with an adjacent atom in the remaining portion excluding the group represented by Formula 3 included in the third compound.
[0250] Compound CBP and Compound mCBP are excluded from the third compound:
[0251]
[0252] Description of the second to fourth compounds
[0253] The second compound can include a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or any combination thereof.
[0254] In one or more embodiments, the light emitting device may further include at least one of a second compound and a third compound in addition to the first compound.
[0255] In one or more embodiments, the light emitting device may further include a fourth compound in addition to the first compound.
[0256] In one or more embodiments, the light emitting device may include all of the first to fourth compounds.
[0257] In one or more embodiments, the intermediate layer may include a second compound.In addition to the first compound and the second compound, the intermediate layer may further include a third compound, a fourth compound, and / or a combination thereof (eg, any suitable combination).
[0258] In one or more embodiments, the difference (e.g., the absolute value) between the triplet energy level (eV) of the fourth compound and the singlet energy level (eV) of the fourth compound can be in the range of about 0eV to about 0.5eV (or about 0eV to about 0.3eV).
[0259] In one or more embodiments, the fourth compound may be a compound including at least one cyclic group including both boron (B) and nitrogen (N) as ring atoms (eg, including both boron (B) and nitrogen (N) as ring atoms).
[0260] In one or more embodiments, the fourth compound may be a C8-C8-containing 60 A compound of a polycyclic group, wherein two or more cyclic groups are condensed while sharing boron (B) (for example, one is a first ring and the other is a second ring).
[0261] In one or more embodiments, the fourth compound may include a condensed ring in which at least one third ring is condensed with at least one fourth ring, for example, to form a condensed ring including four or more rings.
[0262] wherein the third ring of the fourth compound may be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a cyclooctene group, an adamantane group, a norbornene group, a norbornane group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group, and
[0263] The fourth ring of the fourth compound may be a 1,2-azaborine group, a 1,3-azaborine group, a 1,4-azaborine group, a 1,2-dihydro-1,2-azaborine group, a 1,4-oxaborine group, a 1,4-thiaborine group, or a 1,4-dihydroborine group.
[0264] In one or more embodiments, the intermediate layer may include a fourth compound.In addition to the first compound and the fourth compound, the intermediate layer may further include a second compound, a third compound, or any combination thereof.
[0265] In one or more embodiments, the intermediate layer may include a third compound. For example, the third compound may not include (eg, may exclude) the compound represented by CBP described herein and the compound represented by mCBP described herein.
[0266] In one or more embodiments, the emission layer in the intermediate layer may include: i) a first compound; and ii) a second compound, a third compound, a fourth compound, or any combination thereof.
[0267] The emission 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.
[0268] In one or more embodiments, the emission layer of the light emitting device may include a first compound and a second compound, and the first compound and the second compound may form an exciplex.
[0269] In one or more embodiments, the emission layer of the light emitting device may include a first compound, a second compound, and a third compound, and the second compound and the third compound may form an exciplex.
[0270] In one or more embodiments, the emission layer of the light emitting device may include the first compound and the fourth compound, and the fourth compound may be used to improve color purity, luminous efficiency, and lifespan characteristics of the light emitting device.
[0271] If a compound (e.g., the fourth compound) including at least one cyclic group containing both boron (B) and nitrogen (N) as ring-forming atoms (e.g., simultaneously containing boron (B) and nitrogen (N) as ring-forming atoms) and an organometallic compound represented by Formula 1 are included together in a dopant (e.g., when a compound (e.g., the fourth compound) including at least one cyclic group containing both boron (B) and nitrogen (N) as ring-forming atoms (e.g., simultaneously containing boron (B) and nitrogen (N) as ring-forming atoms) and an organometallic compound represented by Formula 1 are included together in a dopant), the organometallic compound represented by Formula 1 may function as a sensitizer. If the organometallic compound represented by Formula 1 is used as a sensitizer (e.g., when the organometallic compound represented by Formula 1 is used as a sensitizer), energy of excitons generated in the emission layer may be transferred to the organometallic compound, and then energy may be transferred from the organometallic compound to the remaining other dopant (e.g., the fourth compound), and the remaining other dopant may function as an emitter.
[0272] In one or more embodiments, the second compound may include a compound represented by Formula 2-1:
[0273] Formula 2-1
[0274]
[0275] Among them, in formula 2-1,
[0276] L 61 To L 63 may each independently be a single bond, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0277] b61 to b63 may each independently be an integer from 1 to 5,
[0278] 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 from X 64 To X 66 At least one of the selected ones may be N,
[0279] R 61 to R 66 may all be the same as described herein, and
[0280] R 10aMay be the same as described herein.
[0281] In one or more embodiments, the third compound may include a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, a compound represented by Formula 3-5, or any combination thereof:
[0282] Formula 3-1
[0283]
[0284] Formula 3-2
[0285]
[0286] Formula 3-3
[0287]
[0288] Formula 3-4
[0289]
[0290] Formula 3-5
[0291]
[0292] Among them, in formula 3-1 to formula 3-5,
[0293] CycloCY 71 To Ring CY 74 Can be independently π-electron-rich C3-C 60 a cyclic group or a pyridine group,
[0294] X 82 Can be single bond, O, S, N[(L 82 ) b82 -R 82 ]、C(R 82a )(R 82b ) or Si(R 82a )(R 82b ),
[0295] X 83 Can be single bond, O, S, N[(L 83 ) b83 -R 83 ]、C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),
[0296] X 84 Can be O, S, N[(L84 ) b84 -R 84 ]、C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),
[0297] X 85 Can be C or Si,
[0298] L 81 To L 85 Each of them may be independently a single bond, *-C(Q4)(Q5)-*', *-Si(Q4)(Q5)-*', unsubstituted or substituted with at least one R 10a π-electron-rich C3-C 60 The cyclic group is either unsubstituted or substituted with at least one R 10a A pyridine group, wherein Q4 and Q5 may be the same as those described with reference to Q1,
[0299] b81 to b85 may each independently be an integer from 1 to 5,
[0300] R 71 to R 74 、R 81 to R 85 、R 82a 、R 82b 、R 83a 、R 83b 、R 84a and R 84b may all be the same as described herein,
[0301] a71 to a74 may each independently be an integer from 0 to 20, and
[0302] R 10a May be the same as described herein.
[0303] In one or more embodiments, the fourth compound can be a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof:
[0304] Formula 502
[0305]
[0306] Formula 503
[0307]
[0308] Among them, in formula 502 and formula 503,
[0309] Ring A 501 To Ring A504 Can be independently C3-C 60 Carbocyclic or C1-C 60 heterocyclic group,
[0310] Y 505 Can be O, S, N(R 505 )、B(R 505 )、C(R 505a )(R 505b ) or Si(R 505a )(R 505b ),
[0311] Y 506 Can be O, S, N (R 506 )、B(R 506 )、C(R 506a )(R 506b ) or Si(R 506a )(R 506b ),
[0312] Y 507 Can be O, S, N (R 507 )、B(R 507 )、C(R 507a )(R 507b ) or Si(R 507a )(R 507b ),
[0313] Y 508 Can be O, S, N(R 508 )、B(R 508 )、C(R 508a )(R 508b ) or Si(R 508a )(R 508b ),
[0314] Y 51 and Y 52 may be independently B, P(=O) or S(=O),
[0315] 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 all be the same as described herein,
[0316] a501 to a504 may each independently be an integer from 0 to 20, and
[0317] R 10a May be the same as described herein.
[0318] Description of Equation 2-1, Equation 3, and Equation 4
[0319] In formula 2-1, b61 to b63 represent L 61 Quantity to L 63 and may be an integer from 1 to 5. If b61 is 2 or greater (for example, when b61 is 2 or greater), then multiple L 61 Two or more of L may be the same as or different from each other. If b62 is 2 or greater (for example, when b62 is 2 or greater), then the plurality of L 62 Two or more of L may be the same as or different from each other, and if b63 is 2 or greater (for example, when b63 is 2 or greater), then the plurality of L 63 Two or more of b61 to b63 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.
[0320] In formula 2-1, L 61 To L 63 can all independently be:
[0321] a single key; or
[0322] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophene, dibenzothioyl, dimethyldibenzothioyl, diphenyldibenzothioyl, -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, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, cyclopentadiene group, furan group, thiophene group, thiorrole group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzothiorrole group, dibenzothiorrole group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzothiorrole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group an azole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a dibenzoxinyl group, a dibenzothiinyl group, a dibenzodihydroazacyclohexinyl group, a dibenzodihydrocyclohexinyl group, a dibenzodihydrocyclohexinyl group, a dibenzodioxane group, a dibenzooxathiinyl group, a dibenzoxazine group, a dibenzopyranyl group, a dibenzodithiinyl group, a dibenzothiazine group, a dibenzothiopyranyl group, a dibenzocyclohexadiene group, a dibenzodihydropyridine group, or a dibenzodihydropyrazine group, and
[0323] Q 31 To Q 33 can be independently hydrogen, deuterium, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0324] In one or more embodiments, in Formula 2-1, L 61 With R 61 The key between L 62 With R 62 The key between L 63 With R 63 The key between the two L 61 The key between the two L 62 The key between the two L 63 The key between L 61 and X in formula 2-1 64 and X 65 The carbon bonds between L 62 and X in formula 2-1 64 and X 66 The bonds between carbons and L 63 and X in formula 2-165 and X 66 The bonds between the carbon atoms in the molecule may all be "carbon-carbon single bonds".
[0325] In formula 2-1, 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 from X 64 To X 66 At least one selected from may be N. R 64 to R 66 can be the same as described herein. For example, in one or more embodiments, from X 64 To X 65 Two or three of the selected ones can all be N.
[0326] The R used in this 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 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a 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 all be the same as described herein.
[0327] In one or more embodiments, R in Formula 2-1, Formula 3-1 to Formula 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 、R 508b and R 10a can all independently be:
[0328] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 alkoxy;
[0329] All are substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10 C1-C1 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof 20 Alkyl or C1-C20 alkoxy;
[0330] Unsubstituted or substituted with 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, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, 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, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, 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, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, 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, benzothiophenyl , benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91; or
[0331] -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
[0332] Q1 to Q3 and Q 31 To Q 33 can all independently be:
[0333] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0334] Unsubstituted or substituted with deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl:
[0335] Formula 91
[0336]
[0337] Wherein, in formula 91,
[0338] CycloCY 91 and CY 92 may be independently unsubstituted or substituted with at least one R 10a C5-C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C30 heterocyclic group,
[0339] X 91 Can be single bond, O, S, N(R 91 )、B(R 91 )、C(R 91a )(R 91b ) or Si(R 91a )(R 91b ), R 91 、R 91a and R 91b Can be compared with reference R 82 、R 82a and R 82b Same as described,
[0340] R 10a may be the same as described herein, and
[0341] * indicates the binding site with the adjacent atom.
[0342] In one or more embodiments, in Formula 91,
[0343] CycloCY 91 and CY 92 may be independently unsubstituted or substituted with at least one R 10a a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group or a triazine group, and
[0344] R 91 、R 91a and R 91b can all independently be:
[0345] Hydrogen or C1-C 10 Alkyl; or
[0346] Unsubstituted or substituted with deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.
[0347] In one or more embodiments, R in Formula 2-1, Formula 3-1 to Formula 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 、R 508b and R 10a can all independently be:
[0348] Hydrogen, deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by any one selected from Formula 9-1 to Formula 9-19, a group represented by any one selected from Formula 10-1 to Formula 10-246, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), or -P(=O)(Q1)(Q2) (wherein, Q1 to Q3 may all be the same as described herein):
[0349]
[0350]
[0351]
[0352]
[0353]
[0354]
[0355]
[0356] In Formulae 9-1 to 9-19 and 10-1 to 10-246, * represents a bonding site with an adjacent atom, "Ph" represents a phenyl group, "D" represents deuterium, and "TMS" represents a trimethylsilyl group.
[0357] In Equations 3-1 to 3-5, 502, and 503, a71 to a74 and a501 to a504 represent R 71 The number of R 74 The number of R 501 The number of R 504 and may each independently be an integer from 0 to 20. If a71 is 2 or greater (for example, when a71 is 2 or greater), then the plurality of R 71Two or more of may be the same as or different from each other. If a72 is 2 or greater (for example, when a72 is 2 or greater), then the plurality of R 72 Two or more of may be the same as or different from each other. If a73 is 2 or greater (for example, when a73 is 2 or greater), then multiple R 73 Two or more of may be the same as or different from each other. If a74 is 2 or greater (for example, when a74 is 2 or greater), then multiple R 74 Two or more of R may be the same as or different from each other. If a501 is 2 or greater (for example, when a501 is 2 or greater), then the plurality of R 501 Two or more of R may be the same as or different from each other. If a502 is 2 or greater (for example, when a502 is 2 or greater), then the plurality of R 502 Two or more of R may be the same as or different from each other. If a503 is 2 or greater (for example, when a503 is 2 or greater), then the plurality of R 503 Two or more of R may be the same as or different from each other. If a504 is 2 or greater (for example, when a504 is 2 or greater), then the plurality of R 504 In one or more embodiments, a71 to a74 and a501 to a504 may each independently be an integer from 0 to 8.
[0358] In one or more embodiments, in Formula 2-1, *-(L 61 ) b61 -R 61 The group represented by *-(L 62 ) b62 -R 62 The groups represented by may not all be phenyl.
[0359] In one or more embodiments, in Formula 2-1, *-(L 61 ) b61 -R 61 The group represented by *-(L 62 ) b62 -R 62 The groups represented by may be the same as each other.
[0360] In one or more embodiments, in Formula 2-1, *-(L 61 ) b61 -R 61 The group represented by *-(L 62 ) b62 -R 62 The groups represented may be different from each other.
[0361] In one or more embodiments, in Formula 2-1, b61 and b62 may both be 1, 2, or 3, and L 61 and L 62 may be independently unsubstituted or substituted with at least one R 10a a phenyl group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group or a triazine group.
[0362] In one or more embodiments, R in Formula 2-1 61 and R 62 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a C6-C 60 arylthio, -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3),
[0363] Q1 to Q3 can be independently unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C alkoxy, phenyl, biphenyl or any combination thereof 60 Carbocyclic or C1-C 60 Heterocyclic group.
[0364] In one or more embodiments,
[0365] In formula 2-1, *-(L 61 ) b61 -R 61 The group represented may be a group represented by any one selected from Formula CY51-1 to Formula CY51-26, and / or
[0366] In formula 2-1, *-(L 62 ) b62 -R 62 The group represented by may be a group represented by any one selected from Formula CY52-1 to Formula CY52-26, and / or
[0367] In formula 2-1, *-(L 63 ) b63 -R 63The group represented may be a group represented by any one selected from the group consisting of Formula CY53-1 to Formula CY53-27, -C(Q1)(Q2)(Q3), or -Si(Q1)(Q2)(Q3):
[0368]
[0369]
[0370]
[0371] Among them, in Formulas CY51-1 to CY51-26, Formulas CY52-1 to CY52-26, and Formulas CY53-1 to CY53-27,
[0372] Y 63 Can be single bond, O, S, N(R 63 )、B(R 63 )、C(R 63a )(R 63b ) or Si(R 63a )(R 63b ),
[0373] Y 64 Can be single bond, O, S, N(R 64 )、B(R 64 )、C(R 64a )(R 64b ) or Si(R 64a )(R 64b ),
[0374] Y 67 Can be single bond, O, S, N(R 67 )、B(R 67 )、C(R 67a )(R 67b ) or Si(R 67a )(R 67b ), Y 68 Can be single bond, O, S, N(R 68 )、B(R 68 )、C(R 68a )(R 68b ) or Si(R 68a )(R 68b ),
[0375] Y in formula CY51-16 and formula CY51-17 63 and Y 64 Each of may not be a single bond at the same time,
[0376] Y in formula CY52-16 and formula CY52-1767 and Y 68 Each of may not be a single bond at the same time,
[0377] R 51a to R 51e 、R 61 to R 64 、R 63a 、R 63b 、R 64a and R 64b Can be compared with R in formula 2-1 61 Same as described, where R 51a to R 51e may not be hydrogen,
[0378] R 52a to R 52e 、R 65 to R 68 、R 67a 、R 67b 、R 68a and R 68b Can be compared with R in formula 2-1 62 Same as described, where R 52a to R 52e may not be hydrogen,
[0379] R 53a to R 53e 、R 69a and R 69b Can be compared with R in formula 2-1 63 Same as described, where R 53a to R 53e may not be hydrogen, and
[0380] * indicates the binding site with the adjacent atom.
[0381] In one or more embodiments,
[0382] In Formulas CY51-1 to CY51-26 and CY52-1 to CY52-26, R 51a to R 51e and R 52a to R 52e can all independently be:
[0383] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzo cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, 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, benzothiophenyl , benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl, azadibenzothiorolyl, or a group represented by Formula 91; or
[0384] -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3),
[0385] Q1 to Q3 can be independently unsubstituted or substituted with deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl,
[0386] In formula CY51-16 and formula CY51-17, i) Y 63 Can be O or S, and Y 64 It can be Si(R64a )(R 64b ), or ii) Y 63 It can be Si(R 63a )(R 63b ), and Y 64 Can be O or S, and
[0387] In formula CY52-16 and formula CY52-17, i) Y 67 Can be O or S, and Y 68 It can be Si(R 68a )(R 68b ), or ii) Y 67 It can be Si(R 67a )(R 67b ), and Y 68 Can be O or S.
[0388] In one or more embodiments, in Formula 3-1 to Formula 3-5, L 81 To L 85 can all independently be:
[0389] single bond;
[0390] *-C(Q4)(Q5)-*' or *-Si(Q4)(Q5)-*'; or
[0391] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophene, dibenzothioyl, dimethyldibenzothioyl, diphenyldibenzothioyl, -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, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a cyclopentadiene group, a furan group, a thiophene group, a thiorrole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzothiorrole group, a dibenzothiorrole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzothiorrole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group, and
[0392] Q4, Q5 and Q 31 To Q 33 can be independently hydrogen, deuterium, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.
[0393] In one or more embodiments, the formulas 3-1 and 3-2 are given by The group represented may be a group represented by any one selected from the group consisting of formula CY71-1(1) to formula CY71-1(8), and / or
[0394] In formula 3-1 and formula 3-3, The group represented may be a group represented by any one of formula CY71-2(1) to formula CY71-2(8), and / or
[0395] In formula 3-2 and formula 3-4, The group represented may be a group represented by any one selected from the group consisting of formula CY71-3(1) to formula CY71-3(32), and / or
[0396] In formula 3-3 to formula 3-5, The group represented may be a group represented by any one selected from the group consisting of formula CY71-4(1) to formula CY71-4(32), and / or
[0397] In formula 3-5, The group represented may be a group represented by any one selected from the group consisting of formula CY71-5(1) to formula CY71-5(8):
[0398]
[0399]
[0400]
[0401]
[0402] Among them, in 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),
[0403] X 81 To X 85 , L 81 、b81、R 81 and R 85 may all be the same as described herein,
[0404] X 86 Can be single bond, O, S, N(R 86 )、B(R 86 )、C(R 86a )(R 86b ) or Si(R 86a )(R 86b ),
[0405] X 87 Can be single bond, O, S, N(R 87 )、B(R 87 )、C(R 87a )(R 87b ) or Si(R 87a )(R 87b ),
[0406] X in each of Formula CY71-1(1) to Formula CY71-1(8) and Formula CY71-4(1) to Formula CY71-4(32) 86 and X 87 Each of may not be a single bond at the same time,
[0407] X 88 Can be single bond, O, S, N(R 88 )、B(R 88 )、C(R 88a )(R 88b ) or Si(R 88a )(R 88b ),
[0408] X 89 Can be single bond, O, S, N(R 89)、B(R 89 )、C(R 89a )(R 89b ) or Si(R 89a )(R 89b ),
[0409] X in each of Formula CY71-2(1) to Formula CY71-2(8), Formula CY71-3(1) to Formula CY71-3(32), and Formula CY71-5(1) to Formula CY71-5(8) 88 and X 89 Each of may not be a single bond at the same time, and
[0410] R 86 to R 89 、R 86a 、R 86b 、R 87a 、R 87b 、R 88a 、R 88b 、R 89a and R 89b Can be compared with reference R 81 Same as described.
[0411] Examples of the second to fourth compounds
[0412] In one or more embodiments, the second compound may include (e.g., selected from) at least one of compounds ETH1 to ETH85:
[0413]
[0414]
[0415]
[0416]
[0417] In one or more embodiments, the third compound may include (e.g., be selected from) at least one of compounds HTH1 to HTH53:
[0418]
[0419]
[0420]
[0421] In one or more embodiments, the fourth compound may include (e.g., be selected from) at least one of compound DFD1 to compound DFD14:
[0422]
[0423] In the above compounds, "Ph" represents a phenyl group, "D5" represents substitution with 5 deuterium atoms, and "D4" represents substitution with 4 deuterium atoms. The group represented by The groups represented are the same.
[0424] In one or more embodiments, the light emitting device may satisfy at least one selected from Condition 1 to Condition 4:
[0425] Condition 1
[0426] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound is greater than the LUMO energy level (eV) of the first compound.
[0427] Condition 2
[0428] LUMO energy level (eV) of the first compound > LUMO energy level (eV) of the second compound
[0429] Condition 3
[0430] The highest occupied molecular orbital (HOMO) energy level (eV) of the first compound is greater than the HOMO energy level (eV) of the third compound.
[0431] Condition 4
[0432] The HOMO energy level (eV) of the third compound is greater than the HOMO energy level (eV) of the second compound.
[0433] The HOMO energy level and the LUMO energy level of each of the first compound, the second compound, and the third compound may both be negative values, and may both be values measured according to an appropriate method or values estimated using a density functional theory (DFT) method.
[0434] In one or more embodiments, the absolute value of the difference between the LUMO energy level of the first compound (i.e., the organometallic compound) and the LUMO energy level of the second compound may be in the range of about 0.1 eV to about 1.0 eV, 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 in the range of about 0.1 eV to about 1.0 eV, 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 (e.g., about 0.2 eV to about 1.25 eV), and 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 (e.g., about 0.2 eV to about 1.25 eV).
[0435] When the relationship between the LUMO energy level and the HOMO energy level satisfies the conditions described above, a balance between holes and electrons injected into the emission layer can be achieved.
[0436] The light emitting device may have the structure of the first embodiment or the second embodiment. Details of the first embodiment or the second embodiment may be the same as those described herein.
[0437] Description of the First Embodiment
[0438] According to a first embodiment, a first compound (e.g., an organometallic compound) may be included in an emission layer in an intermediate layer of a light-emitting device, wherein the emission layer may further include a host, the first compound and the host may be different from each other, and the emission layer may emit phosphorescence or fluorescence emitted from the first compound. For example, according to the first embodiment, the first compound may be a dopant or an emitter. For example, in one or more embodiments, the first compound may be a phosphorescent dopant or a phosphorescent emitter.
[0439] In one or more embodiments, the phosphorescence or fluorescence emitted from the first compound can be blue light.
[0440] In one or more embodiments, the emission layer may further include an auxiliary dopant. The auxiliary dopant may be used to improve the light emission efficiency of the first compound by efficiently transferring energy to the first compound as a dopant or emitter.
[0441] The auxiliary dopant may be different from the first compound and the host.
[0442] In one or more embodiments, the auxiliary dopant may be a delayed fluorescence emission compound.
[0443] In one or more embodiments, the auxiliary dopant may be a compound including at least one cyclic group including both boron (B) and nitrogen (N) as ring atoms (eg, including both boron (B) and nitrogen (N) as ring atoms).
[0444] Description of the Second Embodiment
[0445] According to a second embodiment, a first compound (e.g., an organic metal compound) may be included in an emission layer in an intermediate layer of a light-emitting device, wherein 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) emitted from the dopant.
[0446] In one or more embodiments, the first compound in the second embodiment may function not as a dopant but as an assisting dopant that transfers energy to a dopant (or emitter).
[0447] In one or more embodiments, the first compound in the second embodiment can function as an emitter and can also function as an assist dopant that transfers energy to the dopant (or emitter).
[0448] 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 (eg, blue delayed fluorescence).
[0449] The dopant (or emitter) in the second embodiment can be a phosphorescent dopant material (e.g., an organometallic compound represented by Formula 1, an organometallic compound represented by Formula 401, or any combination thereof) or any fluorescent dopant material (e.g., a compound represented by Formula 501, a compound represented by Formula 502, a compound represented by Formula 503, or any combination thereof).
[0450] The blue light in the first and second embodiments may be blue light having a maximum emission wavelength within a range of about 430 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.
[0451] The auxiliary dopant in the first embodiment may include, for example, a fourth compound represented by Formula 502 or Formula 503.
[0452] The host in the first and second embodiments may be any host material (eg, the compound represented by Formula 301, the compound represented by Formula 301-1, the compound represented by Formula 301-2, or any combination thereof).
[0453] In one or more embodiments, the host in the first embodiment and the second embodiment can be the second compound, the third compound, or any combination thereof.
[0454] In one or more embodiments, the light emitting device may further include a cover layer disposed outside (eg, on) the first electrode and / or outside (eg, on) the second electrode.
[0455] In one or more embodiments, the light-emitting device may further include at least one of a first covering layer disposed outside (e.g., on) the first electrode and a second covering layer disposed outside (e.g., on) the second electrode, wherein at least one of the first covering layer and the second covering layer may include an organometallic compound represented by Formula 1. More details about the first covering layer and / or the second covering layer may be the same as described herein.
[0456] In one or more embodiments, the light emitting device may further include a first capping layer disposed outside (eg, on) the first electrode. For example, the first capping layer may include an organic metal compound represented by Formula 1.
[0457] In one or more embodiments, the light emitting device may further include a second capping layer disposed outside (eg, on) the second electrode. For example, the second capping layer may include an organic metal compound represented by Formula 1.
[0458] In one or more embodiments, the light emitting device may further include a first covering layer disposed outside (e.g., on) the first electrode and a second covering layer disposed outside (e.g., on) the second electrode. For example, at least one of the first covering layer and the second covering layer may include an organic metal compound represented by Formula 1.
[0459] The expression “(the intermediate layer and / or the covering layer) includes an organometallic compound” as used herein may be understood as “(the intermediate layer and / or the covering layer) may include one organometallic compound represented by Formula 1 or two or more different kinds of organometallic compounds each represented by Formula 1”.
[0460] In one or more embodiments, the intermediate layer and / or the covering layer may include only Compound 1 as the organometallic compound. In this regard, Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the intermediate layer may include Compound 1 and Compound 2 as organometallic compounds. 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).
[0461] The term "intermediate layer" as used herein refers to a single layer and / or all of a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0462] Figure 1 Description
[0463] Figure 1 is a schematic cross-sectional view of a light emitting device 10 according to one or more embodiments. The light emitting device 10 may include a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .
[0464] In the following, reference will be made to Figure 1 A structure of a light emitting device 10 and a method of manufacturing the light emitting device 10 according to one or more embodiments are described.
[0465] First electrode 110
[0466] exist Figure 1 In one or more embodiments, a substrate may be further provided and arranged below the first electrode 110 and / or on the second electrode 150. A glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include a plastic having excellent or suitable heat resistance and durability (such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof).
[0467] The first electrode 110 may be formed by, for example, depositing or sputtering, on a substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0468] The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In one or more embodiments, if the first electrode 110 is a transmissive electrode (e.g., when the first electrode 110 is a transmissive electrode), the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, if the first electrode 110 is a transflective electrode or a reflective electrode (e.g., when the first electrode 110 is a transflective electrode or a reflective electrode), the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0469] The first electrode 110 may have a single-layer structure including a single layer (eg, consisting of a single layer) or a multi-layer structure including a plurality of layers. For example, in some embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0470] Middle layer 130
[0471] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0472] In one or more embodiments, the intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0473] In one or more embodiments, in addition to one or more suitable organic materials, the intermediate layer 130 may also include metal-containing compounds (such as organometallic compounds (e.g., organometallic compounds represented by Formula 1)) and / or inorganic materials (such as quantum dots), etc.
[0474] In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer disposed between the two or more emission units. When the intermediate layer 130 includes the emission units and the charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[0475] Hole transport region in the intermediate layer 130
[0476] The hole transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including multiple materials different from each other; or iii) a multilayer structure including multiple layers including multiple materials different from each other.
[0477] 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.
[0478] In one or more embodiments, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission 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 / emission assisting layer structure, wherein the constituent layers of each structure are stacked sequentially from the first electrode 110 in the order stated.
[0479] 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:
[0480] Formula 201
[0481]
[0482] Formula 202
[0483]
[0484] Among them, in Equation 201 and Equation 202,
[0485] L 201 To L 204may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0486] L 205 Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or substituted with at least one R 10a C1-C 20 Alkylene, unsubstituted or substituted with at least one R 10a C2-C 20 Alkenylene, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0487] xa1 to xa4 may each independently be an integer from 0 to 5,
[0488] xa5 can be an integer from 1 to 10,
[0489] R 201 to R 204 and Q 201 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0490] R 201 and R 202 may optionally be substituted via a single bond, unsubstituted or substituted with at least one R 10a The C1-C5 alkylene group is either unsubstituted or substituted with at least one R 10a The C2-C5 alkenylene groups are connected to each other to form an unsubstituted or substituted group with at least one R 10a C8-C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., see compound HT16, etc.),
[0491] R 203 and R 204 may optionally be substituted via a single bond, unsubstituted or substituted with at least one R 10a The C1-C5 alkylene group is either unsubstituted or substituted with at least one R 10a The C2-C5 alkenylene groups are connected to each other to form an unsubstituted or substituted group with at least one R10a C8-C 60 Polycyclic groups, and
[0492] na1 can be an integer from 1 to 4.
[0493] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formulas CY201 to CY217:
[0494]
[0495] Among them, in formula CY201 to formula CY217, R 10b and R 10c Can be compared with reference R 10a Same as described, CY 201 To Ring CY 204 Can be independently C3-C 20 Carbocyclic or C1-C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.
[0496] In one or more embodiments, ring CY in Formula CY201 to Formula CY217 201 To Ring CY 204 Each of them may independently be a phenyl group, a naphthalene group, a phenanthrene group or an anthracene group.
[0497] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one selected from the groups represented by Formulas CY201 to CY203.
[0498] In one or more embodiments, Formula 201 may include at least one selected from the groups represented by Formulas CY201 to CY203 and at least one selected from the groups represented by Formulas CY204 to CY217.
[0499] In one or more embodiments, in Formula 201, xa1 may be 1, R 201 It can be a group represented by any one of formula CY201 to formula CY203, xa2 can be 0, R 202 It may be a group represented by any one selected from Formula CY204 to Formula CY207.
[0500] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any one of the groups represented by Formula CY201 to Formula CY203.
[0501] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any one of the groups represented by Formula CY201 to Formula CY203, and may include at least one selected from the groups represented by Formula CY204 to Formula CY217.
[0502] In one or more embodiments, each of Formula 201 and Formula 202 may not include (eg, may exclude) any one of the groups represented by Formula CY201 to Formula CY217.
[0503] In one or more embodiments, the hole transport region may include at least one of compounds HT1 to HT46 (e.g., selected from compounds HT1 to 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'-di(naphth-1-yl)-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'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC); 4,4'-bis[N,N'-(3-methylphenyl)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:
[0504]
[0505]
[0506]
[0507]
[0508]
[0509] The thickness of the hole transport region can 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 can be in the range of 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 ranges described above, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0510] The emission-assisting layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the leakage of electrons from the emission layer 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.
[0511] p-dopant
[0512] In one or more embodiments, in addition to one or more materials described above, the hole transport region may further include a charge generating material for improving the conductive properties. The charge generating 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 including (e.g., consisting of) the charge generating material).
[0513] The charge generating material may be, for example, a p-dopant.
[0514] In one or more embodiments, the p-dopant may have a LUMO level of -3.5 eV or less.
[0515] In one or more embodiments, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.
[0516] Non-limiting examples of the quinone derivative may include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ).
[0517] Non-limiting examples of cyano group-containing compounds may include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and compounds represented by Formula 221:
[0518]
[0519] Formula 221
[0520]
[0521] Where, in formula 221,
[0522] R 221 to R 223 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, and
[0523] Selected from R 221 to R 223 At least one of them may be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C1-C1-C1-substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 20 alkyl; or any combination thereof.
[0524] In a compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or (eg, any suitable) combination thereof, and element EL2 may be a nonmetal, a metalloid, or (eg, any suitable) combination thereof.
[0525] 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.); late 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.).
[0526] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0527] Non-limiting examples of non-metals may include oxygen (O) and halogens (eg, F, Cl, Br, and / or I, etc.).
[0528] Non-limiting examples of compounds including 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.
[0529] Non-limiting examples of metal oxides may include tungsten oxide (e.g., WO, W2O3, WO2, WO3 and / or W2O5, etc.), vanadium oxide (e.g., VO, V2O3, VO2 and / or V2O5, etc.), molybdenum oxide (e.g., MoO, Mo2O3, MoO2, MoO3 and / or Mo2O5, etc.), and rhenium oxide (e.g., ReO3, etc.).
[0530] Non-limiting examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, late transition metal halides, and lanthanide metal halides.
[0531] Non-limiting examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
[0532] Non-limiting examples of alkaline earth halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.
[0533] Non-limiting examples of transition metal halides may 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, T aBr3 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, etc.), and / or ReI2, etc.), ferrous 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, etc.), 2 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.), cuprous halides (e.g., CuF, CuCl, CuBr and / or CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr and / or AgI, etc.) and gold halides (e.g., AuF, AuCl, AuBr and / or AuI, etc.).
[0534] Non-limiting examples of late transition metal halides may include zinc halides (eg, ZnF2, ZnCl2, ZnBr2, and / or ZnI2, etc.), indium halides (eg, InI3, etc.), and tin halides (eg, SnI2, etc.).
[0535] Non-limiting examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
[0536] Non-limiting examples of the metalloid halide may include antimony halide (eg, SbCl 5 , etc.).
[0537] 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.), late transition metal tellurides (e.g., ZnTe, etc.) and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.).
[0538] Emission layer in the middle layer 130
[0539] When the light-emitting device 10 is a full-color light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from the red emission layer, the green emission layer and the blue emission layer to emit white light (e.g., combined white light), wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from the red light-emitting material, the green light-emitting material and the blue light-emitting material to emit white light (e.g., combined white light), wherein the two or more materials are mixed with each other in a single layer.
[0540] The emissive layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0541] The amount of the dopant in the emission layer may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0542] In one or more embodiments, the emissive layer may include quantum dots.
[0543] In one or more embodiments, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emissive layer.
[0544] The thickness of the emission layer can be about to about (For example, about to about When the thickness of the emission layer is within the range described above, excellent or suitable light emitting characteristics may be obtained without significantly increasing the driving voltage.
[0545] main body
[0546] In one or more embodiments, the host may include a compound represented by Formula 301:
[0547] Formula 301
[0548] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0549] Wherein, in formula 301,
[0550] Ar 301 and L 301 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0551] xb11 can be 1, 2 or 3,
[0552] xb1 can be an integer from 0 to 5,
[0553] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, -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 ),
[0554] xb21 can be an integer from 1 to 5, and
[0555] Q 301 To Q 303 All may be the same as described with reference to Q1.
[0556] In one or more embodiments, if xb11 in equation 301 is 2 or greater (eg, when xb11 in equation 301 is 2 or greater), then the plurality of Ar 301 Two or more of may be linked to each other via a single bond.
[0557] 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:
[0558] Formula 301-1
[0559]
[0560] Formula 301-2
[0561]
[0562] In Formula 301-1 and Formula 301-2,
[0563] Ring A 301 To Ring A 304 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0564] X301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0565] xb22 and xb23 can each independently be 0, 1 or 2,
[0566] L 301 , xb1 and R 301 may all be the same as described herein,
[0567] L 302 To L 304 Can be independently compared with reference L 301 Same as described,
[0568] xb2 to xb4 may each independently be the same as described with reference to xb1, and
[0569] R 302 to R 305 and R 311 to R 314 Can be compared with reference R 301 Same as described.
[0570] In one or more embodiments, the host can include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, in some embodiments, the host can include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0571] In one or more embodiments, the host may include: at least one of Compound H1 to Compound H124 (e.g., selected from Compound H1 to Compound H124); 9,10-di(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN); 9,10-di(2-naphthyl)-2-tert-butylanthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-di(carbazol-9-yl)benzene (mCP); 1,3,5-tri(carbazol-9-yl)benzene (TCP); or any combination thereof:
[0572]
[0573]
[0574]
[0575]
[0576]
[0577]
[0578] Phosphorescent dopants
[0579] The phosphorescent dopant may include an organometallic compound represented by Formula 1.
[0580] The phosphorescent dopant may be electrically neutral.
[0581] In one or more embodiments, the phosphorescent dopant may further include an organometallic compound represented by Formula 401:
[0582] Formula 401
[0583] M(L 401 ) xc1 (L 402 ) xc2
[0584] Formula 402
[0585]
[0586] Among them, in formula 401 and formula 402,
[0587] M can 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)),
[0588] L 401 may be a ligand represented by formula 402, and xc1 may be 1, 2, or 3, wherein if xc1 is 2 or greater (eg, when xc1 is 2 or greater), then a plurality of L 401 Two or more of may be the same as or different from each other,
[0589] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3 or 4, wherein if xc2 is 2 or greater (for example, when xc2 is 2 or greater), then the plurality of L 402 Two or more of may be the same as or different from each other,
[0590] X 401 and X 402 may each independently be nitrogen or carbon,
[0591] Ring A 401 and Ring A402 Can be independently C3-C 60 Carbocyclic or C1-C 60 heterocyclic group,
[0592] T 401 It can 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 )-*',
[0593] X 403 and X 404 can each independently be a chemical bond (eg, a covalent bond or a coordinate bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0594] Q 411 To Q 414 can be the same as described in reference Q1,
[0595] R 401 and R 402 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 20 Alkyl, unsubstituted or substituted with at least one R 10a C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 ),-C(=O)(Q 401 )、-S(=O)2(Q 401) or -P(=O)(Q 401 )(Q 402 ),
[0596] Q 401 To Q 403 can be the same as described in reference Q1,
[0597] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0598] * and *' in Formula 402 both represent the binding sites with M in Formula 401.
[0599] In one or more embodiments, in formula 402, i) X 401 can be nitrogen, and X 402 Can be carbon, or ii) X 401 and X 402 Each of can be nitrogen.
[0600] In one or more embodiments, if xc1 in equation 401 is 2 or greater (eg, when xc1 in equation 401 is 2 or greater), then the plurality of L 401 Two or more of the two ring A 401 It can optionally be linked via T 402 connected to each other, and / or two rings A 402 It can optionally be connected via T as a linker 403 Connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be compared with reference T 401 Same as described.
[0601] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include a halogen, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus-containing group (e.g., a phosphine group and / or a phosphite group, etc.), or any combination thereof.
[0602] In one or more embodiments, the phosphorescent dopant may include, for example, at least one of Compound PD1 to Compound PD39 (selected from Compound PD1 to Compound PD39) or any combination thereof:
[0603]
[0604]
[0605]
[0606] Fluorescent dopants
[0607] The fluorescent dopant may include an amine-containing compound, a styryl-containing compound, or any combination thereof.
[0608] For example, in one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:
[0609] Formula 501
[0610]
[0611] Wherein, in formula 501,
[0612] Ar 501 , L 501 To L 503 、R 501 and R 502 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0613] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0614] xd4 can be 1, 2, 3, 4, 5 or 6.
[0615] In one or more embodiments, Ar in Formula 501 501 It may be a condensed ring group in which three or more monocyclic groups are condensed with each other (for example, anthracene group, groups and / or pyrene groups, etc.).
[0616] In one or more embodiments, xd4 in equation 501 may be 2.
[0617] In one or more embodiments, the fluorescent dopant may include: at least one of Compound FD1 to Compound FD36 (e.g., selected from Compound FD1 to Compound FD36); 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi); 4,4'-bis[4-(N,N-diphenylamino)phenylvinyl]biphenyl (DPAVBi); or any combination thereof:
[0618]
[0619]
[0620]
[0621] Delayed fluorescence materials
[0622] In one or more embodiments, the emissive layer may include a delayed fluorescent material.
[0623] Here, the delayed fluorescent material may be any one selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0624] The delayed fluorescent material included in the emission layer may act as a host or a dopant according to the types or kinds of other materials included in the emission layer.
[0625] In one or more embodiments, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material (eV) (e.g., the absolute value of the difference) may be in the range of about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material is within the range described above, upconversion of the delayed fluorescent material from the triplet state to the singlet state may occur effectively, and thus, the light-emitting device 10 may have improved luminous efficiency.
[0626] In one or more embodiments, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C3-C 60 cyclic group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group and / or a π-electron-poor nitrogen-containing C1-C 60 and / or ii) materials comprising C8-C8 wherein two or more cyclic groups are condensed while sharing boron (B); 60 Polycyclic materials.
[0627] Non-limiting examples of the delayed fluorescent material may include at least one of Compound DF1 to Compound DF9 (eg, selected from Compound DF1 to Compound DF9):
[0628]
[0629] quantum dots
[0630] In one or more embodiments, the emissive layer may include quantum dots.
[0631] The term "quantum dot" as used herein refers to a crystal of a semiconductor compound and may include any material capable of emitting light at one or more suitable emission wavelengths depending on the size of the crystal.
[0632] The diameter of the quantum dot can be, for example, in the range of about 1 nm to about 10 nm. In the present disclosure, when a quantum dot, a plurality of quantum dots or quantum dot particles are spherical, "diameter" means the particle size or the average particle size, and when the particles are non-spherical, "diameter" means the major axis length or the 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, a HORIBALA-950 laser particle size analyzer can be used. When the size of the particles is measured using a particle size analyzer, the average particle size is referred to as D50. D50 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 particle when the total number of particles is 100% in the distribution curve accumulated in the order from the smallest particle size to the largest particle size.
[0633] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0634] The wet chemical process is a method that involves mixing a quantum dot precursor material with an organic solvent and then growing quantum dot particle crystals. As the quantum dot particle crystals grow, the organic solvent naturally acts as a dispersant that coordinates on the surface of the quantum dot particle crystals and controls the growth of the quantum dot particle crystals. Therefore, the growth of quantum dot particle crystals can be controlled or selected through a process that is less expensive and easier than vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0635] Quantum dots may 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.
[0636] Non-limiting examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and / or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe; and / or any combination thereof.
[0637] Non-limiting examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb; ternary compounds such as GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNPs, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds such as GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; and / or any combination thereof. In one or more embodiments, the III-V semiconductor compounds may further include a Group II element. Non-limiting examples of Group III-V semiconductor compounds that also include Group II elements may include InZnP, InGaZnP, and / or InAlZnP.
[0638] Non-limiting examples of III-VI semiconductor compounds may include: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3 and / or InTe; ternary compounds such as InGaS3 and / or InGaSe3; and / or any combination thereof.
[0639] Non-limiting examples of Group I-III-VI semiconductor compounds may include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, and / or AgAlO2.
[0640] Non-limiting examples of Group IV-VI semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe and / or SnPbSTe; and / or any combination thereof.
[0641] The Group IV elements or compounds may include: simple substances, such as Si and / or Ge; binary compounds, such as SiC and / or SiGe; and / or any combination thereof.
[0642] Each element included in the multi-element compound (such as the binary compound, the ternary compound, and the quaternary compound) may be present in the particle at a substantially uniform concentration or a non-substantially uniform concentration.
[0643] In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or may have a core-shell dual structure. For example, the material included in the core and the material included in the shell may be different from each other.
[0644] The shell of a quantum dot can act as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or act as a charged layer to impart electrophoretic properties to the quantum dot. 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 toward the center of the core.
[0645] Examples of quantum dot shells may include metal oxides, metalloid oxides, or non-metal oxides, semiconductor compounds, and / or (e.g., any suitable) combinations thereof. Non-limiting examples of metal oxides, metalloid oxides, or non-metal oxides may include: binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4; and / or any combination thereof. Examples of semiconductor compounds may include: II-VI semiconductor compounds, as described herein; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; and / or any combination thereof. For example, semiconductor compounds suitable as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0646] The quantum dots may have an emission spectrum having a full width at half maximum (FWHM) of about 45 nm or less, about 40 nm or less, or, for example, about 30 nm or less. When the FWHM of the emission spectrum of the quantum dots is within these ranges, the quantum dots may have improved color purity or improved color reproducibility. In addition, because the light emitted by the quantum dots is emitted in all directions, a wide viewing angle may be improved.
[0647] Additionally, quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0648] Because the band gap of quantum dots can be adjusted by controlling the size of quantum dots, light with one or more suitable wavelengths can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths can be realized. For example, the size of the quantum dots can be selected so that the quantum dots can emit red light, green light, and / or blue light. In addition, quantum dots of appropriate size can be configured to emit white light by combining light of one or more suitable colors.
[0649] Electron transport region in the intermediate layer 130
[0650] The electron transport region may have: i) a single-layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material; ii) a single-layer structure including (e.g., consisting of) a single layer including multiple materials different from each other; or iii) a multilayer structure including multiple layers including multiple materials different from each other.
[0651] 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.
[0652] 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 of each structure are stacked sequentially from the emission layer in the order stated.
[0653] In one or more embodiments, the electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C1-C 60 Metal-free compounds of ring groups.
[0654] In one or more embodiments, the electron transport region may include a compound represented by Formula 601:
[0655] Formula 601
[0656] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0657] Wherein, in formula 601,
[0658] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group,
[0659] xe11 can be 1, 2 or 3,
[0660] xe1 can be 0, 1, 2, 3, 4, or 5,
[0661] R 601may be unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ),-C(=O)(Q 601 )、-S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0662] Q 601 To Q 603 can be the same as described in reference Q1,
[0663] xe21 can be 1, 2, 3, 4, or 5, and
[0664] Selected from Ar 601 , L 601 and R 601 At least one of them may be independently unsubstituted or substituted with at least one R 10a π-electron-poor nitrogen-containing C1-C 60 Cyclic group.
[0665] In one or more embodiments, if xe11 in equation 601 is 2 or greater (eg, when xe11 in equation 601 is 2 or greater), then the plurality of Ar 601 Two or more of may be linked to each other via a single bond.
[0666] In one or more embodiments, Ar in Formula 601 601 The anthracene group may be substituted or unsubstituted.
[0667] In one or more embodiments, the electron transport region may include a compound represented by Formula 601-1:
[0668] Formula 601-1
[0669]
[0670] Among them, in formula 601-1,
[0671] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and selected from X 614To X 616 At least one of may be N,
[0672] L 611 To L 613 Can be compared with reference L 601 Same as described,
[0673] xe611 to xe613 may all be the same as described with reference to xe1.
[0674] R 611 to R 613 Can be compared with reference R 601 Same as described, and
[0675] R 614 to R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group.
[0676] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.
[0677] In one or more embodiments, the electron transport region may include: at least one of Compound ET1 to Compound ET45 (e.g., selected from Compound ET1 to Compound ET45); 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP); 4,7-diphenyl-1,10-phenanthroline (Bphen); tris(8-hydroxyquinolinolato)aluminum (Alq3); bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq); 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ); 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ); or any combination thereof:
[0678]
[0679]
[0680]
[0681] The thickness of the electron transport region can 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 may 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 range described above, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.
[0682] In one or more embodiments, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material in addition to one or more of the materials described above.
[0683] 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, a 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, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0684] In one or more embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0685]
[0686] In one or more embodiments, the electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may directly contact the second electrode 150.
[0687] The electron injection layer can have: i) a single-layer structure including a single layer (e.g., consisting of a single layer), the single layer including a single type of material (e.g., consisting of a single type of material); ii) a single-layer structure including a single layer (e.g., consisting of a single layer), the single layer including multiple types of materials different from each other; or iii) a multi-layer structure including multiple layers, the multiple layers including multiple types of materials different from each other.
[0688] The electron injection layer can 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.
[0689] The alkali metal can include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal can include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal can include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0690] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound can 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.
[0691] The alkali metal compound can include: alkali metal oxides such as Li2O, Cs2O, and / or K2O; alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI; or any combination thereof. The alkaline earth metal compound can include alkaline earth metal compounds (e.g., 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-xO (where x is a real number satisfying 0 < x < 1). 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 Lu2Te3.
[0692] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include: i) one of the metal ions of an alkali metal, one of the metal ions of an alkaline earth metal, and one of the metal ions of a rare earth metal, respectively; and ii) ligands (e.g., 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) bound to the metal ion (e.g., the corresponding metal ion).
[0693] In one or more embodiments, the electron injection layer may include an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof as described above (e.g., composed of an alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, 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).
[0694] In one or more embodiments, the electron injection layer may include: i) an alkali metal compound (e.g., an alkali metal halide); or ii) a) an alkali metal compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof (e.g., consisting of i) an alkali metal compound (e.g., an alkali metal halide); or ii) a) an alkali metal compound (e.g., an alkali metal halide) and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof). In one or more embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and / or a LiF:Yb co-deposition layer, etc.
[0695] When the electron injection layer also includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the matrix including the organic material.
[0696] The thickness of the electron injection layer can be about to about (For example, about to about When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0697] Second electrode 150
[0698] The second electrode 150 may be disposed on the intermediate layer 130 having the structure described above. The second electrode 150 may be a cathode as an electron injection electrode, and may be formed using metals, alloys, conductive compounds, or any combination thereof each having a low work function.
[0699] 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 transflective electrode, or a reflective electrode.
[0700] The second electrode 150 may have a single-layer structure or a multi-layer structure including a plurality of layers.
[0701] Covering
[0702] The first cover layer may be disposed outside the first electrode 110 (e.g., on the first electrode 110), and / or the second cover layer may be disposed 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 cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150 are sequentially stacked in the stated order; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the stated order; or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are sequentially stacked in the stated order.
[0703] In one or more embodiments, light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be extracted toward the outside through the first electrode 110 (which is a transflective electrode or a transmissive electrode) and the first cover layer. In one or more embodiments, light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be extracted toward the outside through the second electrode 150 (which is a transflective electrode or a transmissive electrode) and the second cover layer.
[0704] According to the principle of constructive interference, the first and second covering layers can increase external emission efficiency. Therefore, the light extraction efficiency of the light emitting device 10 can be increased, so that the light emitting efficiency of the light emitting device 10 can be improved.
[0705] Each of the first and second cover layers may include a material having a refractive index of 1.6 or greater (eg, at 589 nm).
[0706] 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.
[0707] At least one of the first covering layer and the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphine 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 amine-containing compound may each optionally be substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first covering layer and the second covering layer may (for example, the first covering layer and the second covering layer may each independently) include an amine-containing compound.
[0708] In one or more embodiments, at least one of the first and second covering layers may (eg, the first and second covering layers may each independently) include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0709] In one or more embodiments, at least one of the first cover layer and the second cover layer may (for example, the first cover layer and the second cover layer may each independently) include at least one of compounds HT28 to HT33 (for example, selected from compounds HT28 to HT33); at least one of compounds CP1 to CP6 (for example, selected from compounds CP1 to CP6); β-NPB; or any combination thereof:
[0710]
[0711] membrane
[0712] The organometallic compound represented by Formula 1 may be included in one or more suitable films. Therefore, one or more aspects of the embodiments of the present disclosure relate to a film comprising an organometallic compound represented by Formula 1. The film may be, for example, an optical member (or light control element) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer and / or a quantum dot layer, etc.), a light blocking member (e.g., a light reflecting layer and / or a light absorbing layer, etc.), and / or a protective member (e.g., an insulating layer and / or a dielectric layer, etc.), etc.
[0713] electronic devices
[0714] The light emitting device may be included in one or more suitable electronic devices. For example, the electronic device including the light emitting device may be a lighting device and / or an authentication device.
[0715] In one or more embodiments, in addition to the light-emitting device, the electronic device (e.g., a light-emitting 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 arranged in at least one direction of travel of the light emitted from the light-emitting device. For example, in one or more embodiments, the light emitted from the light-emitting device may be blue light or white light (e.g., a combined white light). The details regarding the light-emitting device may be the same as described herein. In one or more embodiments, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.
[0716] 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 sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the sub-pixel regions.
[0717] A pixel defining film may be disposed between the sub-pixel regions to define each of the sub-pixel regions.
[0718] In one or more embodiments, the color filter may further include a plurality of color filter regions and light shielding patterns disposed between the color filter regions, and the color conversion layer may further include a plurality of color conversion regions and light shielding patterns disposed between the color conversion regions.
[0719] The plurality of color filter regions (or color conversion regions) may include a first region configured to emit a first color of light, a second region configured to emit a second color of light, and / or a third region configured to emit a third color of light, wherein the first color of light, the second color of light, and / or the third color of light may have different maximum emission wavelengths. In one or more embodiments, the first color of light may be red light, the second color of light may be green light, and the third color of light may be blue light. In one or more embodiments, the plurality of color filter regions (or color conversion regions) may include quantum dots. For example, 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) any quantum dots. Details regarding the quantum dots may be the same as described herein. Each of the first, second, and third regions may also include a scatterer.
[0720] In one or more embodiments, the light emitting device may emit a first light, the first region may absorb the first light to emit a first-first color light, the second region may absorb the first light to emit a second-first color light, and the third region may absorb the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0721] In one or more embodiments, in addition to the light-emitting device 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, wherein 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.
[0722] The thin film transistor may further include a gate electrode and / or a gate insulating film, etc.
[0723] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, and / or an oxide semiconductor, etc.
[0724] 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 arranged between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside while (for example, concurrently) preventing ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer comprising at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0725] In one or more embodiments, in addition to the color filter and / or color conversion layer, various functional layers may be disposed on the seal portion depending on the intended use of the electronic device. Non-limiting examples of the functional layers include a touch screen layer and a polarizing layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.
[0726] In addition to the light emitting device 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 (eg, fingertips and / or pupils, etc.).
[0727] The electronic device can be applied to one or more displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscope displays), fish finders, one or more suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), and / or projectors, etc.
[0728] Figure 2 and Figure 3 Description
[0729] Figure 2 is a cross-sectional view of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0730] Figure 2 The light emitting apparatus may include a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation part 300 sealing the light emitting device.
[0731] 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 impurities from penetrating the substrate 100 and may provide a flat surface on the substrate 100.
[0732] 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 .
[0733] 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.
[0734] 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 .
[0735] An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the electrodes from each other.
[0736] 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 arranged to contact the exposed portions of the source region and the drain region of the active layer 220, respectively.
[0737] The TFT may be electrically connected to the light-emitting device to drive the light-emitting device and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, and / or a combination thereof (e.g., any suitable). The light-emitting device may be disposed on the passivation layer 280. The light-emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0738] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be arranged to be connected to the exposed portion of the drain electrode 270.
[0739] A pixel defining film 290 including an insulating material may be on the first electrode 110. The pixel defining film 290 may expose a specific region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic-based organic film. Figure 2, but in one or more embodiments, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining film 290 to be arranged in the form of a common layer.
[0740] The second electrode 150 may be on the intermediate layer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0741] The encapsulation part 300 may be on the cover layer 170. The encapsulation part 300 may be arranged on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; organic films including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; and / or (e.g., any suitable) combination of inorganic and organic films.
[0742] Figure 3 is a cross-sectional view of a light emitting device as an example of an electronic device according to one or more embodiments of the present disclosure.
[0743] In addition to the light shielding pattern 500 and the functional region 400 being additionally arranged on the encapsulation portion 300, Figure 3 The light emitting device and Figure 2 The functional area 400 may be: i) a color filter area; ii) a color conversion area; or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, the functional area 400 may be: i) a color filter area; ii) a color conversion area; or iii) a combination of a color filter area and a color conversion area. Figure 3 The light-emitting devices in the light-emitting apparatus may be series-connected light-emitting devices.
[0744] Figure 4 Description
[0745] Figure 4is a schematic perspective view of an electronic equipment 1 including a light-emitting device according to one or more embodiments of the present disclosure. As an electronic device that displays moving images or still images, the electronic equipment 1 can be a portable electronic equipment (such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook, an e-book, a portable multimedia player (PMP), a navigation or ultra-mobile PC (UMPC)) and one or more suitable products (such as a TV, a laptop computer, a monitor, a billboard or an Internet of Things (IOT) device). The electronic equipment 1 can be such a product as above or a part thereof. In one or more embodiments, the electronic equipment 1 can be a wearable device (such as a smart watch, a watch phone, a glasses-type or glasses-like 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 equipment 1 may be a dashboard of a vehicle, a central information display (CID) arranged on a central dashboard or instrument panel of a vehicle, a room mirror display replacing a side mirror of a vehicle, an entertainment display for a rear seat of a vehicle or a display arranged behind a front seat thereof, or a head-up display (HUD) mounted in front of the vehicle or projected on a front windshield, or a computer-generated holographic augmented reality head-up display (CGHAR HUD). For ease of explanation, Figure 4 An embodiment is shown in which the electronic equipment 1 is a smartphone.
[0746] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device of the electronic equipment 1 may realize an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.
[0747] The non-display area NDA is an area where no image is displayed and may be entirely around the display area DA (e.g., surrounding the display area DA). A driver for supplying electrical signals or power to the display device arranged in the display area DA may be arranged in the non-display area NDA. Pads (also called "pads" or "solder pads"), which are areas to which electronic components or printed circuit boards can be electrically connected, may be arranged in the non-display area NDA.
[0748] In the electronic equipment 1, the length in the x-axis direction (or x direction) and the length (eg, width) in the y-axis direction (or y direction) may be different from each other. In one or more embodiments, as Figure 4 As shown in , the length in the x-axis direction may be shorter than the length in the y-axis direction (e.g., 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., width). In one or more embodiments, the length in the x-axis direction may be longer than the length in the y-axis direction (e.g., width).
[0749] Figure 5 and Figures 6A to 6C Description
[0750] Figure 5 is a schematic diagram of the exterior of a vehicle 1000 as electronic equipment including a light emitting device according to one or more embodiments. Figures 6A to 6C 1 and 2 are schematic diagrams of the interior of a vehicle 1000 according to one or more embodiments.
[0751] Reference 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, object, or animal) from a starting point to a destination. The vehicle 1000 may include a vehicle that travels on roads or tracks, a ship that moves on the ocean or river, and / or an airplane that flies in the sky using the action of air.
[0752] In one or more embodiments, the vehicle 1000 can travel on a road or track. The vehicle 1000 can move in a predetermined direction based on the rotation of at least one of its wheels. In one or more embodiments, the vehicle 1000 can include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train running on a track.
[0753] Vehicle 1000 may include a body having an interior and an exterior, and a chassis in which mechanical devices required for driving are mounted as other components in addition to the body. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and / or pillars provided at the boundaries between doors. The chassis of vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel system, front and rear wheels, and / or left and right wheels, etc.
[0754] The vehicle 1000 may include side window glasses 1100 , a front window glass 1200 , side view mirrors 1300 , a cluster 1400 , a central instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0755] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0756] A side window glass 1100 may be mounted on the side of the vehicle 1000. In one or more embodiments, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided, and the plurality of side window glasses 1100 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 positioned adjacent to the cluster 1400. The second side window glass 1120 may be positioned adjacent to the passenger seat instrument panel 1600.
[0757] In one or more embodiments, the side window glass 1100 can be spaced apart and / or separated from each other in the x-direction or the -x-direction (the direction opposite to the x-direction). In one or more embodiments, the first side window glass 1110 and the second side window glass 1120 can be spaced apart and / or separated from each other (e.g., spaced apart or separated) in the x-direction or the -x-direction. For example, the imaginary straight line L connecting the side window glass 1100 can extend in the x-direction or the -x-direction. In one or more embodiments, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 can extend in the x-direction or the -x-direction.
[0758] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 that are opposite to (eg, facing) each other.
[0759] Side-view mirror 1300 can provide a rear view of vehicle 1000. Side-view mirror 1300 can be mounted on the exterior of the vehicle body. In one or more embodiments, multiple side-view mirrors 1300 can be provided. Any one of multiple side-view mirrors 1300 can be positioned outside first side window glass 1110. Another one of multiple side-view mirrors 1300 can be positioned outside second side window glass 1120.
[0760] Cluster 1400 may be arranged in front of the steering wheel. Cluster 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, turn indicators, a high beam indicator, warning lights, a seat belt warning light, an odometer, a tachograph, an automatic shift selector indicator, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0761] The central instrument panel 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 arranged. The central instrument panel 1500 may be arranged at one side of the cluster 1400 .
[0762] Passenger-seat instrument panel 1600 may be separate and / or separated (e.g., spaced apart or separated) from cluster 1400, with center instrument panel 1500 disposed between passenger-seat instrument panel 1600 and cluster 1400. In one or more embodiments, cluster 1400 may be disposed corresponding to a driver's seat, and passenger-seat instrument panel 1600 may be disposed corresponding to a passenger seat. In one or more embodiments, cluster 1400 may be adjacent to first side window glass 1110, and passenger-seat instrument panel 1600 may be adjacent to second side window glass 1120.
[0763] 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 side windows 1100 that are opposed to (e.g., facing) each other. The display device 2 may be disposed on at least one of the cluster 1400, the center instrument panel 1500, and the passenger seat instrument panel 1600.
[0764] The display device 2 may include an organic light-emitting display device, an inorganic light-emitting display device, and / or a quantum dot display device, etc. Hereinafter, as the display device 2 according to one or more embodiments, an organic light-emitting display device including a light-emitting device according to the disclosure will be described as an example, but one or more suitable types (kinds) of display devices as described above may be used in the embodiments.
[0765] Reference Figure 6A In one or more embodiments, the display device 2 may be disposed on the central instrument panel 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 related to vehicle settings.
[0766] Reference Figure 6B In one or more embodiments, display device 2 may be disposed on cluster 1400. In these embodiments, cluster 1400 may display driving information and the like via display device 2. For example, cluster 1400 may be implemented digitally. A digitally operated cluster 1400 may display vehicle and driving information as images. In one or more embodiments, a tachometer needle and range, as well as one or more suitable warning light icons, may be displayed via digital signals.
[0767] Reference Figure 6CIn one or more embodiments, the display device 2 may be disposed on a passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or disposed on the passenger seat instrument panel 1600. In one or more embodiments, the display device 2 disposed on the passenger seat instrument panel 1600 may display images related to the information displayed on the cluster 1400 and / or the information displayed on the center instrument panel 1500. In one or more embodiments, the display device 2 disposed on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster 1400 and / or the information displayed on the center instrument panel 1500.
[0768] Manufacturing method
[0769] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a specific region by using one or more suitable methods (such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing and / or laser induced thermal imaging, etc.).
[0770] 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, the deposition temperature may be in the range of about 100° C. to about 500° C. ... -8 About 10 -3 The vacuum degree is within the range of Torr and is about to about The vacuum deposition is performed at a deposition rate within a range of .
[0771] Definition of terms
[0772] As used herein, the term "C3-C 60 "Carbocyclyl" refers to a cyclic group that includes only carbon as a ring-forming atom (e.g., consists of only carbon as a ring-forming atom) and has 3 to 60 carbon atoms, and the term "C1-C 60 The term "heterocyclic group" refers to a ring group having 1 to 60 carbon atoms and having a heteroatom as a ring-forming atom in addition to carbon. 60 Carbocyclic and C1-C 60 The heterocyclic groups may be monocyclic groups (e.g., monocyclic groups consisting of one (e.g., exactly one) ring) or polycyclic groups in which two or more rings are condensed with each other. 60 The number of ring-forming atoms of the heterocyclic group can be 3 to 61.
[0773] As used herein, the term "cyclic group" may (for example, simultaneously) include C3-C60 Carbocyclic and C1-C 60 Both heterocyclic groups.
[0774] 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 part, and the term "π-electron-poor nitrogen-containing C1-C 60 The term "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming portion.
[0775] For example,
[0776] C3-C 60 The carbocyclic group may be: i) a group T1; or ii) a condensed ring group in which two or more of the group T1 are condensed with each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a phenanthren group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, perylene group, pentaphene group, heptalene group, tetracene group, phenene group, hexacenyl group, pentacene group, rubride group, coronene group, ovophenyl group, indene group, fluorene group, spirobifluorene group, benzofluorene group, indenophenanthrene group or indenoanthracene group),
[0777] C1-C 60The heterocyclic group may be: i) a group T2; ii) a condensed ring group in which two or more of the groups T2 are condensed with each other; or iii) a condensed ring group in which at least one group T2 and at least one group T1 are condensed with each other (e.g., a pyrrole group, a thiophene group, a furan group, an indole group, a benzindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolecarbazole group, benzofuranocarbazole group, benzothiophenocarbazole group, benzosiloleocarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofuranodibenzofuran group, benzofuranodibenzo Thiophene group, benzothienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzo quinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group and / or azadibenzofuran group, etc.),
[0778] π-electron-rich C3-C 60 The cyclic group may be: i) a group T1; ii) a condensed ring group in which two or more of the groups T1 are condensed with each other; iii) a group T3; iv) a condensed ring group in which two or more of the groups T3 are condensed with each other; or v) a condensed ring group in which at least one group T3 and at least one group T1 are condensed with each other (e.g., C3-C 60a carbocyclic group, a 1H-pyrrole group, a thiole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothienocarbazole group, a benzothioleocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group and / or a benzothienodibenzothiophene group, etc.),
[0779] π-electron-poor nitrogen-containing C1-C 60 The cyclic group may be: i) a group T4; ii) a condensed ring group in which two or more of the groups T4 are condensed with each other; iii) a condensed ring group in which at least one group T4 and at least one group T1 are condensed with each other; iv) a condensed ring group in which at least one group T4 and at least one group T3 are condensed with each other; or v) a condensed ring group in which at least one group T4, at least one group T1, and at least one group T3 are condensed with each other (e.g., a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group and / or an azadibenzofuran group, etc.),
[0780] The group T1 can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,
[0781] The group T2 can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borolide group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,
[0782] The group T3 may be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group or a borole group, and
[0783] The group T4 can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
[0784] As used herein, the terms "cyclic group", "C3-C 60 Carbocyclic group", "C1-C 60 Heterocyclic group", "π-electron-rich C3-C 60 "Cyclic" or "π-electron-poor nitrogen-containing C1-C 60 The term "cyclic group" refers to a group condensed to any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, and / or a tetravalent group, etc.) according to the structure of the formula used for the corresponding term. For example, a "phenyl group" may be a benzo group, a phenyl group, and / or a phenylene group, etc., which can be easily understood by those skilled in the art based on the structure of the formula including the "phenyl group".
[0785] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Non-limiting examples of heterocyclic groups may include 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 condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. 60 Carbocyclic groups and divalent C1-C 60Non-limiting examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocycloalkylene, C3-C 10 Cycloalkenylene, C1-C 10 Heterocycloalkenylene, C6-C 60 Arylene, C1-C 60 heteroarylene groups, divalent non-aromatic condensed polycyclic groups and divalent non-aromatic condensed heteropolycyclic groups.
[0786] As used herein, the term "C1-C 60 The term “alkyl” refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, 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 tert-decyl. As used herein, the term “C1-C 60 "Alkylene" refers to a group having a C1-C 60 Alkyl groups are divalent groups of substantially the same structure.
[0787] As used herein, the term "C2-C 60 "Alkenyl" refers to a C2-C 60 The term "C2-C4" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the alkyl group, and non-limiting examples thereof may include ethenyl, propenyl, and butenyl. 60 "Alkenylene" refers to a group having a C2-C 60 Alkenyl is a divalent group of substantially the same structure.
[0788] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 The term "C2-C4" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, and non-limiting examples thereof may include ethynyl and propynyl. 60 "Alkyne" refers to a group having a C2-C 60 Alkynyl is a divalent group of substantially the same structure.
[0789] As used herein, the term "C1-C 60 "Alkoxy" refers to 101 (Among them, A 101 It is C1-C 60The monovalent group represented by an alkyl group is a methoxy group, an ethoxy group, and an isopropoxy group.
[0790] As used herein, the term "C3-C 10 The term "cycloalkyl" refers to a monovalent saturated hydrocarbon ring 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 bicyclo[2.2.2]octyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a group having a C3-C 10 Cycloalkyl is a divalent group of substantially the same structure.
[0791] As used herein, the term "C1-C 10 The term "heterocycloalkyl" as used herein refers to a monovalent cyclic group of 1 to 10 carbon atoms which includes 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-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl. 10 "Heterocycloalkylene" refers to a group having a C1-C 10 Heterocycloalkyl is a divalent group of substantially the same structure.
[0792] As used herein, the term "C3-C 10 The term "C3-C4-alkenyl" as used herein refers to a monovalent cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond and no aromaticity in its ring, and non-limiting examples thereof may include cyclopentenyl, cyclohexenyl and cycloheptenyl. 10 "Cycloalkenylene" refers to a group having a C3-C 10 Cycloalkenyl is a divalent group of substantially the same structure.
[0793] As used herein, the term "C1-C 10 "Heterocycloalkenyl" refers to a monovalent cyclic group of 1 to 10 carbon atoms that includes at least one heteroatom as a ring atom in addition to carbon atoms in its ring structure and includes at least one double bond (e.g., carbon-carbon double bond). 10 Non-limiting examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkenylene" refers to a 10 Heterocycloalkenyl is a divalent group of substantially the same structure.
[0794] As used herein, the term "C6-C 60"Aryl" refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C6-C 60 "Arylene" refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 60 Non-limiting examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, coryl and oxadiphenyl. 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the two or more rings may be condensed with each other.
[0795] 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 including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 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 including at least one heteroatom as a ring atom in addition to carbon atoms. 60 Non-limiting examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, and naphthyridinyl. 60 Heteroaryl and C1-C 60 When the heteroarylene group includes two or more rings, the two or more rings may be condensed with each other.
[0796] As used herein, term " monovalent non-aromatic condensation polycyclic radical " refers to two or more rings, only carbon atoms (for example, having 8 to 60 carbon atoms) that are condensed with each other and as a whole, a monovalent group without aromaticity in the whole molecular structure. The non-limiting example of monovalent non-aromatic condensation polycyclic radical can include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl and indenoanthryl. As used herein, term " divalent non-aromatic condensation polycyclic radical " refers to a divalent group with substantially the same structure as the monovalent non-aromatic condensation polycyclic radical.
[0797] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group having two or more rings condensed with each other, including at least one heteroatom as a ring-constituting atom in addition to carbon atoms (for example, having 1 to 60 carbon atoms), and having non-aromaticity in its entire molecular structure as a whole. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group may include pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiorolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiorolyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothiorolyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazole ... The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
[0798] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 It is C6-C 60 aryl), and as used herein the term "C6-C 60 "Arylthio" refers to -SA 103 (Among them, A 103 It is C6-C 60 aryl).
[0799] As used herein, the term "C7-C 60 "Arylalkyl" refers to -A 104 A 105 (Among them, A 104 It is C1-C 54 Alkylene, and A 105 It is C6-C 59 aryl), and as used herein the term "C2-C 60 "Heteroarylalkyl" refers to -A 106 A 107 (Among them, A 106 It is C1-C59 Alkylene, and A 107 It is C1-C 59 heteroaryl).
[0800] As used herein, the term "R 10a "refer to:
[0801] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;
[0802] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 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 C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy;
[0803] Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 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 )(Q23 ),-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 C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl; or
[0804] -Si(Q 31 )(Q 32 )(Q 33 ),-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0805] As used herein, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 The alkyl radicals may be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C2-1-2-1-3-1-4-1-1, which are unsubstituted or substituted with deuterium, -F, cyano, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof. 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60C3-C6 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl.
[0806] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Non-limiting examples of heteroatoms may include B, O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0807] As used herein, "Ph" refers to phenyl, as used herein, "Me" refers to methyl, as used herein, "Et" refers to ethyl, as used herein, "tert-Bu" or "Bu" refers to ethyl. t ” refers to a tert-butyl group, and “OMe” as used herein refers to a methoxy group.
[0808] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". For example, a "biphenyl group" may be a group having C6-C 60 A phenyl group substituted with an aryl group as a substituent.
[0809] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted with a C6-C 60 C6-C 60 A phenyl group substituted with an aryl group as a substituent.
[0810] Unless otherwise defined, * and *' as used herein refer to the binding sites to adjacent atoms in the corresponding formula or moiety.
[0811] Hereinafter, the compound according to one or more embodiments and the light-emitting device according to one or more embodiments will be described in more detail with reference to 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 the same molar equivalent of A.
[0812] Example
[0813] Synthesis Example 1: Synthesis of Compound 13
[0814]
[0815] 1) Synthesis of Intermediate 13-1
[0816] 6-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 (1.0 equivalent), bis(diphenylphosphino)ferrocenepalladium dichloride ((Pd(dppf))Cl2) (0.05 equivalent), bis(pinacolato)diboron (B2pin2) (1.5 equivalents) and potassium acetate (3 equivalents) were dissolved in 1,4-dioxane and then stirred at 100°C for 24 hours to obtain a reaction product. The reaction product was cooled at room temperature, the solvent was removed therefrom by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by performing three extraction processes therefrom using dichloromethane (MC) and water. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (dichloromethane / hexane (MC / Hex) as an eluent) to obtain intermediate 13-1 (yield 82%).
[0817] 2) Synthesis of Intermediate 13-2
[0818] Intermediate 13-1 (1.0 equivalent), 3-bromo-5-(tert-butyl)-[1,1':3',1"-terphenyl]-2',4',5',6'-d4-2-amine (1.0 equivalent), [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]chloro[3-phenylpropenyl]palladium(II) (CX31 Umicore) (0.05 equivalent) and potassium carbonate (2.5 equivalent) were dissolved in 1,4-dioxane:H2O (3:1), and then stirred at 100°C for 24 hours to obtain a reaction product. The reaction product was cooled at room temperature, the solvent was removed therefrom by distillation under a reduced pressure of 8 mbar, and an extraction process was performed thereon three times by using MC and water to obtain an organic layer. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (MC / Hex as an eluent) to obtain Intermediate 13-2 (yield 71%).
[0819] 3) Synthesis of Intermediate 13-3
[0820] Intermediate 13-2 (1.0 equivalent), 1-bromo-2-nitrobenzene (2 equivalents), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (Sphos, 0.10 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.05 equivalents) and sodium tert-butoxide (NaOtBu, 3 equivalents) were dissolved in toluene and then stirred at 110°C for 24 hours to obtain a reaction product. The reaction product was cooled at room temperature, the solvent was removed therefrom by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by performing an extraction process thereon three times using MC and water. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (MC / Hex as an eluent) to obtain Intermediate 13-3 (yield 90%).
[0821] 4) Synthesis of Intermediate 13-4
[0822] Intermediate 13-3 (1.0 equivalent) and tin (5 equivalents) were dissolved in ethanol (EtOH) and stirred. After hydrogen chloride (12M) was injected therein, the resulting reaction product was stirred at 80°C for 6 hours. The reaction product was cooled at room temperature, the solvent was removed therefrom by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by performing three extraction processes on it using MC and water. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (MC / Hex as eluent) to obtain intermediate 13-4 (yield 89%).
[0823] 5) Synthesis of Intermediate 13-5
[0824] Intermediate 13-4 (1.0 equivalent), 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 (1.0 equivalent), Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0), 0.05 equivalent), Xphos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 0.10 equivalent) and sodium tert-butoxide (2.0 equivalent) were dissolved in toluene (0.1M), and then stirred at 110°C for 2 hours to obtain a reaction product. The reaction product was cooled at room temperature, the solvent was removed therefrom by distillation under a reduced pressure of 8 mbar, and an organic layer was obtained by performing an extraction process thereon three times using MC and water. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (MC: hexane as an eluent) to obtain Intermediate 13-5 (yield 78%).
[0825] 6) Synthesis of Intermediate 13-6
[0826] Intermediate 13-5 (1.0 equivalent) was dissolved in triethyl orthoformate (30 equivalents), and 37% HCl (1.5 equivalents) was added thereto. The mixed solution was then stirred at 80°C for 24 hours to obtain a reaction product. The reaction product was cooled at room temperature, concentrated and triethyl orthoformate was removed, and three extraction processes were performed on it using MC and water to obtain an organic layer. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (MC: methanol as eluent) to obtain intermediate 13-6 (yield 89%).
[0827] 7) Synthesis of Compound 13
[0828] Intermediate 13-6 (1.0 equivalents), potassium chloroplatinite (II) acid (1.1 equivalents) and 2,6-lutidine (4.0 equivalents) were dissolved in 1,2-dichlorobenzene (o-DCB) (0.05M), and then stirred at 120 ° C for 18 hours under nitrogen conditions to obtain a reaction product. The reaction product was cooled at room temperature, concentrated and 1,2-dichlorobenzene was removed, and three extraction processes were performed on it using dichloromethane and water to obtain an organic layer. The organic layer thus obtained was dried over anhydrous magnesium sulfate, concentrated, and then subjected to column chromatography (MC: hexane as eluent) to synthesize compound 13 (yield 48%).
[0829] Electrospray ionization-liquid chromatography-mass spectrometry (ESI-LCMS): [M] + :C 70 H 53 D 11 N4OPt,1183.1
[0830] Synthesis Example 2: Synthesis of Compound 18
[0831]
[0832] Synthesis of compound 18
[0833] Compound 18 (yield 47%) was synthesized in essentially the same manner as Intermediate 13-1 to Intermediate 13-6 and Compound 13, except that 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 and 3-bromo-5,5'-di-tert-butyl-[1,1':3',1"-terphenyl]-2',4',6'-d3-2-amine was used instead of 3-bromo-5-(tert-butyl)-[1,1':3',1"-terphenyl]-2',4',5',6'-d4-2-amine.
[0834] ESI-LCMS: [M] + :C 74 H 46 D 26 N4OPt,1255.0
[0835] Synthesis Example 3: Synthesis of Compound 76
[0836]
[0837] Synthesis of compound 76
[0838] Compound 76 (yield 54%) was synthesized in essentially the same manner as Intermediate 13-1 to Intermediate 13-6 and Compound 13, except that 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 and 3-bromo-2",4",5-tri-tert-butyl-[1,1':4',1"-terphenyl]-2',3',5',6'-d4-2-amine was used instead of 3-bromo-5-(tert-butyl)-[1,1':3',1"-terphenyl]-2',4',5',6'-d4-2-amine.
[0839] ESI-LCMS: [M] + :C 78 H 56 D 24 N4OPt,1309.2
[0840] Synthesis Example 4: Synthesis of Compound 111
[0841]
[0842] Synthesis of compound 111
[0843] Compound 111 (yield 57%) was synthesized in essentially the same manner as Intermediate 13-1 to Intermediate 13-6 and Compound 13, except that 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 and 3-bromo-3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-amine was used instead of 3-bromo-5-(tert-butyl)-[1,1':3',1"-terphenyl]-2',4',5',6'-d4-2-amine.
[0844] ESI-LCMS: [M] + :C 72 H 53 D 23 N4OPt,1232.1
[0845] Synthesis Example 5: Synthesis of Compound 207
[0846]
[0847] Synthesis of compound 207
[0848] In addition, 6-bromo-1,1,4,4-tetrakis(methyl-d3)-1,2,3,4-tetrahydronaphthalene-2,2,3,3-d4 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3, and 3-bromo-4',5-di-tert-butyl-[1,1'-biphenyl]-2',3',5',6'-d4-2-amine was used instead of 3-bromo-5-(tert-butyl)-[1,1':3',1"-terphenyl]-2',4',5 ',6'-d4-2-amine, and using 2-(3-bromophenoxy)-9-(4-(tert-butyl)-5-(phenyl-d5)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4, compound 207 (yield 61%) was synthesized in essentially the same manner as the synthesis of intermediates 13-1 to intermediate 13-6 and compound 13.
[0849] ESI-LCMS: [M] + :C 74 H 43 D 29 N4OPt,1258.1
[0850] Synthesis Example 6: Synthesis of Compound 257
[0851]
[0852] Synthesis of compound 257
[0853] Compound 257 (yield 58%) was synthesized in essentially the same manner as Intermediate 13-1 to Intermediate 13-6 and Compound 13, except that 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 and 2-(3-bromophenoxy)-9-(4-(tert-butyl)-5-(phenyl-d5)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4 was used instead of 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d4.
[0854] ESI-LCMS: [M] + :C 76 H 36 D 32 N4OPt, 1281.2
[0855] Table 2
[0856]
[0857]
[0858] Example 1
[0859] As the anode, a 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.7 mm, and ultrasonically treated with isopropyl alcohol and (then) pure water for 5 minutes each, and then cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes. The obtained ITO glass substrate was then loaded on a vacuum deposition device.
[0860] The compound 2-TNATA used in the art is vacuum deposited on the substrate to form A hole injection layer having a thickness of 1000 nm was formed, and then 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum deposited thereon as a hole transport compound to form a hole injection layer having a thickness of 1000 nm. The hole transport layer has a thickness of .
[0861] Compound 13 (first compound), ETH85 (second compound), HTH53 (third compound) and DFD13 (fourth compound) in the blue fluorescent emission layer are simultaneously (e.g., concurrently) deposited on the hole transport layer to form a blue fluorescent emission layer having In this regard, based on 100 wt % of the total weight of the emission layer, the amount of compound 13 was 13 wt %, the amount of DFD13 was 1.5 wt %, and the weight ratio of ETH85 to HTH53 was 3.5:6.5.
[0862] Then, HBL-1 was vacuum deposited thereon to form a A hole blocking layer of a thickness of 1000 nm was formed, and CNNPTRZ and LiQ were deposited on the hole blocking layer in a weight ratio of 4:6 to form a Yb is deposited on the electron transport layer to form an electron transport layer having a thickness of An electron injection layer with a thickness of 1000 nm was formed, and Mg was vacuum-deposited thereon to form an electron injection layer having a thickness of 1000 nm. A cathode with a thickness of is formed, thereby completing the manufacture of the light-emitting device.
[0863]
[0864] Examples 2 to 12 and Comparative Examples 1 to 8
[0865] A light-emitting device was manufactured in substantially the same manner as in Example 1, except that the first to fourth compounds were changed when forming the emission layer as shown in Tables 3 and 4. In Tables 3 and 4, the amounts of the first and fourth compounds are expressed based on 100 wt% of the total weight of the emission layer.
[0866] Table 3
[0867]
[0868]
[0869] Table 4
[0870]
[0871]
[0872]
[0873]
[0874] Evaluation Example 2
[0875] The driving voltage (V), color coordinates CIE (y), color conversion efficiency (cd / A / y), emission color and lifetime (T) of the light emitting devices according to Examples 1 to 12 and Comparative Examples 1 to 8 were measured using a Keithley SMU 236 and a luminance meter PR650. 95 ), and the results are shown in Tables 5 and 6.
[0876] In Tables 5 and 6, at 10 mA / cm 2 The driving voltage and color conversion efficiency were measured at a current density of 100 nm and the lifetime (T 95 ) is measured until the luminance reaches 1000cd / m 2 The lifespan is shown as a relative value relative to that of Comparative Example 3 in Table 5, and as a relative value relative to that of Comparative Example 7 in Table 6.
[0877] Table 5
[0878]
[0879]
[0880] Table 6
[0881]
[0882] Referring to Table 5 and Table 6, it was confirmed that the light emitting devices of Examples 1 to 12 all had low driving voltage, high color conversion efficiency, and long life characteristics compared to Comparative Examples 1 to 8.
[0883] Referring to Table 5, it was confirmed that each of the light emitting devices of Examples 1 to 6 had similar or low driving voltage, high color conversion efficiency, and improved lifespan compared to the light emitting devices of Comparative Examples 1 to 4.
[0884] Referring to Table 6, it was confirmed that each of the light emitting devices of Examples 7 to 12 had similar or low driving voltage, high color conversion efficiency, and improved lifespan compared to the light emitting devices of Comparative Examples 5 to 8.
[0885] According to one or more embodiments of the present disclosure, the use of the organometallic compound of the present disclosure may enable the manufacture of a light emitting device having high efficiency and long lifetime, and a high-quality electronic device including the light emitting device.
[0886] In the present disclosure, it will be understood that the terms "including / variants thereof", "comprising / variants thereof" or "having / variants thereof" indicate the presence of stated 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.
[0887] In the context of this application, unless defined otherwise, the term "use" and variations thereof may be considered synonymous with the term "utilize" and variations thereof, respectively.
[0888] Throughout this disclosure, when a component (such as a layer, film, region, or plate) is referred to as being placed "on" another component, it will be understood that the component can be directly on the other component or another component can be placed therebetween. In some embodiments, "directly on" can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and another part. For example, "directly on" can mean that two layers or two components are disposed without utilizing an additional component, such as an adhesive component, therebetween.
[0889] 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.
[0890] As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."
[0891] As used herein, the terms "substantially," "approximately," or similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent deviations in measured or calculated values that one of ordinary skill in the art would recognize. Taking into account the measurements in question and the errors associated with the measurement of a particular quantity (i.e., the limitations of the measurement system), as used herein, "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art. For example, "approximately" can mean within one or more standard deviations, or within ±30%, ±20%, ±10%, ±5% of the stated value.
[0892] Any numerical range stated herein is intended to include all subranges of the same numerical precision contained within the stated range. For example, the range of "1.0 to 10.0" is intended to include all subranges between the stated minimum value of 1.0 and the stated maximum value of 10.0 (and including the stated minimum value of 1.0 and the stated 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 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all smaller numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all larger numerical limits contained therein. Therefore, the applicant reserves the right to amend the disclosure, including the claims, to explicitly state any subranges contained within the range explicitly stated herein.
[0893] According to the embodiments of the present disclosure described herein, the light-emitting device, light-emitting device, display device, electronic device, electronic device or any other related device or component can be implemented using any suitable hardware, firmware (e.g., an application-specific integrated circuit), software or a combination of software, firmware and hardware. For example, the various components of the device can be formed on an integrated circuit (IC) chip or on separate IC chips. In addition, the various components of the device can be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be processes or threads that execute computer program instructions and interact with other system components to perform the various functions described herein on one or more processors in one or more computing devices. The computer program instructions are stored in a memory that can be implemented in a computing device using a standard memory device (such as, for example, a random access memory (RAM)). The computer program instructions can also be stored in other non-transitory computer-readable media (such as, for example, a CD-ROM, a flash drive, etc.). In addition, it should be appreciated by those skilled in the art that, without departing from the scope of the embodiments of the present disclosure, the functions of various computing devices can be combined or integrated into a single computing device, or the functions of a particular computing device can be distributed across one or more other computing devices.
[0894] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. The description of features or aspects within each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that one or more suitable changes in form and details may be made therein without departing from the spirit and scope as defined by the appended claims and their equivalents.
Claims
1. A light-emitting device, comprising: a first electrode; a second electrode, opposite to the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and An organometallic compound represented by Formula 1: Formula 1 Formula 2 Among them, in formula 1 and formula 2, M1 is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, X1 to X4 are independently C or N, Ring CY1 to Ring CY4 are independently C5-C 30 Carbocyclic or C1-C 30 heterocyclic group, Ring CY5 is C3-C 10 Cycloalkyl, L1 to L3 are 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 )-*', * and *' all represent the binding sites with adjacent atoms, n1 to n3 are each independently an integer from 1 to 3, R 10 is a group represented by formula 2, R1 to R4, Z1 to Z5, R 1a and R 1b are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a 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), At least one selected from Z2 to Z4 is not hydrogen, Two or more selected from a plurality of R1 are optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, Two or more selected from a plurality of R2 are optionally combined with each other to form an unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, Two or more selected from a plurality of R3 are optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, Two or more selected from a plurality of R4 are optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, a1 to a4 are each independently an integer from 1 to 10, b1 is an integer from 1 to 20, b5 is an integer from 1 to 5, * indicates the binding site with the adjacent atom, and R 10a yes: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 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 C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 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 C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl; 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 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C2-1 ... 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C6 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl.
2. The light emitting device according to claim 1, wherein The first electrode is an anode, The second electrode is a cathode, The intermediate layer further includes a hole transport region between the first electrode and the emissive layer and an electron transport region between the emissive 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, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
3. The light emitting device according to claim 1, wherein The emission layer includes the organometallic compound represented by Formula 1. The light emitting device according to claim 1 , wherein: The intermediate layer includes: i) a first compound, which is the organometallic compound represented by Formula 1; and ii) a second compound comprising at least one π-electron-poor nitrogen-containing C1-C 60 Cyclic group; third compound, including π-electron-rich C3-C 60 a cyclic group or a pyridine group; a fourth compound capable of 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, and Compound CBP and Compound mCBP are excluded from the third compound: The light emitting device according to claim 4 , wherein: The intermediate layer includes: the first compound; and at least one of the second compound and the third compound. The light emitting device according to claim 5 , wherein: The intermediate layer further includes the fourth compound, which is a compound including at least one cyclic group including both boron and nitrogen as ring-constituting atoms. 7 . An electronic device comprising the light emitting device according to claim 1 .
8. The electronic device according to claim 7, further comprising a thin film transistor, in, 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.
9. An organometallic compound, said organometallic compound being represented by Formula 1: Formula 1 Formula 2 in, In Equation 1 and Equation 2, M1 is platinum, palladium, copper, silver, gold, rhodium, ruthenium, osmium, titanium, zirconium, hafnium, europium, terbium or thulium, Ring CY1 to Ring CY4 are independently C5-C 30 Carbocyclic or C1-C 30 heterocyclic group, Ring CY5 is C3-C 10 Cycloalkyl, X1 to X4 are independently C or N, L1 to L3 are 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 )-*', * and *' all represent the binding sites with adjacent atoms, n1 to n3 are each independently an integer from 1 to 3, R 10 is a group represented by formula 2, R1 to R4, Z1 to Z5, R 1a and R 1b are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a 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), At least one selected from Z2 to Z4 is not hydrogen, Two or more selected from a plurality of R1 are optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, Two or more selected from a plurality of R2 are optionally combined with each other to form an unsubstituted or substituted with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, Two or more selected from a plurality of R3 are optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, Two or more selected from a plurality of R4 are optionally combined with each other to form an unsubstituted or substituted group with at least one R 10a C3-C 60 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a C1-C 60 heterocyclic group, a1 to a4 are each independently an integer from 1 to 10, b1 is an integer from 1 to 20, b5 is an integer from 1 to 5, * indicates the binding site with the adjacent atom, and R 10a yes: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, or nitro; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 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 C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 alkoxy; Unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 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 C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 heteroarylalkyl; 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 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C2-1 ... 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl or C1-C 60 Alkoxy; or unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C3-C6 alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof 60 Carbocyclic group, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl or C2-C 60 Heteroarylalkyl.
10. The organometallic compound according to claim 9, wherein The organometallic compound has a twist angle ranging from 28 degrees to 42 degrees.
11. The organometallic compound according to claim 9, wherein Ring CY1 to ring CY4 are independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzogermanol group, dibenzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzothiophene ... benzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene-5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiorrole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, Azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group , quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group or 5,6,7,8-tetrahydroquinoline group.
12. The organometallic compound according to claim 9, wherein In formula 1, The moiety represented by is a group represented by any one selected from the group consisting of formula CY(1)-1 to formula CY(1)-12: In formula CY(1)-1 to formula CY(1)-12, R 10 As defined in Formula 1 and Formula 2, R 11 to R 13 are independently the same as defined in reference to R1 in Formula 1, c10 is an integer from 1 to 4, c11 is an integer from 1 to 3, c12 is 1 or 2, and * and *' both indicate the binding sites with adjacent atoms.
13. The organometallic compound according to claim 9, wherein In formula 1, The moiety represented by is a group represented by any one selected from the group consisting of formula CY(3)-1 to formula CY(3)-7: In formula CY(3)-1 to formula CY(3)-7, R3 is the same as defined in Formula 1, c31 is an integer from 1 to 6, c32 is an integer from 1 to 5, and *, *' and *" all indicate the binding sites with adjacent atoms.
14. The organometallic compound according to claim 9, wherein In formula 1, The moiety represented by is a group represented by any one selected from the group consisting of formula CY(4)-1 to formula CY(4)-16: In formula CY(4)-1 to formula CY(4)-16, R 41 to R 44 are independently the same as those defined in R4 in Formula 1, wherein R 41 to R 44 are not hydrogen, and * and *' both indicate the binding sites with adjacent atoms.
15. The organometallic compound according to claim 9, wherein R 10 is a group represented by any one selected from Formula 2-1 to Formula 2-4: In formula 2-1 to formula 2-4, Z1 to Z5 and b5 are the same as defined in Formula 2, Z 11 to Z 18 are independently: deuterium; or C1-C 10 alkyl, b11 is an integer from 1 to 7, b12 is an integer from 1 to 5, and * indicates the binding site with the adjacent atom.
16. The organometallic compound according to claim 9, wherein R 10 is a group represented by any one selected from Formula 2A-1 to Formula 2A-16: In Formula 2A-1 to Formula 2A-16, Z2 to Z5 and b5 are the same as defined in Formula 2, and * indicates the binding site with the adjacent atom.
17. The organometallic compound according to claim 9, wherein R 10 is a group represented by any one selected from Formula 2B-1 to Formula 2B-48 and Formula 2C-1 to Formula 2C-48: In Formulae 2B-1 to 2B-48 and 2C-1 to 2C-48, Z2 to Z4 are the same as those defined in Formula 2, Z 50 is hydrogen, deuterium, or C1-C2-C3-C4-C6-C1-C2 ... 10 alkyl, b50 is an integer from 1 to 5, Z 51 is hydrogen, deuterium, unsubstituted or deuterium-substituted C1-C 10 Alkyl or unsubstituted or deuterated C6-C 20 Aryl, b51 is an integer from 1 to 4, and * indicates the binding site with the adjacent atom.
18. The organometallic compound according to claim 9, wherein At least one selected from Z2 to Z4 in Formula 2 is -CH3, -CD3, -CD2H, -CDH2, or a group represented by any one selected from Formula 8-1 to Formula 8-20: In Formulae 8-1 to 8-20, * represents a bonding site with an adjacent atom.
19. The organometallic compound according to claim 9, wherein Z5 is deuterium, unsubstituted or substituted with at least one R 10a C1-C 20 Alkyl is either unsubstituted or substituted with at least one R 10a C6-C 30 Aryl.
20. The organometallic compound according to claim 9, wherein The organometallic compound is represented by Formula 1-1 or Formula 1-2: Formula 1-1 Formula 1-2 In Formula 1-1 or Formula 1-2, Ring CY2, M1, X2, L1 to L3, n1 to n3, R2, a2 and R 10 are the same as those defined in Formula 1, R 11 to R 13 are independently the same as defined in reference to R1 in Formula 1, a13 is an integer from 1 to 4, R 31 and R 51 are independently the same as defined in reference to R3 in Formula 1, a31 is 1 or 2, and a51 is an integer from 1 to 4, and R 41 to R 44 are independently the same as defined with reference to R4 in Formula 1.
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KR1020240038305A