Organometallic compound, light-emitting device including organometallic compound, and electronic device including light-emitting device

Abstract

The present application relates to an organometallic compound, a light-emitting device including the organometallic compound, and an electronic device including the light-emitting device. The light-emitting device includes a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the light-emitting device contains at least one organometallic compound represented by Formula 1.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0119381, filed with the Korean Intellectual Property Office on September 16, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of this disclosure relate to organometallic compounds, light-emitting devices comprising said organometallic compounds, and electronic devices comprising said light-emitting devices. Background Technology

[0004] Organic light-emitting devices are self-emitting devices that, compared with other devices in the field, have a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage and response speed, and produce full-color images.

[0005] An organic light-emitting device may include a first electrode on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied by the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied by the second electrode can move towards the emitter layer through the electron transport region. Charge carriers such as holes and electrons recombine in the emitter layer to generate excitons. These excitons transition from an excited state to the ground state, thereby generating light. Summary of the Invention

[0006] Organometallic compounds, light-emitting devices comprising said organometallic compounds, and electronic devices comprising said light-emitting devices are provided.

[0007] Additional aspects of the embodiments of this disclosure will be set forth in part in the description which follows and will be apparent in part from the description, or may be learned by practice of the embodiments presented in this disclosure.

[0008] According to an aspect of the implementation scheme, an organometallic compound represented by Formula 1 is provided:

[0009] Formula 1

[0010]

[0011] In Equation 1,

[0012] M1is selected from the group consisting of platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm), Y1and Y2are each independently selected from the group consisting of a carbon atom (C) and a nitrogen atom (N),

[0013] T1to T4are each independently a bond, O, S, B(R'), N(R'), P(R'), C(R')(R”), Si(R')(R”), Ge(R')(R”), C(=O), B(R')(R”), N(R')(R”) or P(R')(R”), wherein, when T1is a bond, Y1and M1are directly bonded to each other, when T2is a bond, Y2and M1are directly bonded to each other, when T3is a bond, the C in ring A1is directly bonded to M1, and when T4is a bond, the C in ring A2is directly bonded to M1,

[0014] two of the bonds between Y1or T1and M1, between Y2or T2and M1, between the C in ring A1or T3and M1, and between the C in ring A2or T4and M1are each a coordination bond, and the remaining two bonds are each a covalent bond,

[0015] X1is C(R1) or N, X2is C(R2) or N, X3is C(R3) or N, X4is C(R4) or N, and X 11 is C(R5)(R6) or N(R5),

[0016] ring A 11 and ring A 12 are each independently selected from the group consisting of C5-C 60 carbocyclic groups and C1-C 60 heterocyclic groups,

[0017] L1to L3are each independently selected from the group consisting of a single bond, a double bond, *-N(R9)-*’, *-B(R9)-*’, *-P(R9)-*’, *-C(R9)(R 10 )-*’, *-Si(R9)(R 10 )-*’, *-Ge(R9)(R 10 )-*’, *-S-*’, *-Se-*’, *-O-*’, *-C(=O)-*’, *-S(=O)-*’, *-S(=O)2-*’, *-C(R9)=*’, *=C(R9)-*’, *-C(R9)=C(R 10 )-*’, *-C(=S)-*’, and *-C≡C-*’,

[0018] a1 to a3 are each an independent integer from 0 to 3. When a1 is 0, A1 and A... 11 They are not connected to each other. When a2 is 0, A 11 and A 12 They are not connected to each other, and when a3 is 0, A2 and A... 12 They are not connected to each other.

[0019] R', R” and R1 to R 12 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or substituted with at least one R 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Arylthioyl groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0020] b11 and b12 are each an independent integer from 0 to 20.

[0021] R1 to R 12 Two adjacent groups in the [substrate] are optionally bonded to form an unsubstituted or [substrate] compound with at least one R [substrate]. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0022] * and *' represent the binding sites with adjacent atoms, and

[0023] R10a is

[0024] deuterium (-D), -F, -CI, -Br, -I, a hydroxyl group, a cyano group, or a nitro group,

[0025] each unsubstituted or substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 carbocyclic group, a C1-C 60 heterocyclic group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or any combination thereof, 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, or a C1-C 60 alkoxy group,

[0026] each unsubstituted or substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 60 carbocyclic group, a C1-C 60 heterocyclic group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or any combination thereof,60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy group or C6-C 60 arylthio group, or

[0027] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),

[0028] wherein Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; a C1-C 60 alkyl group; a C2-C 60 alkenyl group; a C2-C 60 alkynyl group; a C1-C 60 alkoxy group; or a C3-C 60 carbocyclic group or C1-C 60 heterocyclic group, each unsubstituted or substituted with deuterium, -F, a cyano group, a C1-C 60 alkyl group, a C1-C 60 alkoxy group, a phenyl group, a biphenyl group or any combination thereof.

[0029] According to another aspect of the embodiments, there is provided a light-emitting device including: a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the light-emitting device comprises at least one organic metal compound represented by Formula 1.

[0030] According to another aspect of the embodiments, there is provided an electronic device including the light-emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0031] The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description, taken in conjunction with the accompanying drawings, in which:

[0032] Figure 1 schematically illustrates a cross-sectional view of a light emitting device according to embodiments of the present disclosure; and

[0033] Figure 2 and Figure 3 each is a cross-sectional view schematically illustrating a light emitting device according to embodiments of the present disclosure. DETAILED DESCRIPTION

[0034] Reference will now be made in detail to implementations, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present implementations can have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the following detailed description is merely provided to explain aspects of the presently described implementations. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression "at least one of a, b, and c" means only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0035] The organometallic compound is represented by Formula 1:

[0036] Formula 1

[0037]

[0038] M1in Formula 1 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0039] In embodiments, M1may be selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os.

[0040] In embodiments, M1may be Pt or Pd, but embodiments of the present disclosure are not limited thereto.

[0041] In Formula 1, Y1and Y2are each independently selected from a carbon atom (C) and a nitrogen atom (N),

[0042] T1to T4are each independently a bond, O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R"), or P(R')(R"), wherein when T1is a bond, Y1and M1are directly bonded to each other, when T2is a bond, Y2and M1are directly bonded to each other, when T3is a bond, the C in ring A1is directly bonded to M1, and when T4is a bond, the C in ring A2is directly bonded to M1, and

[0043] two of the bonds between Y1or T1and M1, between Y2or T2and M1, between the C in ring A1or T3and M1, and between the C in ring A2or T4and M1are each a coordinate bond, and the remaining two bonds are each a covalent bond. As used herein, the term "bond" can refer to a covalent bond (e.g., a single bond or a single covalent bond), a coordinate bond (e.g., a coordinate covalent bond or a dative bond), or an ionic bond.

[0044] In embodiments, T1to T4may each be a bond.

[0045] In embodiments, Y1and Y2may each be C, although embodiments of the present disclosure are not limited thereto.

[0046] In Formula 1, X1is C(R1) or N, X2is C(R2) or N, X3is C(R3) or N, X4is C(R4) or N, and X 11 is C(R5)(R6) or N(R5).

[0047] In embodiments, X1may be C(R1) or N, X2may be C(R2), X3may be C(R3), and X4may be C(R4).

[0048] In embodiments, X 11 may be C(R5)(R6).

[0049] In embodiments, ring A1may be a group represented by one of Formula 2-1 and Formula 2-2, and ring A2may be a group represented by one of Formula 2-3 and Formula 2-4:

[0050]

[0051] In Formula 2-1 to Formula 2-4,

[0052] X1to X4, X 11 , R7, and R8are the same as described above,

[0053] ring A 13 , and ring A14 each independently selected from C5-C 60 carbocyclic groups and C1-C 60 heterocyclic groups,

[0054] R 13 , R 14 , b13 and b14 are the same as described above for R', R", R1to R 12 , b11 and b12, and

[0055] * denotes the binding site to the adjacent T3or T4, and *' denotes the binding site to the adjacent L1or L3.

[0056] In embodiments, ring A1may be a group represented by one of Formula 2A-1 to Formula 2A-4, and ring A2may be a group represented by one of Formula 2B-1 to Formula 2B-4:

[0057]

[0058] In Formula 2A-1 to Formula 2A-4 and Formula 2B-1 to Formula 2B-4,

[0059] X1to X4, X 11 , R7and R8are the same as described above,

[0060] X 21 is C(R 21 ) or N, X 22 is C(R 22 ) or N, X 23 is C(R 23 ) or N, and X 24 is C(R 24 ) or N,

[0061] Y 21 is C(R 25 )(R 26 ), N(R 25 ), O or S,

[0062] X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, X 34 is C(R 34 ) or N, X 35 is C(R 35 ) or N, and X 36 is C(R 36 ) or N,

[0063] R 21 to R 26 and R 31 to R 36 are the same as described in this specification for R', R" and R1to R 12 and

[0064] * indicates a binding site to an adjacent T3or T4, and *' indicates a binding site to an adjacent L1or L3.

[0065] In Formula 1, ring A 11 and ring A 12 are each independently selected from the group consisting of C5-C 60 carbocyclic groups and C1-C 60 heterocyclic groups.

[0066] In embodiments, ring A 11 and ring A 12 may each independently be selected from the group consisting of:

[0067] phenyl groups, naphthyl groups, anthryl groups, phenanthryl groups, triphenylphenyl groups, pyrenyl groups, a benzothienopyrrolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuranopyrimidine group, a benzothienopyrimidine group, a benzothienopyrrolopyrimidine group, a dihydropyridine 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 2,3-dihydroimidazole group, a triazole group, a 1,2,4-triazole group, a tetrazole group, a 2,3-dihydrotriazole group, an azathienopyrrolo group, a diazathienopyrrolo group, a triazathienopyrrolo 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 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a pyridopyrrolopyridine group, a dihydropyranylolindole group, a dibenzooxaborinocyclohexadiene group, a dihydridodibenzonitaborinocyclohexadiene group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

[0068] In embodiments, ring A 11 and ring A 12 may each independently be selected from:

[0069] a phenyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group, a pyridyl group, an indolopyrimidine group, a pyridopyrrolopyridine group, a dihydropyranylolindole group, a dibenzooxaborinocyclohexadiene group, and a dihydridodibenzonitaborinocyclohexadiene group.

[0070] In Formula 1, L1to L3are each independently selected from a single bond (e.g., a single covalent bond), a double bond (e.g., a double covalent bond), *-N(R9)-*, 10 *-Si(R9)(R 10 *-Ge(R9)(R 10)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R9)=*', *=C(R9)-*', *-C(R9)=C(R 10 )-*', *-C(=S)-*', and *-C≡C-*', where a1 to a3 are each independently selected from integers from 0 to 3. When a1 is 0, A1 and A 11 They are not connected to each other. When a2 is 0, A 11 and A 12 They are not connected to each other. When a3 is 0, A2 and A... 12 They are not connected to each other, and * and *' each represent a binding site with an adjacent atom.

[0071] In the implementation scheme, a1 to a3 can each be 1, L1 and L3 can each be a single bond, and L2 can be *-N(R9)-*', *-B(R9)-*', or *-C(R9)(R 10 )-*'、*-Si(R9)(R 10 )-*', *-S-*' or *-O-*'.

[0072] In Equation 1, R', R” and R1 to R 12 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60Arylthioyl groups, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) and -P(=S)(Q1)(Q2),

[0073] b11 and b12 can each be an integer from 0 to 20 independently, and

[0074] R1 to R 12 Two adjacent groups in the matrix can optionally be bonded to form an unsubstituted or substituted matrix, which is formed by at least one R group. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups.

[0075] In the implementation plan, R', R" and R1 to R 12 Each group can be independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 alkyl groups and C1-C 20 alkoxy group;

[0076] Each is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 alkyl groups and C1-C 20 At least one substituted C1-C alkoxy group 20 alkyl groups and C1-C 20 alkoxy group;

[0077] Cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, norbornyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyrroleyl group, indoleyl group, isoindoleyl group, indazole group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinoxalinyl group, quinoxalinyl group, cyclohexadienyl group, triazineyl group, pyridopyrrolopyridyl group, dihydropyranoindoleyl group, dibenzoxadienocyclohexadienyl group and dihydrodibenzoxadienocyclohexadienyl group;

[0078] Each is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20Alkoxy group, cyclopentyl group, cyclohexyl group, adamantyl group, norbornel group, norbornel alkenyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indole group, isoindoleyl group, indazole group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphineyl group, triazineyl group, pyridopyrrolopyridyl group, dihydropyranoindoleyl group, dibenzoxadienocyclohexadienyl group, dihydrodibenzoxadienocyclohexadienyl group, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) and -P(=O)(Q 31 (Q) 32 At least one substituted cyclopentyl group, cyclohexyl group, adamantyl group, norbornel group, norbornel alkenyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indole group, isoindoleyl group, indazole group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinoxalinyl group, quinoxalinyl group, cyclooxalinyl group, triazinyl group, pyridopyrrolopyridyl group, dihydropyranoindoleyl group, dibenzoxaziborhexacyclohexadienyl group and dihydrodibenzoxaziborhexacyclohexadienyl group;

[0079] Each is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, adamantyl groups, norbornel groups, norbornel alkenyl groups, phenyl groups, naphthyl groups, pyridyl groups, pyrimidyl groups, pyrazinyl groups, pyridazinyl groups, indole groups, isoindole groups, indazole groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, quinoxalinyl groups, quinazolinyl groups, cyclophosphine groups, triazine groups, pyridopyrrolopyridyl groups, dihydropyranoindole groups, dibenzoxadienocyclohexadienyl groups and dihydrodibenzoxadienocyclohexadienyl groups, -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), each of which can be optionally substituted with at least one of the following: a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolinyl group, a cinnolinyl group, a triazinyl group, a pyrrolopyrrolopyridinyl group, a dihydropyranoindolyl group, a dibenzoxaborinyl group, and a dihydrodibenzazaborinyl group; and

[0080] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2),

[0081] wherein Q1to Q3and Q 31 to Q 33 may each be independently selected from:

[0082] hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C1-C 20 alkyl group, a C2-C 20 alkenyl group, a C2-C 20 alkynyl group, a C1-C 20 alkoxy group, a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 20 aryl group, a C1-C 20heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0083] In embodiments, the organometallic compound represented by Formula 1 can be an organometallic compound represented by Formula 1-1:

[0084] Formula 1-1

[0085]

[0086] In Formula 1-1,

[0087] M1, X1to X4, X 11 , Y1, Y2, L1to L3, R7, and R8are the same as described above,

[0088] X 41 is C(R 41 ) or N, X 42 is C(R 42 ) or N, X 43 is C(R 43 ) or N, X 44 is C(R 44 ) or N, X 45 is C(R 45 ) or N, and X 46 is C(R 46 ) or N, and

[0089] R 41 to R 46 are the same as described above in relation to R', R", and R1to R 12 .

[0090] In embodiments, in Formula 1-1, R1to R 12 and R 41 to R 46 may optionally be bonded to each other to form a C5-C 10a carbocyclic group unsubstituted or substituted with at least one R 60 or a C1-C 10a heterocyclic group unsubstituted or substituted with at least one R 60 .

[0091] In embodiments, the organometallic compound represented by Formula 1 can be selected from the group consisting of Compound 1 to Compound 120, but embodiments of the present disclosure are not limited thereto:

[0092]

[0093]

[0094]

[0095]

[0096] Because one of the ligands bonded to the central metal (M1 in Formula 1) in the organometallic compound represented by Formula 1 includes a 6-membered ring carbene ligand, the binding force between the central metal and the carbene ligand is enhanced, and thus the rigidity of the organometallic compound can be improved. Accordingly, the lifespan characteristics of the organic light-emitting device using the organometallic compound can be improved.

[0097] Optionally, because the 6-membered ring carbene ligand in the organometallic compound represented by Formula 1 has a fused ring structure, the metal-to-ligand charge transfer transition (MLCT) is increased due to an increase in the sigma binding force (e.g., due to an increase in the sigma electron orbital participation in bonding), and thus the stability of the organic light-emitting device using the organometallic compound can be increased.

[0098] Further, because the organometallic compound represented by Formula 1 includes both a 5-membered ring carbene ligand and a 6-membered ring carbene ligand, the ligand-to-ligand charge transfer transition (LLCT) can be additionally suppressed or reduced, thereby improving the color purity.

[0099] Accordingly, when the organometallic compound is applied to an organic light-emitting device, the triplet exciton can be prevented from being transferred to a non-emitting 3 the phenomenon of the MC state (metal center triplet state) (or the occurrence or likelihood of such transfer can be reduced), such that the stability of the excited state is excellent, and the organic light-emitting device can have excellent lifespan and efficiency characteristics.

[0100] The organometallic compound can emit blue light. In an embodiment, the organometallic compound can emit blue light having a maximum emission wavelength of about 410 nm or more and about 500 nm or less (bottom emission CIE x,y color coordinates x = 0.13 and y = 0.05 to 0.20), but embodiments of the present disclosure are not limited thereto. Accordingly, the organometallic compound represented by Formula 1 can be used to manufacture a light-emitting device that emits blue light.

[0101] A person of ordinary skill in the art can recognize the synthesis method of the organometallic compound represented by Formula 1 by referring to the examples provided below.

[0102] At least one of the organometallic compounds represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Accordingly, a light-emitting device is provided, which includes a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the light-emitting device contains an organometallic compound represented by Formula 1.

[0103] In an embodiment,

[0104] The intermediate layer can further include a hole transport zone between the first electrode and the emission layer and an electron transport zone between the emission layer and the second electrode,

[0105] The hole transport zone can include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and

[0106] The electron transport zone can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0107] In one or more embodiments, the organometallic compound can be contained between a pair of electrodes of a light-emitting device. Accordingly, the organometallic compound can be contained in an intermediate layer of a light-emitting device, for example, in an emission layer of the intermediate layer. The organometallic compound contained in the emission layer can act as a dopant. In one or more embodiments, the organometallic compound represented by Formula 1 can be used as a material for a capping layer located outside a pair of electrodes of a light-emitting device.

[0108] In one or more embodiments, the second capping layer is on the second electrode, and

[0109] The second capping layer can contain a material having a refractive index of 1.6 or greater than 1.6 at a wavelength of 589 nm.

[0110] In an embodiment, the emission layer can contain the organometallic compound.

[0111] In an embodiment, the emission layer can further contain a host, and the amount of the organometallic compound can be 0.01 parts by weight to 49.99 parts by weight, based on 100 parts by weight of the emission layer.

[0112] In an embodiment, the host can include a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof.

[0113] In an embodiment, the emission layer can emit blue light having a maximum emission wavelength of 410 nm to 500 nm.

[0114] In an embodiment, the electron transport zone can contain a phosphine oxide-containing compound, a silyl compound, or any combination thereof.

[0115] In one or more embodiments, the light-emitting device can further include at least one selected from a first cover layer positioned outside the first electrode and a second cover layer positioned outside the second electrode, and at least one selected from the first cover layer and the second cover layer can contain the organometallic compound represented by Formula 1. Other details of the first cover layer and / or the second cover layer are the same as described elsewhere in this specification.

[0116] In embodiments, the light-emitting device can include:

[0117] a first cover layer positioned outside the first electrode and containing the organometallic compound represented by Formula 1;

[0118] a second cover layer positioned outside the second electrode and containing the organometallic compound represented by Formula 1; or

[0119] the first cover layer and the second cover layer.

[0120] The phrase “the (interlayer and / or cover layer) contains an organometallic compound” as used herein can be understood as “the (interlayer and / or cover layer) can contain one kind of organometallic compound represented by Formula 1 or two different kinds of organometallic compounds each represented by Formula 1”.

[0121] For example, the interlayer and / or the cover layer can contain only Compound 1 as the organometallic compound. In this regard, Compound 1 can be present in an emission layer of the light-emitting device. In one or more embodiments, the interlayer can contain Compound 1 and Compound 2 as the organometallic compounds. In this regard, Compound 1 and Compound 2 are present in the same layer (e.g., Compound 1 and Compound 2 can both be present in the emission layer), or are present in different layers (e.g., Compound 1 can be present in the emission layer, and Compound 2 can be present in an electron transport region).

[0122] The term “interlayer” as used herein refers to a single layer or multiple layers between the first electrode and the second electrode in the light-emitting device.

[0123] Figure 1 Description of FIGS.

[0124] Figure 1 is a schematic cross-sectional view of a light-emitting device 10 according to embodiments. The light-emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.

[0125] Hereinafter, structures of the light-emitting device 10 according to embodiments and methods of manufacturing the light-emitting device 10 will be described. Figure 1

[0126] ​The first electrode 110

[0127] In Figure 1 The substrate can be additionally positioned under the first electrode 110 or over the second electrode 150. The substrate can be a glass substrate and / or a plastic substrate. The substrate can be a flexible substrate. In one or more embodiments, the substrate can include a plastic having excellent heat resistance and / or durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0128] The first electrode 110 can be formed by, for example, depositing and / or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a high work function material into which holes can be easily injected can be used as the material for forming the first electrode 110.

[0129] The first electrode 110 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 can include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used as the material for forming the first electrode 110.

[0130] The first electrode 110 can have a single layer structure including (e.g., consisting of) a single layer or a multi-layer structure including a plurality of layers. In an embodiment, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO.

[0131] The intermediate layer 130

[0132] The intermediate layer 130 is on the first electrode 110. The intermediate layer 130 includes an emission layer.

[0133] The intermediate layer 130 can further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.

[0134] In addition to various suitable organic materials, the intermediate layer 130 can further include a metal-containing compound (e.g., an organometallic compound), an inorganic material (e.g., a quantum dot), etc.

[0135] In one or more embodiments, the intermediate layer 130 may include i) two or more emitting units stacked sequentially between the first electrode 110 and the second electrode 150, and ii) a charge generating layer located between two emitting units. When the intermediate layer 130 includes emitting units and a charge generating layer, the light-emitting device 10 may be a series light-emitting device.

[0136] Hole transport region in intermediate layer 130

[0137] The hole transport region may have: i) a single-layer structure comprising (e.g., composed of): a single layer containing a single material (e.g., composed of a single material), ii) a single-layer structure comprising (e.g., composed of): a single layer containing multiple different materials, or iii) a multi-layer structure comprising multiple layers containing different materials.

[0138] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.

[0139] For example, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein, in each structure, the layers are stacked sequentially from the first electrode 110.

[0140] The hole transport region may contain a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0141] Formula 201

[0142]

[0143] Formula 202

[0144]

[0145] In equations 201 and 202,

[0146] L 201 To L 204 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0147] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201)-*', unsubstituted or by at least one R 10a Replacement C1-C 20 alkylene groups, unsubstituted or with at least one R 10a Replacement C2-C 20 alkenyl groups, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0148] xa1 to xa4 can each be an integer from 0 to 5 independently.

[0149] xa5 can be an integer from 1 to 10, and

[0150] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0151] R 201 and R 202 It can be optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., see compound HT16 below),

[0152] R 203 and R 204 It can be optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and

[0153] na1 can be an integer from 1 to 4.

[0154] In embodiments, Formula 201 and Formula 202 can each include at least one of the groups represented by Formula CY201 through Formula CY217:

[0155]

[0156] With respect to Formula CY201 through Formula CY217, R 10b and R 10c are the same as described with respect to R 10a Ring CY 201 through Ring CY 204 may each independently be a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group, and at least one hydrogen in Formula CY201 through Formula CY217 can be unsubstituted or substituted with at least one R 10a described herein.

[0157] In embodiments, Ring CY 201 through Ring CY 204 in Formula CY201 through Formula CY217 can each independently be a phenyl group, a naphthyl group, a phenanthryl group, or an anthryl group.

[0158] In embodiments, Formula 201 and Formula 202 can each include at least one of the groups represented by Formula CY201 through Formula CY203.

[0159] In one or more embodiments, Formula 201 can include at least one of the groups represented by Formula CY201 through Formula CY203 and at least one of the groups represented by Formula CY204 through Formula CY217.

[0160] In one or more embodiments, in Formula 201, xa1 is 1, R 201 is a group represented by one selected from Formula CY201 through Formula CY203, xa2 is 0, R 202 is a group represented by one selected from Formula CY204 through Formula CY207.

[0161] In one or more embodiments, each of Formula 201 and Formula 202 can not include a group represented by one selected from Formula CY201 through Formula CY203.

[0162] In one or more embodiments, each of Formula 201 and Formula 202 can not include a group represented by one selected from Formula CY201 through Formula CY203 and can include at least one of the groups represented by Formula CY204 through Formula CY217.

[0163] In embodiments, each of Formula 201 and Formula 202 can not include a group represented by one selected from Formula CY201 to Formula CY217.

[0164] In embodiments, the hole transport zone can include one selected from Compound HT1 to Compound HT44, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, Methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl) triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The thickness of the hole transport zone can be about to about For example, about to about When the hole transport zone includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer can be about to about For example, about to about and the thickness of the hole transport layer can be about to about For example, about to about When the thickness of the hole transport zone, the hole injection layer, and the hole transport layer is within these ranges, suitable or satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0171] The emission auxiliary layer can increase light emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport zone. The emission auxiliary layer and the electron blocking layer can include materials as described above.

[0172] p-dopant

[0173] In addition to these materials, the hole transport zone can further include a charge generating material for improving the conduction property (e.g., the electrical property). The charge generating material can be uniformly or non-uniformly dispersed in the hole transport zone (e.g., in the form of a single layer of the charge generating material).

[0174] The charge generating material can be, for example, a p-dopant.

[0175] In embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be -3.5 eV or less than -3.5 eV.

[0176] In embodiments, the p-dopant can include a quinone derivative, a cyano group-containing compound, a compound containing an element EL1 and an element EL2, or any combination thereof.

[0177] Examples of the quinone derivative can include TCNQ and F4-TCNQ.

[0178] Examples of the cyano group-containing compound can include HAT-CN and a compound represented by the following Formula 221.

[0179]

[0180] Formula 221

[0181]

[0182] In Formula 221,

[0183] R 221 to R 223 may each independently be an unsubstituted or substituted C1-C 10a alkyl group, or any combination thereof. 60 carbon ring group, or an unsubstituted or substituted C1-C 10a heterocyclic group, and

[0184] R 221 to R 223 At least one of R 20 may each independently be each substituted with: a cyano group; -F; -Cl; -Br; -I; a C1-C 60 alkyl group substituted with a cyano group, -F, -Cl, -Br, -I, or any combination thereof; or a C3-C 60 carbon ring group or a C1-C 301 heterocyclic group.

[0185] With respect to the compound containing element EL1 and element EL2, element EL1 can be a metal, a metalloid, or a combination thereof, and element EL2 can be a nonmetal, a metalloid, or a combination thereof.

[0186] Examples of metals can include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), 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), gold (Au), etc.); post-transition metals (e.g., zinc (Zn), indium (In), 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), lutetium (Lu), etc.).

[0187] Examples of metalloids can include silicon (Si), antimony (Sb), and tellurium (Te).

[0188] Examples of nonmetals can include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).

[0189] In embodiments, examples of the compound containing element EL1 and element EL2 can include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, and / or a metal iodide), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, or a metalloid iodide), a metal telluride, or any combination thereof.

[0190] Examples of metal oxides can include tungsten oxides (e.g., WO, W2O3, WO2, WO3, and / or W2O5), vanadium oxides (e.g., VO, V2O3, VO2, and / or V2O5), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, and / or Mo2O5), and rhenium oxides (e.g., ReO3).

[0191] Examples of metal halides can include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0192] Examples of alkali metal halides can include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

[0193] Examples of alkaline earth metal halides can include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.

[0194] Examples of transition metal halides can include titanium halides (e.g., TiF4, TiCl4, TiBr4, and / or TiI4), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, and / or ZrI4), hafnium halides (e.g., HfF4, HfCl4, HfBr4, and / or HfI4), vanadium halides (e.g., VF3, VCl3, VBr3, and / or VI3), niobium halides (e.g., NbF3, NbCl3, NbBr3, and / or NbI3), tantalum halides (e.g., TaF3, TaCl3, TaBr3, and / or TaI3), chromium halides (e.g., CrF3, CrCl3, CrBr3, and / or CrI3), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, and / or MoI3), tungsten halides (e.g., WF3, WCl3, WBr3, and / or WI3), manganese halides (e.g., MnF2, MnCl2, MnBr2, and / or MnI2), technetium halides (e.g., TcF2, TcCl2, TcBr2, and / or TcI2), rhenium halides (e.g., ReF2, ReCl2, ReBr2, and / or ReI2), iron halides (e.g., FeF2, FeCl2, FeBr2, and / or FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, and / or RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2, and / or OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2, and / or CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2, and / or RhI2), iridium halides (e.g., IrF2, IrCl2, IrBr2, and / or IrI2), nickel halides (e.g., NiF2, NiCl2, NiBr2, and / or NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2, and / or PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2, and / or PtI2), copper halides (e.g., CuF, CuCl, CuBr, and / or CuI), silver halides (e.g., AgF, AgCl, AgBr, and / or AgI), and gold halides (e.g., AuF, AuCl, AuBr, and / or AuI).

[0195] Examples of post-transition metal halides can include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, and / or ZnI2), indium halides (e.g., InI3), and tin halides (e.g., SnI2).

[0196] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.

[0197] Examples of metal halide quasi-metal halides can include antimony halides (e.g., SbCl5).

[0198] Examples of metal tellurides can include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te and / or Cs₂Te), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, etc.). FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te), post-transition metal tellurides (e.g., ZnTe) and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe).

[0199] The emission layer in intermediate layer 130

[0200] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer, depending on the sub-pixel. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from the red, green, and blue emitting layers, wherein the two or more layers are in contact with each other (e.g., physical contact) or separated from each other to emit white light. In one or more embodiments, the emitting layer may contain two or more materials selected from the red-emitting, green-emitting, and blue-emitting materials, wherein the two or more materials are mixed together in a single layer to emit white light.

[0201] The emitting layer may comprise a host and dopants. Dopants may include phosphorescent dopants, fluorescent dopants, or any combination thereof.

[0202] Based on 100 parts by weight of the host, the amount of dopant in the emitter layer can be from about 0.01 parts by weight to about 15 parts by weight.

[0203] In one or more embodiments, the emitter layer may contain quantum dots.

[0204] In some implementations, the emission layer may contain a delayed fluorescence material. The delayed fluorescence material may act as a host or dopant in the emission layer.

[0205] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitting layer is within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0206] main body

[0207] The main body may include silicon-containing compounds, phosphine oxide-containing compounds, or any combination thereof, as described above.

[0208] In the implementation scheme, the main component may include a compound represented by the following formula 301:

[0209] Formula 301

[0210] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0211] In Equation 301,

[0212] Ar 301 and L 301 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0213] xb11 can be 1, 2, or 3.

[0214] xb1 can be an integer from 0 to 5.

[0215] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C60 alkynyl group, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkoxy group, unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 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 ),

[0216] xb21may be an integer from 1 to 5, and

[0217] Q 301 to Q 303 are the same as described for Q1.

[0218] In one or more embodiments, when xb11in Formula 301 is 2 or greater than 2, two or more Ar 301 may be connected to each other via a single bond.

[0219] In embodiments, the host can include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0220] Formula 301-1

[0221]

[0222] Formula 301-2

[0223]

[0224] In Formula 301-1 and Formula 301-2,

[0225] Ring A 301 to Ring A 304 may each independently be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group,

[0226] X 301 may be O, S, N[(L 304 ) xb4 -R 304 ], C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0227] xb22and xb23may each independently be 0, 1 or 2,

[0228] L 301 , xb1and R 301 are the same as described in the specification,

[0229] L 302 through L 304 may each independently be the same as described with respect to L 301 ,

[0230] xb2through xb4may each independently be the same as described with respect to xb1, and

[0231] R 302 through R 305 and R 311 through R 314 are the same as described with respect to R 301 .

[0232] In one or more embodiments, the host can include an alkaline earth metal complex. In embodiments, the host can be a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0233] In one or more embodiments, the host can include one or any combination of compound H1 through compound H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP):

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240] Phosphorescent dopant

[0241] The dopant can include an organometallic compound represented by Formula 1.

[0242] In an embodiment, the phosphorescent dopant can include at least one transition metal as a central metal.

[0243] The phosphorescent dopant can include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0244] The phosphorescent dopant can be electrically neutral.

[0245] In one or more embodiments, the phosphorescent dopant can include an organometallic compound represented by Formula 401:

[0246] Formula 401

[0247] M(L 401 ) xc1 (L 402 ) xc2

[0248] Formula 402

[0249]

[0250] In Formula 401 and Formula 402,

[0251] M can be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0252] L 401 may be a ligand represented by Formula 402, and xc1may be 1, 2, or 3, wherein when xc1is 2 or more than 2, two or more than two L 401 may be the same as or different from each other,

[0253] L 402 may be an organic ligand, and xc2may be 0, 1, 2, 3, or 4, wherein when xc2is 2 or more than 2, two or more than two L 402 may be the same as or different from each other,

[0254] X401 and X 402 It can be either nitrogen or carbon, each independently.

[0255] Ring A 401 And Ring A 402 Each can be C3-C independently. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0256] 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 = *',

[0257] X 403 and X 404 These can be chemical bonds (e.g., monocovalent or coordinate bonds, e.g., coordinate-covalent or coordinate-valent bonds)), O, S, N (Q) independently. 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),

[0258] Q 411 To Q 414 Same as described regarding Q1,

[0259] R 401 and R 402 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 alkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 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 ),

[0260] Q 401 To Q 403 Same as described regarding Q1,

[0261] xc11 and xc12 can each be an integer from 0 to 10 independently, and

[0262] In Equation 402, * and *' each represent the binding site with M in Equation 401.

[0263] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each of them can be nitrogen.

[0264] In one or more embodiments, when xc1 in equation 401 is 2 or greater than 2, two or more L 401 The two rings A in 401 It can be optionally via T as a linking group 402 Connected to each other, or two or more L's 401 The two rings A in 402 It can be optionally via T as a linking group 403 They are interconnected (see compounds PD1 through PD4 and PD7). T 402 and T 403 Regarding T 401 The descriptions are the same.

[0265] L in Equation 401 402 It can be an organic ligand. In one or more embodiments, L 402 It can be a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a pyridine carboxylate group), a -C (=O), an isonitrile group, a -CN group, a phosphorus group (e.g., a phosphine group or a phosphite group), or any combination thereof.

[0266] Phosphorescent dopants may include, for example, one or any combination of the following compounds PD1 to PD25:

[0267]

[0268]

[0269] Fluorescent dopants

[0270] Fluorescent dopants may include compounds containing amine groups, compounds containing styrene groups, or any combination thereof.

[0271] In one or more embodiments, the fluorescent dopant may include a compound represented by formula 501:

[0272] Formula 501

[0273]

[0274] In Equation 501,

[0275] Ar 501 L 501 To L 503 R 501 and R 502 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0276] xd1 to xd3 can each be independently 0, 1, 2, or 3, and

[0277] xd4 can be 1, 2, 3, 4, 5, or 6.

[0278] In one or more embodiments, Ar in Formula 501 501 It can be a fused cyclic group (e.g., anthracene group, etc.) in which three or more monocyclic groups are fused together (e.g., combined together). (group or pyrene group).

[0279] In one or more embodiments, xd4 in Formula 501 can be 2.

[0280] In the implementation scheme, the fluorescent dopant may include one or any combination of the following compounds FD1 to FD36, DPVBi, DPAVBi:

[0281]

[0282]

[0283]

[0284] delayed fluorescence material

[0285] The emission layer can include a delayed fluorescence material.

[0286] The delayed fluorescence material used herein can be selected from any suitable compound capable of emitting light of delayed fluorescence based on a delayed fluorescence emission mechanism.

[0287] The delayed fluorescence material included in the emission layer can act as a host or a dopant depending on the type (or composition) of other materials included in the emission layer.

[0288] In an embodiment, the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material can be 0 eV or more and 0.5 eV or less. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, the up-conversion of the delayed fluorescence material from the triplet state to the singlet state can be effectively induced, and thus the light-emitting efficiency of the light-emitting device 10 can be improved.

[0289] In an embodiment, the delayed fluorescence material can include i) a material including at least one electron donor (e.g., a π-electron rich C3-C 60 cyclic group, such as a carbazole group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, or a C1-C 60 cyclic group containing a π-electron deficient nitrogen), ii) a material including a C8-C 60 polycyclic group in which two or more cyclic groups share boron (B) and are fused (e.g., combined together) with each other.

[0290] The delayed fluorescence material can include at least one selected from the group consisting of Compound DF1 to Compound DF9:

[0291]

[0292] quantum dot

[0293] The emission layer can include a quantum dot.

[0294] The term “quantum dot” as used herein refers to a crystal of a semiconductor compound, and can include any suitable material capable of emitting light of various suitable emission wavelengths depending on the size of the crystal.

[0295] The diameter of the quantum dot can be, for example, about 1 nm to about 10 nm.

[0296] The quantum dot can be synthesized by a wet-chemical process, a metal-organic chemical vapor deposition process, a molecular beam epitaxy process, and / or a process similar to these processes.

[0297] A wet-chemical process refers to a method in which a solvent and a precursor material are mixed and then quantum dot particles are grown. When the crystal is grown, the organic solvent acts as a dispersant that is naturally coordinated to the surface of the quantum dot crystal and controls the growth of the crystal. Accordingly, by using a process that is easy to perform at a low cost compared to a gas phase deposition process (e.g., a metal organic chemical vapor deposition (MOCVD) process and a molecular beam epitaxy (MBE) process), the growth of quantum dot particles can be controlled.

[0298] The quantum dot can include a II-VI semiconductor compound, a III-V semiconductor compound, a III-VI semiconductor compound, a I-III-VI semiconductor compound, a IV-VI semiconductor compound, a IV element or compound; or any combination thereof.

[0299] Examples of the II-VI semiconductor compound can include a binary compound such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and / or MgS; a ternary compound such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and / or MgZnS; a quaternary compound such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and / or HgZnSTe; or any combination thereof.

[0300] Examples of Group III-V semiconductor compounds can include binary compounds, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb; ternary compounds, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; or any combination thereof. The Group III-V semiconductor compounds can further include Group II elements. Examples of Group III-V semiconductor compounds further including Group II elements can include InZnP, InGaZnP, and / or InAlZnP.

[0301] Examples of Group III-VI semiconductor compounds can include binary compounds, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, and / or InTe; ternary compounds, such as InGaS3and / or InGaSe3; or any combination thereof.

[0302] Examples of Group I-III-VI semiconductor compounds can include ternary compounds, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, and / or AgAlO2, or any combination thereof.

[0303] Examples of Group IV-VI semiconductor compounds can 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; or any combination thereof.

[0304] In embodiments, the Group IV element or compound can include a single element, such as Si or Ge; a binary compound, such as SiC and / or SiGe; or any combination thereof.

[0305] Each element included in the multi-element compound (e.g., binary compound, ternary compound, and quaternary compound) can be present in the particle at a uniform concentration or a non-uniform concentration.

[0306] In some embodiments, the quantum dots can have a single structure or a double structure of core-shell having a uniform (e.g., substantially uniform) concentration of each element included in the respective quantum dot. In embodiments, the material included in the core can be different from the material included in the shell.

[0307] The shell of the quantum dot can function as a protective layer for maintaining the semiconductor property by preventing or reducing chemical degradation of the core, and / or can function as a charging layer for imparting electrophoretic property 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 in a direction toward the center.

[0308] Examples of the shell of the quantum dot can be an oxide of a metal, a metalloid, or a non-metal, a semiconductor compound, or any combination thereof. Examples of the oxide of the metal, the metalloid, or the non-metal can include a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO; a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4; or any combination thereof. Examples of the semiconductor compound as described herein can include a Group II-VI semiconductor compound, a Group III-V semiconductor compound, a Group III-VI semiconductor compound, a Group I-III-VI semiconductor compound, a Group IV-VI semiconductor compound, or any combination thereof. In embodiments, the semiconductor compound can 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.

[0309] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot can be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less. When the FWHM of the emission wavelength spectrum of the quantum dot is in this range, color purity or color reproducibility can be improved. In addition, light emitted by such quantum dots is omnidirectional (e.g., substantially in every direction). Thus, a wide viewing angle can be increased.

[0310] Further, the quantum dots can be, for example, spherical, pyramidal, multi-armed, and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, and / or nanoplates.

[0311] By adjusting the size of the quantum dots, the band gap can also be adjusted, thereby obtaining light of various suitable wavelengths in the quantum dot emissive layer. Thus, by using quantum dots of different sizes, light emitting devices that emit light of various suitable wavelengths can be realized. In more detail, the size of the quantum dots can be selected to emit red light, green light, and / or blue light. Further, the size of the quantum dots can be adjusted such that light of various suitable colors is combined to emit white light.

[0312] Electron transport zone in the intermediate layer 130

[0313] The electron transport zone can have i) a single layer structure including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single layer structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including different materials.

[0314] The electron transport zone can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0315] In embodiments, the electron transport zone can have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein, for each structure, the constituent layers are stacked in order from the emissive layer.

[0316] The electron transport zone can include a phosphine oxide-containing compound, a silyl compound, or any combination thereof, as described above.

[0317] In embodiments, the electron transport zone (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport zone) can include a C1-C 60 Metal-free compound of the cyclic group.

[0318] In embodiments, the electron transport zone can include a compound represented by the following Formula 601:

[0319] Formula 601

[0320] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0321] In Equation 601,

[0322] Ar 601 and L 601 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0323] xe11 can be 1, 2, or 3.

[0324] xe1 can be 0, 1, 2, 3, 4, or 5.

[0325] R 601 It can be unsubstituted or replaced by at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ), Q 601 To Q 603 Same as described regarding Q1,

[0326] xe21 can be 1, 2, 3, 4, or 5, and

[0327] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted C1-C nitrogen containing π-electron-deficient atoms 60 Cyclic groups.

[0328] In one or more embodiments, when xe11 in formula 601 is 2 or greater than 2, two or more Ar 601 They can be connected to each other via a single key.

[0329] In the implementation scheme, Ar in Formula 601 601 It can be a substituted or unsubstituted anthracene group.

[0330] In the implementation scheme, the electron transport region may comprise a compound represented by formula 601-1:

[0331] Formula 601-1

[0332]

[0333] In Equation 601-1,

[0334] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,

[0335] L 611 To L 613 You can refer to L 601 To understand from the presented description,

[0336] xe611 to xe613 can be understood by referring to the description of xe1 presentation.

[0337] R 611 To R 613 You can refer to information about R 601 To understand from the presented description, and

[0338] R 614 To R 616 Each of these can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups.

[0339] In the implementation scheme, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each be 0, 1 or 2 independently.

[0340] The electron transport region may contain one or any combination of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1):

[0341]

[0342]

[0343]

[0344]

[0345] The thickness of the electron transport region can be from about 0.1 nm to about 1000 nm. from about 1 nm to about 100 nm. for example, from about 1 nm to about 50 nm. from about 1 nm to about 100 nm. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be from about 0.1 nm to about 100 nm. from about 1 nm to about 100 nm. for example, from about 1 nm to about 50 nm. from about 1 nm to about 100 nm. and the thickness of the electron transport layer can be from about 0.1 nm to about 1000 nm. from about 1 nm to about 100 nm. for example, from about 1 nm to about 50 nm. from about 1 nm to about 100 nm. 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 these ranges, suitable or satisfactory electron transport properties can be obtained without a significant increase in driving voltage.

[0346] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) can further comprise a metal- containing material.

[0347] 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, and / 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, and / or a Ba ion. The ligand coordinated to the metal ion of the alkali metal complex or the alkaline earth metal complex can include a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.

[0348] In embodiments, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1 (LiQ) or compound ET-D2:

[0349]

[0350] The electron transport region can include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer can directly contact (e.g., physically contact) the second electrode 150.

[0351] The electron injection layer can have: i) a single layer structure that includes (e.g., consists of): a single layer comprising (e.g., consisting of) a single material, ii) a single layer structure that includes (e.g., consists of): a single layer comprising a plurality of different materials, or iii) a multi-layer structure that includes a plurality of layers comprising different materials.

[0352] The electron injection layer can comprise an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0353] 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.

[0354] The alkali metal-containing compound, the alkaline earth metal-containing compound, and / or the rare earth metal-containing compound can be an oxide and / or a halide (e.g., a fluoride, a chloride, a bromide, and / or an iodide) of the alkali metal, the alkaline earth metal, and the rare earth metal, a telluride, or any combination thereof.

[0355] The alkali metal-containing compound can be an alkali metal oxide (e.g., Li2O, Cs2O, and / or K2O), an alkali metal halide (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI), or any combination thereof. The alkaline earth metal-containing compound can include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba x Sr 1-x O (x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-xO (x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound can include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In embodiments, the rare earth metal-containing compound can include lanthanide tellurides. Examples of lanthanide tellurides can include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.

[0356] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex can include i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal, and ii) a ligand bonded to the metal ion, such as a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyl-oxazole, a hydroxyphenyl-thiazole, a hydroxyphenyl-oxadiazole, a hydroxyphenyl-thiadiazole, a hydroxyphenyl-pyridine, a hydroxyphenyl-benzimidazole, a hydroxyphenyl-benzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.

[0357] The electron injection layer can include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, or can further include an organic material (e.g., a compound represented by Formula 601).

[0358] In embodiments, the electron injection layer can include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In embodiments, the electron injection layer can be a KI:Yb co-deposited layer and / or a RbI:Yb co-deposited layer.

[0359] When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof can be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0360] The thickness of the electron injection layer can be about 0.1 nm to about 1000 nm, about 0.1 nm to about 500 nm, about 0.1 nm to about 200 nm, about 0.1 nm to about 100 nm, about 0.1 nm to about 50 nm, about 0.1 nm to about 20 nm, about 0.1 nm to about 10 nm, about 0.1 nm to about 5 nm, about 0.1 nm to about 2 nm, about 0.1 nm to about 1 nm, about 0.1 nm to about 0.5 nm, about 0.1 nm to about 0.2 nm, about 0.1 nm to about 0.1 nm, about 0.1 nm to about 0.05 nm, about 0.1 nm to about 0.02 nm, about 0.1 nm to about 0.01 nm, about 0.1 nm to about 0.005 nm, about 0.1 nm to about 0.002 nm, about 0.1 nm to about 0.001 nm, about 0.1 nm to about 0.0005 nm, about 0.1 nm to about 0.0002 nm, about 0.1 nm to about 0.0001 nm, about 0.1 nm to about 0.00005 nm, about 0.1 nm to about 0.00002 nm, about 0.1 nm to about 0.00001 nm, about 0.1 nm to about 0.000005 nm, about 0.1 nm to about 0.000002 nm, about 0.1 nm to about 0.000001 nm, about 0.1 nm to about 0.0000005 nm, about 0.1 nm to about 0.0000002 nm, about 0.1 nm to about 0.0000001 nm, about 0.1 nm to about 0.00000005 nm, about 0.1 nm to about 0.00000002 nm, about 0.1 nm to about 0.00000001 nm, about 0.1 nm to about 0.000000005 nm, about 0.1 nm to about 0.000000002 nm, about 0.1 nm to about 0.000000001 nm, about 0.1 nm to about 0.0000000005 nm, about 0.1 nm to about 0.0000000002 nm, about 0.1 nm to about 0.0000000001 nm, about 0.1 nm to about 0.00000000005 nm, about 0.1 nm to about 0.00000000002 nm, about 0.1 nm to about 0.00000000001 nm, about 0.1 nm to about 0.000000000005 nm, about 0.1 nm to about 0.000000000002 nm, about 0.1 nm to about 0.000000000001 nm, about 0.1 nm to about 0.0000000000005 nm, about 0.1 nm to about 0.0000000000002 nm, about 0.1 nm to about 0.0000000000001 nm, about 0.1 nm to about 0.00000000000005 nm, about 0.1 nm to about 0.00000000000002 nm, about 0.1 nm to about 0.00000000000001 nm, about 0.1 nm to about 0.000000000000005 nm, about 0.1 nm to about 0.000000000000002 nm, about 0.1 nm to about 0.000000000000001 nm, about 0.1 nm to about 0.0000000000000005 nm, about 0.1 nm to about 0.0000000000000002 nm, about 0.1 nm to about 0.0000000000000001 nm, about 0.1 nm to about 0.00000000000000005 nm, about 0.1 nm to about 0.00000000000000002 nm, about 0.1 nm to about 0.00000000000000001 nm, about 0.1 nm to about 0.000000000000000005 nm, about 0.1 nm to about 0.000000000000000002 nm, about 0.1 nm to about 0.000000000000000001 nm, about 0.1 nm to about 0.0000000000000000005 nm, about 0.1 nm to about 0.0000000000000000002 nm, about 0.1 nm to about 0.0000000000000000001 nm, about 0.1 nm to about 0.00000000000000000005 nm, about 0.1 nm to about 0.00000000000000000002 nm, about 0.1 nm to about 0.00000000000000000001 nm, about 0.1 nm to about 0.000000000000000000005 nm, about 0.1 nm to about 0.000000000000000000002 nm, about 0.1 nm to about 0.000000000000000000001 nm, about 0.1 nm to about 0.0000000000000000000005 nm, about 0.1 nm to about 0.0000000000000000000002 nm, about 0.1 nm to about 0.0000000000000000000001 nm, about 0.1 nm to about 0.000000000000 to about For example, about to about When the thickness of the electron injection layer is in the above-described range, the electron injection layer can have suitable or satisfactory electron injection properties without a significant increase in driving voltage.

[0361] The second electrode 150

[0362] The second electrode 150 can be on the intermediate layer 130 having such a structure. The second electrode 150 can be a cathode as an electron injection electrode, and a metal, an alloy, a conductive compound, or any combination thereof each having a low work function can be used as a material for forming the second electrode 150.

[0363] The second electrode 150 can include at least one selected from 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, and any combination thereof. The second electrode 150 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0364] The second electrode 150 can have a single layer structure or include a multi-layer structure of two or more layers.

[0365] The cover layer

[0366] The first cover layer can be located outside the first electrode 110, and / or the second cover layer can be located outside the second electrode 150. In more detail, the light emitting device 10 can have a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are sequentially stacked in this 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 this 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 this order.

[0367] 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 semi-transmissive electrode or a transmissive electrode, and the first cover layer, and 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 semi-transmissive electrode or a transmissive electrode, and the second cover layer.

[0368] The first cover layer and the second cover layer can increase external light emission efficiency according to the principle of constructive interference. Accordingly, the light emission efficiency of the organic light emitting device 10 is increased, so that the light emission efficiency of the organic light emitting device 10 can be improved.

[0369] Each of the first and second cover layers can include a material having a refractive index (at a wavelength of 589 nm) of 1.6 or greater than 1.6.

[0370] The first and second cover layers can each independently be an organic cover layer including an organic material, an inorganic cover layer including an inorganic material, or a composite cover layer including an organic material and an inorganic material.

[0371] At least one selected from the first and second cover layers can each independently include a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound can be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one selected from the first and second cover layers can each independently include an amine group-containing compound.

[0372] In an embodiment, at least one selected from the first and second cover layers can each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0373] In one or more embodiments, at least one selected from the first and second cover layers can each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:

[0374]

[0375] Electronic device

[0376] The light emitting device can be included in various suitable electronic devices. In an embodiment, the electronic device including the light emitting device can be a light emitting device, a verification device, or the like.

[0377] In addition to the light emitting device, the electronic device (e.g., a light emitting device) can further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer can be located in at least one travel direction of light emitted from the light emitting device. In an embodiment, the light emitted from the light emitting device can be blue light and / or white light. The light emitting device can be the same as described above. In an embodiment, the color conversion layer can include quantum dots. The quantum dots can be, for example, quantum dots as described herein.

[0378] An electronic device can include a first substrate. The first substrate includes a plurality of sub-pixel regions, a color filter includes a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and a color conversion layer can include a plurality of color conversion regions respectively corresponding to the sub-pixel regions.

[0379] A pixel defining film can be between the plurality of sub-pixel regions to define each of the sub-pixel regions.

[0380] The color filter can further include a plurality of color filter regions and a light blocking pattern between the plurality of color filter regions, and the color conversion layer can further include a plurality of color conversion regions and a light blocking pattern between the plurality of color conversion regions.

[0381] The plurality of color filter regions (or the plurality of color conversion regions) can include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, and the first color light, the second color light, and / or the third color light can have different maximum emission wavelengths from each other. In an embodiment, the first color light can be red light, the second color light can be green light, and the third color light can be blue light. In an embodiment, the plurality of color filter regions (or the plurality of color conversion regions) can include quantum dots. In more detail, the first region can include red quantum dots, the second region can include green quantum dots, and the third region can not include quantum dots. The quantum dots are the same as described in this specification. Each of the first region, the second region, and / or the third region can further include a scatterer.

[0382] In an embodiment, the light emitting device can emit a first light, the first region can absorb the first light to emit a first first color light, the second region can absorb the first light to emit a second first color light, and the third region can 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 can have different maximum emission wavelengths from each other. In more detail, the first light can be blue light, the first first color light can be red light, the second first color light can be green light, and the third first color light can be blue light.

[0383] In addition to the light emitting device as described above, the electronic device can further include a thin film transistor. The thin film transistor can include a source electrode, a drain electrode, and an active layer, wherein any one selected from the source electrode and the drain electrode can be electrically coupled to any one selected from the first electrode and the second electrode of the light emitting device.

[0384] The thin film transistor can further include a gate electrode, a gate insulating film, etc.

[0385] The active layer can include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc.

[0386] The electronic device can further include a sealing portion for sealing the light emitting device. The sealing portion can be between the color filter and / or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be guided out to the outside while simultaneously (e.g., concurrently) preventing or reducing penetration of ambient air and / or moisture into the light emitting device. The sealing portion can be a sealing substrate including a transparent glass substrate and / or a plastic substrate. The sealing portion can be a thin film encapsulation layer including at least one of an organic layer and / or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device can be flexible.

[0387] On the sealing portion, various suitable functional layers can be further positioned according to the use of the electronic device in addition to the color filter and / or the color conversion layer. The functional layer can include a touch screen layer, a polarizing layer, etc. The touch screen layer can be a pressure sensitive touch screen layer, a capacitive touch screen layer, and / or an infrared touch screen layer. The authentication device can be, for example, a biometric authentication device for authenticating an individual by using biometric information of a biometric object (e.g., a fingertip, a pupil, etc.).

[0388] The authentication device can further include a biometric information collector in addition to the light emitting device.

[0389] The electronic device can be applied to various suitable displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, and / or endoscope displays), fish finders, various suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), projectors, etc.

[0390] Figure 2 and Figure 3 Description of Drawings

[0391] Figure 2 is a cross-sectional view of a light emitting device according to an embodiment.

[0392] Figure 2 The light emitting device of FIG. 1 includes a substrate 100, a thin film transistor (TFT), a light emitting device, and a sealing portion 300 for sealing the light emitting device.

[0393] The substrate 100 can be a flexible substrate, a glass substrate, and / or a metal substrate. A buffer layer 210 can be on the substrate 100. The buffer layer 210 prevents or reduces penetration of impurities through the substrate 100 and can provide a flat surface on the substrate 100.

[0394] The TFT can be on the buffer layer 210. The TFT can include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0395] The active layer 220 can include inorganic semiconductors (e.g., silicon and / or polysilicon), organic semiconductors, and / or oxide semiconductors, and can include source regions, drain regions, and a channel region.

[0396] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 can be on the active layer 220, and the gate electrode 240 can be on the gate insulating film 230.

[0397] An interlayer insulating film 250 can be on the gate electrode 240. The interlayer insulating film 250 insulates the gate electrode 240 from the source electrode 260 between the gate electrode 240 and the source electrode 260, and insulates the gate electrode 240 from the drain electrode 270 between the gate electrode 240 and the drain electrode 270.

[0398] The source electrode 260 and the drain electrode 270 can be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 can expose the source regions and the drain regions of the active layer 220, and the source electrode 260 and the drain electrode 270 can be in contact (e.g., physical contact) with the exposed portions of the source regions and the drain regions of the active layer 220.

[0399] The TFT can be electrically coupled to the light-emitting device to drive the light-emitting device, and can be covered by a passivation layer 280. The passivation layer 280 can include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting device is provided on the passivation layer 280. The light-emitting device includes the first electrode 110, the intermediate layer 130, and the second electrode 150.

[0400] The first electrode 110 can be on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and can expose a certain area of the drain electrode 270, and the first electrode 110 can be connected to the exposed area of the drain electrode 270.

[0401] A pixel-defining layer 290 including an insulating material can be on the first electrode 110. The pixel-defining layer 290 can expose a certain area of the first electrode 110, and the intermediate layer 130 can be formed in the exposed area of the first electrode 110. The pixel-defining layer 290 can be an organic film based on polyimide and / or polyacryl. In some embodiments, at least some layers of the intermediate layer 130 can extend beyond the upper portion of the pixel-defining layer 290, and can thus be positioned in the form of a common layer.

[0402] The second electrode 150 can be on the intermediate layer 130, and a capping layer 170 can be additionally formed on the second electrode 150. The capping layer 170 can cover the second electrode 150.

[0403] The encapsulation part 300 can be on the cover layer 170. The encapsulation part 300 can be on the light emitting device and protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 can include an inorganic film containing silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide, or a combination thereof; an organic film containing polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyformaldehyde, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE)), or a combination thereof; or a combination of an inorganic film and an organic film.

[0404] Figure 3 is a cross-sectional view illustrating a light emitting apparatus according to an embodiment of the disclosure.

[0405] Figure 3 The light emitting apparatus of Figure 2 is the same as the light emitting apparatus of Figure 3 , but the light blocking pattern 500 and the functional area 400 are additionally on the encapsulation part 300. The functional area 400 can be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In an embodiment, the light emitting device included in the light emitting apparatus of Figure 3 may be a series light emitting device.

[0406] Preparation method

[0407] The layers constituting the hole transport zone, the emission layer, and the layers constituting the electron transport zone can be formed in a certain area by using a suitable method selected from one or more of vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0408] When the layers constituting the hole transport zone, the emission layer, and the layers constituting the electron transport zone are formed by vacuum deposition, the deposition can be performed at a deposition temperature of about 100°C to about 500°C, a vacuum degree of about 10 -8 tor to about 10 -3 tor, and a deposition rate of about / second to about / second, in consideration of the materials to be contained in the layers to be formed and the structure of the layers to be formed.

[0409] Definitions of at least some terms

[0410] The term "C3-C 60A “carbocyclic group” refers to a cyclic group consisting only of carbon and hydrogen and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms), and the term “C1-C 60 A “heterocyclic group” refers to a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 24, or 1 to 18 carbon atoms) and further comprising heteroatoms (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon. C3-C 60 A “carbocyclic group” refers to a cyclic group consisting only of carbon and hydrogen and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms), and the term “C1-C 60 A “heterocyclic group” refers to a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 24, or 1 to 18 carbon atoms) and further comprising heteroatoms (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon. C3-C 60 The number of ring-forming atoms of a “heterocyclic group” can be 3 to 61.

[0411] The term “cyclic group” as used herein includes C3-C 60 A “carbocyclic group” refers to a cyclic group consisting only of carbon and hydrogen and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms), and the term “C1-C 60 A “heterocyclic group” refers to a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 24, or 1 to 18 carbon atoms) and further comprising heteroatoms (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon. C3-C

[0412] The term “π-electron rich C3-C 60 A “cyclic group” refers to a cyclic group having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms) and not comprising a *-N=*’ as a ring-forming moiety, and the term “π-electron deficient C1-C 60 A “cyclic group” refers to a cyclic group having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms) and not comprising a *-N=*’ as a ring-forming moiety, and the term “π-electron deficient C1-C

[0413] For example,

[0414] C3-C 60 A “carbocyclic group” refers to a cyclic group consisting only of carbon and hydrogen and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms), and the term “C1-C A “carbocyclic group” refers to a cyclic group consisting only of carbon and hydrogen and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms), and the term “C1-C

[0415] A “carbocyclic group” refers to a cyclic group consisting only of carbon and hydrogen and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 24, or 3 to 18 carbon atoms), and the term “C1-C 60The heterocyclic group can be i) a group T2, ii) a fused cyclic group in which two or more groups T2are fused (e.g., combined together) with each other, or iii) a fused cyclic group in which at least one group T2and at least one group T1are fused (e.g., combined together) with each other (e.g., a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiophyl group, a benzofuran group, a carbazole group, a dibenzothiophyl group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothienocarbazole group, a benzothiophylcarbazole group, a benzothiophylcarbazole group, a benzoisoindolocarbazole group, a benzoindolocarbazole group, a benzoindolocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiophyl group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthylidine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafuorene group, an azadibenzothiophyl group, an azadibenzothiophene group, and / or an azadibenzofuran group),

[0416] π-electron rich C3-C 60 The cyclic group can be i) a group T1, ii) a fused cyclic group in which two or more groups T1are fused (e.g., combined together) with each other, iii) a group T3, iv) a fused cyclic group in which two or more groups T3are fused (e.g., combined together) with each other, or v) a fused cyclic group in which at least one group T3and at least one group T1are fused (e.g., combined together) with each other (e.g., a C3-C 60Carbocyclic groups, pyrrole groups, thiophene groups, furan groups, indole groups, benzoindole groups, naphthoindole groups, isoindole groups, benzoisoindole groups, naphthoisoindole groups, benzothiophene groups, benzofuran groups, carbazole groups, dibenzothiophene groups, dibenzofuran groups, indole-carbazole groups, indole-carbazole groups, benzofuran-carbazole groups, benzothiophene-carbazole groups, benzothiophene-carbazole groups, benzoindole-carbazole groups, benzocarbazole groups, benzonaphthofuran groups, benzonaphthophene groups, benzonaphthothiophene groups, benzofuran-dibenzofuran groups, benzofuran-dibenzothiophene groups and / or benzothiophene-dibenzothiophene groups),

[0417] C1-C containing nitrogen lacking π electrons 60 The cyclic group can be i) group T4, ii) a fused cyclic group in which two or more groups T4 are fused together (e.g., combined together), iii) a fused cyclic group in which at least one group T4 and at least one group T1 are fused together (e.g., combined together), iv) a fused cyclic group in which at least one group T4 and at least one group T3 are fused together (e.g., combined together), or v) a fused cyclic group in which at least one group T4, at least one group T1, and at least one group T3 are fused together (e.g., combined together) (e.g., pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group). Groups, thiadiazole groups, benzopyrazole groups, benzoimidazolium groups, benzoxazole groups, benzoisoxazole groups, benzothiazole groups, benzoisothiazole groups, pyridine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, benzoisoquinoline groups, quinoxaline groups, benzoquinoxaline groups, quinazoline groups, benzoquinazoline groups, phenanthrene groups, cinnamyl groups, phthalazine groups, naphthidine groups, imidazopyridine groups, imidazopyrimidine groups, imidazotriazine groups, imidazopyrazine groups, imidazopyridazine groups, imidazopyridazine groups, azacarbazole groups, azafluorene groups, azadibenzothiophene groups, azadibenzothiophene groups and / or azadibenzofuran groups),

[0418] Group T1 can be a cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclooctane group, cyclobutene group, cyclopentene group, cyclopentadiene group, cyclohexene group, cyclohexadiene group, cycloheptene group, adamantane group, norbornyl group (or bicyclo[2.2.1]heptane group), norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group and / or phenyl group.

[0419] Group T2may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borol group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, and / or a tetrazine group,

[0420] Group T3may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, and / or a borol group, and

[0421] Group T4may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, and / or a tetrazine group.

[0422] As used herein, the term "cyclic group," "C3-C 60 carbocyclic group," "C1-C 60 heterocyclic group," "π-electron rich C3-C 60 cyclic group," or "π-electron deficient nitrogen containing C1-C 60 cyclic group" refers to a group, a monovalent group, a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) fused (e.g., combined together) with a cyclic group according to the structure of the formula described by the corresponding term. In one or more embodiments, a "phenyl group" can be a benzo group, a phenyl group, a phenylene group, etc., which can be readily understood by one of ordinary skill in the art according to the structure of the formula including the "phenyl group."

[0423] In embodiments, examples of a monovalent C3-C 60 carbocyclic group and a monovalent C1-C 60 heterocyclic group can include a C3-C 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, and examples of a divalent C3-C 60 carbocyclic group and a divalent C1-C 60 heterocyclic group can include a C3-C 10Cycloalkylene groups, C1-C 10 Heterocycloalkylene groups, C3-C 10 Cycloalkenylene groups, C1-C 10 Heterocycloalkenylene groups, C6-C 60 Arylene groups, C1-C 60 Heteroarylene groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heteropolycyclic groups.

[0424] The term “C1-C 60 Alkyl groups” as used herein refers to straight-chain or branched aliphatic hydrocarbon monovalent groups having from 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, a t-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a t-hexyl group, an n-heptyl group, an isohexyl group, a sec-heptyl group, a t-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a t-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a t-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a t-decyl group. In some embodiments, C1-C 60 Alkyl groups” can be C1-C 30 Alkyl groups, C1-C 20 Alkyl groups, or C1-C 10 Alkyl groups. The term “C1-C 60 Alkylene groups” as used herein refers to divalent groups having essentially the same structure as C1-C 60 Alkyl groups.

[0425] The term “C2-C 60 Alkenyl groups” as used herein refers to monovalent hydrocarbon groups having at least one carbon-carbon double bond at the main chain (e.g., middle) or at the terminal (e.g., end) of C2-C 60 Alkyl groups, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. In some embodiments, C2-C 60 Alkenyl groups” can be C2-C 30 Alkenyl groups, C2-C 20 Alkenyl groups, or C2-C 10 Alkenyl groups. The term “C2-C 60 Alkenylene groups” as used herein refers to divalent groups having essentially the same structure as C2-C 60 Alkenyl groups.

[0426] The term “C2-C 60"Alkyne group" refers to the group located at C2-C. 60 The alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., middle) or end (e.g., tip), and examples include ethynyl and propynyl groups. In some embodiments, C2-C 60 The alkynyl group can be C2-C 30 alkynyl group, C2-C 20 alkynyl group or C2-C 10 Alkynyl group. As used in this article, "C2-C" 60 "Imyynyl group" refers to a group that has a C2-C... 60 Alkyne groups are divalent groups with essentially the same structure.

[0427] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 (where A) 101 It is C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy groups, ethoxy groups and isopropoxy groups.

[0428] As used in this article, the term "C3-C" 10 "Cycloalkyl group" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, norbornene alkyl groups (or bicyclic [2.2.1]heptyl groups), bicyclic [1.1.1]pentyl groups, bicyclic [2.1.1]hexyl groups, and bicyclic [2.2.2]octyl groups. As used herein, the term "C3-C..." 10 "Cycloalkylene group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkyl groups are divalent groups with essentially the same structure.

[0429] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl group" refers to a monovalent cyclic group that further comprises at least one heteroatom other than a carbon atom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4 or 5 heteroatoms) as a cyclic atom and has 1 to 10 carbon atoms, and examples include 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. The term "C1-C" as used herein is also used. 10 "Heterocyclic alkyl groups" refers to groups with C1-C2 groups. 10 Heterocyclic alkyl groups are divalent groups with essentially the same structure.

[0430] As used in this article, the term "C3-C" 10Cycloalkenyl groups” means monovalent cyclic groups having 3 to 10 carbon atoms in their ring and at least one carbon-carbon double bond and no aromaticity (e.g., non-aromatic), and examples include cyclopentenyl groups, cyclohexenyl groups, and cycloheptenyl groups. The term “C3-C 10 Cycloalkenyl groups” means monovalent cyclic groups having 3 to 10 carbon atoms in their ring and at least one carbon-carbon double bond and no aromaticity (e.g., non-aromatic), and examples include cyclopentenyl groups, cyclohexenyl groups, and cycloheptenyl groups. The term “C3-C 10 Cycloalkenyl groups” means monovalent cyclic groups having 3 to 10 carbon atoms in their ring and at least one carbon-carbon double bond and no aromaticity (e.g., non-aromatic), and examples include cyclopentenyl groups, cyclohexenyl groups, and cycloheptenyl groups. The term “C3-C

[0431] The term “C1-C 10 Heterocycloalkenyl groups” means monovalent cyclic groups having 1 to 10 carbon atoms in their ring structure, at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon atoms as ring-forming atoms, and at least one double bond. C1-C 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothiophenyl groups. The term “C1-C 10 Heterocycloalkenyl groups” means monovalent cyclic groups having 1 to 10 carbon atoms in their ring structure, at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon atoms as ring-forming atoms, and at least one double bond. C1-C 10 Heterocycloalkenyl groups” means monovalent cyclic groups having 1 to 10 carbon atoms in their ring structure, at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon atoms as ring-forming atoms, and at least one double bond. C1-C

[0432] The term “C6-C 60 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 60 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 60 Examples of aryl groups include fluorenyl groups, phenyl groups, pentalenyl groups, naphthyl groups, azulenyl groups, indacenyl groups, acenaphthylenyl groups, phenalenyl groups, phenanthryl groups, anthryl groups, fluoranthenyl groups, triphenylene groups, pyrenyl groups, Examples of aryl groups include fluorenyl groups, phenyl groups, pentalenyl groups, naphthyl groups, azulenyl groups, indacenyl groups, acenaphthylenyl groups, phenalenyl groups, phenanthryl groups, anthryl groups, fluoranthenyl groups, triphenylene groups, pyrenyl groups, 60 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 30 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 24 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 18 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 60 Aryl groups” means monovalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the term “C6-C 60 When the aryl group and the C6-C

[0433] As used in this article, the term "C1-C" 60 "Heteroaryl group" refers to a monovalent group having a heterocyclic aromatic system containing at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4 or 5 heteroatoms) and 1 to 60 carbon atoms as cyclic atoms. As used herein, the term "C1-C..." 60 A "hybrid aryl group" refers to a divalent group having a heterocyclic aromatic system containing at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms. (C1-C) 60 Examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclophosphine, phenanthrolinel, phthalazinyl, and naphthidyl groups. In some embodiments, C1-C 60 The heteroaryl group can be C1-C 30 heteroaryl groups, C1-C 24 heteroaryl groups or C1-C 18 heteroaryl groups. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the two or more rings may be fused together (e.g., combined together).

[0434] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms, such as 8 to 30 or 8 to 24 carbon atoms) having two or more rings fused together (e.g., combined together), with only carbon atoms as cyclic atoms and lacking aromaticity throughout its molecular structure (e.g., not aromatic when considered as a whole). Examples of monovalent nonaromatic fused polycyclic groups include indenyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, indo[a]phenanthrene groups, and indo[a]anthrayl groups. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused polycyclic group.

[0435] The term "monovalent non-aromatic fused heteropolycyclic group," as used herein, refers to a monovalent group (e.g., having 1 to 60 carbon atoms, such as 1 to 30 or 1 to 24 carbon atoms) that has two or more rings fused (e.g., combined together with one another) to one another, at least one heteroatom (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) in addition to carbon atoms as ring-forming atoms, and is non-aromatic (e.g., not aromatic when considered as a whole) throughout its molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups include pyrrolyl groups, thienyl groups, furanyl groups, indolyl groups, benzoindolyl groups, naphthoindolyl groups, isoindolyl groups, benzoisoindolyl groups, naphthoisoindolyl groups, benzothiopyrrolyl groups, benzothienyl groups, benzofuranyl groups, carbazolyl groups, dibenzothiopyrrolyl groups, dibenzothienyl groups, dibenzofuranyl groups, azacarbazolyl groups, azafuorenyl groups, azadibenzothiopyrrolyl groups, azadibenzothienyl groups, azadibenzofuranyl groups, pyrazolyl groups, imidazolyl groups, triazolyl groups, tetrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzopyrazolyl groups, benzimidazolyl groups, benzoxazolyl groups, benzothiazolyl groups, benzoxadiazolyl groups, benzothiadiazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, imidazotriazinyl groups, imidazopyrazinyl groups, imidazopyridazinyl groups, indenocarbazolyl groups, indolocarbazolyl groups, benzofuranocarbazolyl groups, benzothienocarbazolyl groups, benzothiopyrrolocarbazolyl groups, benzoindolocarbazolyl groups, benzo carbazolyl groups, benzonaphthofuranyl groups, benzonaphthothienyl groups, benzonaphthothiopyrrolyl groups, benzofuranodibenzofuranyl groups, benzofuranodibenzothienyl groups, and benzothienodibenzothienyl groups. The term "divalent non-aromatic fused heteropolycyclic group," as used herein, refers to a divalent group having essentially the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0436] The term "C6-C 60 aryloxy group," as used herein, refers to -OA 102 (where A 102 is a C6-C 60 aryl group), and the term "C6-C 60 arylthio group," as used herein, refers to -SA 103 (where A 103 is a C6-C 60 aryl group).

[0437] The term "R 10a ," as used herein, refers to:

[0438] deuterium (-D), -F, -CI, -Br, -I, a hydroxyl group, a cyano group, or a nitro group;

[0439] each unsubstituted or substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 carbon ring group, a C1-C 60 hetero ring group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=0)(Q 11 ), -S(=0)2(Q 11 ), -P(=0)(Q 11 )(Q 12 ), or any combination thereof; 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, or a C1-C 60 alkoxy group;

[0440] each unsubstituted or substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 60 carbon ring group, a C1-C 60 hetero ring group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=0)(Q 21 ), -S(=0)2(Q 21 ), -P(=0)(Q 21 )(Q 22 ), or any combination thereof; 60 carbon ring group, a C1-C60 heterocyclyl group, C6-C 60 aryloxy group, or C6-C 60 arylthio group; or

[0441] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 ).

[0442] As used herein, Q1to Q3, Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; a C1-C 60 alkyl group; a C2-C 60 alkenyl group; a C2-C 60 alkynyl group; a C1-C 60 alkoxy group; or a C3-C 60 carbocyclic group or C1-C 60 heterocyclic group, each unsubstituted or substituted with deuterium, -F, a cyano group, a C1-C 60 alkyl group, a C1-C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

[0443] As used herein, the term "heteroatom" means any atom other than a carbon atom and a hydrogen atom. Examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, and any combination thereof.

[0444] As used herein, the term "Ph" means a phenyl group, as used herein the term "Me" means a methyl group, as used herein the term "Et" means an ethyl group, as used herein the term "tert-Bu" or "Bu t " means a tert-butyl group, and as used herein the term "OMe" means a methoxy group.

[0445] As used herein, the term "biphenyl group" means a "phenyl group substituted with a phenyl group." In other words, a "biphenyl group" is a C6-C60 a substituted phenyl group having an aryl group as a substituent.

[0446] As used herein, the term "triphenyl group" refers to a "phenyl group substituted with a biphenyl group". In other words, a "triphenyl group" is a C6-C 60 a C6-C 60 a substituted phenyl group having an aryl group as a substituent.

[0447] Unless otherwise defined, each of and refers to the point of attachment to the adjacent atom in the corresponding formula, as used herein.

[0448] Hereinafter, the compounds according to the embodiments and the organic light emitting device according to the embodiments will be described in more detail with reference to synthesis examples and examples. The expression "use B instead of A" used for describing the synthesis examples means using an equimolar equivalent of B instead of A.

[0449] Synthesis Example

[0450] Synthesis Example 1: Synthesis of Compound 1

[0451]

[0452] 1) Synthesis of Intermediate [1-A]

[0453] Add 8.3 g (50 mmol) of 2'-nitroacetophenone and 4.7 g (150 mmol) of methylamine to a reaction vessel coupled to a Dean-Stark trap, and suspend in 250 ml of toluene. Increase the reaction temperature to 110°C, and stir the resulting mixture for 24 hours. After completion of the reaction, cool the mixture at room temperature, and remove the solvent therefrom, to obtain 8.2 g (46 mmol) of the target compound (Intermediate [1-A]).

[0454] 2) Synthesis of Intermediate [1-B]

[0455] Add 8.2 g (46 mmol) of Intermediate [1-A] to a reaction vessel, and suspend in 100 ml of tetrahydrofuran. Slowly add 17 ml of a methylmagnesium bromide solution (3.0 M in diethyl ether) thereto at -78°C. Increase the reaction temperature to room temperature, and stir the resulting mixture for 24 hours. After completion of the reaction, add 200 ml of distilled water thereto, and subject to an extraction process using ethyl acetate. Wash the extracted organic layer with a saturated aqueous sodium chloride solution and dry by using sodium sulfate. Separate the residue obtained by removing the solvent therefrom by column chromatography, to obtain 7.4 g (38 mmol) of the target compound (Intermediate [1-B]).

[0456] 3) Synthesis of Intermediate [1-C]

[0457] To a reaction vessel were added 7.4 g (38 mmol) of Intermediate [1-B], 15.8 g (133 mmol) of tin, and 21.8 g (209 mmol) of a 35 wt% solution of HC1, suspended in 380 ml of ethanol. The reaction temperature was raised to 80°C, and the resulting mixture was stirred for 12 hours. After completion of the reaction, the reaction product was cooled at room temperature, and then neutralized using a saturated aqueous sodium bicarbonate solution. Extraction was performed using ethyl acetate, and the extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography, thereby obtaining 5.6 g (34 mmol) of the target compound (Intermediate [1-C]).

[0458] 4) Synthesis of Intermediate [1-D]

[0459] To a reaction vessel were added 5.6 g (34 mmol) of Intermediate [1-C], 6.7 g (38 mmol) of 3-bromofluorobenzene, 920 mg (1.0 mmol) of tris(dibenzylideneacetone)dipalladium(0), 700 mg (1.7 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 6.6 g (68 mmol) of sodium tert-butoxide, and suspended in 340 ml of toluene. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 12 hours. After completion of the reaction, the reaction product was cooled at room temperature, 200 ml of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography, thereby obtaining 6.5 g (25 mmol) of the target compound (Intermediate [1-D]).

[0460] 5) Synthesis of Intermediate [1-E]

[0461] To a reaction vessel were added 6.5 g (25 mmol) of intermediate [1-D], 8.0 g (20 mmol) of 3-(1H-imidazol-1-yl)phenol, and 8.5 g (40 mmol) of potassium phosphate, and suspended in 200 ml of dimethylformamide. The resulting reaction mixture was heated and stirred at a temperature of 160°C for 12 hours. After completion of the reaction, the reaction product was cooled at room temperature, 200 ml of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography, thereby obtaining 6.8 g (17 mmol) of the target compound (Intermediate [1-E]).

[0462] 6) Synthesis of Intermediate [1-F]

[0463] To a reaction vessel were added 6.8 g (17 mmol) of intermediate [1-E], 125 ml (850 mmol) of triethyl orthoformate, and 9.7 g (94 mmol) of HCl 35 wt% solution, heated, and then stirred at 80°C for 12 hours. After completion of the reaction, the resulting mixture was cooled at room temperature, and the residue obtained by removing the solvent therefrom was separated by column chromatography, thereby obtaining 5.8 g (13 mmol) of the target compound (Intermediate [1-F]).

[0464] 7) Synthesis of Intermediate [1-G]

[0465] To a reaction vessel were added 5.8 g (13 mmol) of intermediate [1-F] and 5.5 g (39 mmol) of iodomethane, and suspended in 130 ml of toluene. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 12 hours. After completion of the reaction, the reaction product was cooled at room temperature to remove a part of the solvent, and then distilled water was added thereto to filter out the resulting solid. The filtered solid was purified using a recrystallization method, thereby obtaining 5.3 g (9.0 mmol) of the target compound (Intermediate [1-G]).

[0466] 8) Synthesis of Intermediate [1-H]

[0467] To a reaction vessel were added 5.3 g (9.0 mmol) of intermediate [1-G] and 4.4 g (27 mmol) of ammonium hexafluorophosphate, and suspended in a solution containing methanol and water at a ratio of 2:1. The resulting reaction mixture was stirred at room temperature for 12 hours. The resulting solid was filtered out and purified using a recrystallization method, thereby obtaining 4.4 g (6.1 mmol) of the target compound (Intermediate [1-H]).

[0468] 9) Synthesis of Compound 1

[0469] Intermediate [1-H] (4.4 g, 6.1 mmol), dichloro(l,5-cyclooctadiene) platinum (2.5 g, 6.7 mmol), and sodium acetate (1.0 g, 12.2 mmol) were suspended in 240 ml of dioxane. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 72 hours. After completion of the reaction, the reaction product was cooled at room temperature, 220 ml of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography, thereby obtaining 430 mg (0.7 mmol) of the target compound (Compound 1).

[0470] Synthesis Example 2: Synthesis of Compound 7

[0471]

[0472] 1) Synthesis of Intermediate [7-A]

[0473] Intermediate [1-F] (5.8 g, 13 mmol) and ammonium hexafluorophosphate (4.2 g, 26 mmol) were added to a reaction vessel and suspended in a solution containing methanol and water at a ratio of 2:1. The resulting reaction mixture was stirred at room temperature for 12 hours. The resulting solid was filtered out and separated by column chromatography, thereby obtaining 6.7 g (12 mmol) of the target compound (Intermediate [7-A]).

[0474] 2) Synthesis of Intermediate [7-B]

[0475] Intermediate [7-A] (6.7 g, 12 mmol), diphenyl iodonium hexafluorophosphate (5.5 g, 13 mmol), and copper acetate (110 mg, 0.6 mmol) were suspended in 240 ml of dimethylformamide. The resulting reaction mixture was heated and stirred at a temperature of 120°C for 12 hours. After completion of the reaction, the reaction product was cooled at room temperature, 220 ml of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated using a recrystallization method, thereby obtaining 5.4 g (7.0 mmol) of the target compound (Intermediate [7-B]).

[0476] 3) Synthesis of Compound 7

[0477] Synthesis Example 3: Synthesis of Compound 21

[0478] Synthesis Example 3: Synthesis of Compound 21

[0479]

[0480] Synthesis Example 3: Synthesis of Compound 21

[0481] Synthesis Example 4: Synthesis of Compound 32

[0482]

[0483] 1) Synthesis of Intermediate [32-A]

[0484] Synthesis Example 4: Synthesis of Compound 32

[0485] 2) Synthesis of Intermediate [32-B]

[0486] Synthesis Example 4: Synthesis of compound 32

[0487] 3) Synthesis of intermediate [32-C]

[0488] Synthesis Example 4: Synthesis of compound 32

[0489] 4) Synthesis of compound 32

[0490] Synthesis Example 4: Synthesis of compound 32

[0491] Synthesis Example 5: Synthesis of compound 41

[0492]

[0493] Synthesis Example 4: Synthesis of compound 32

[0494] Synthesis Example 6: Synthesis of compound 47

[0495]

[0496] Compound 47 was obtained in substantially the same manner as in Synthesis Example 1, except that 3-(1H-tetrazol-1-yl)phenol was used instead of 3-(1H-imidazol-1-yl)phenol. Thus, in the synthesis of Compound 47, Intermediate [47-A] through Intermediate [47-D] were used instead of Intermediate [1-E] through Intermediate [1-H].

[0497] Synthesis Example 7: Synthesis of Compound 61

[0498]

[0499] Compound 61 was obtained in substantially the same manner as in Synthesis Example 1, except that 1-bromo-3-fluoro-5-(tert-butyl)benzene was used instead of 3-bromo fluorobenzene. Thus, in the synthesis of Compound 61, Intermediate [61-D] through Intermediate [61-H] were used instead of Intermediate [1-D] through Intermediate [1-H].

[0500] Synthesis Example 8: Synthesis of Compound 99

[0501]

[0502] 1) Synthesis of Intermediate [99-A]

[0503] To a reaction vessel were added 4.7 g (50 mmol) of aniline, 22.3 g (100 mmol) of 1-(3-bromophenyl)-1H-imidazole, 1.1 g (1.2 mmol) of tris(dibenzylideneacetone)dipalladium(0), 820 mg (2.0 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, and 9.7 g (100 mmol) of sodium tert-butoxide and suspended in 500 ml of toluene. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 3 hours. After completion of the reaction, the reaction product was cooled at room temperature, 250 ml of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography, thereby obtaining 8.2 g (35 mmol) of the target compound (Intermediate [99-A]).

[0504] 2) Synthesis of Intermediate [99-B]

[0505] To a reaction vessel were added 8.2 g (35 mmol) of intermediate [99-A], 16.5 g (70 mmol) of 1,3-dibromobenzene, 1.0 g (1.1 mmol) of tris(dibenzylideneacetone)dipalladium(0), 740 mg (1.8 mmol) of 2-dicyclohexylphosphino-2',6'-dimehtoxybiphenyl, and 6.8 g (70 mmol) of sodium tert-butoxide, and suspended in 350 mL of toluene. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 3 hours. After completion of the reaction, the reaction product was cooled at room temperature, 180 mL of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 10.5 g (27 mmol) of the target compound (Intermediate [99-B]).

[0506] 3) Synthesis of Intermediate [99-C]

[0507] To a reaction vessel were added 10.5 g (27 mmol) of intermediate [99-B], 3.0 g (18 mmol) of intermediate [1-C], 450 mg (0.5 mmol) of tris(dibenzylideneacetone)dipalladium(0), 370 mg (0.9 mmol) of 2-dicyclohexylphosphino-2',6'-dimehtoxybiphenyl, and 3.5 g (36 mmol) of sodium tert-butoxide, and suspended in 180 mL of toluene. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 3 hours. After completion of the reaction, the reaction product was cooled at room temperature, 90 mL of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 6.2 g (13 mmol) of the target compound (Intermediate [99-C]).

[0508] 4) Synthesis of Intermediate [99-D]

[0509] To a reaction vessel were added 6.2 g (13 mmol) of intermediate [99-C], 96 mL (650 mmol) of triethyl orthoformate, and 7.4 g (72 mmol) of HCl 35 wt% solution, heated, and then stirred at 80°C for 12 hours. After completion of the reaction, the resulting mixture was cooled at room temperature, and the residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 5.2 g (10 mmol) of the target compound (Intermediate [99-D]).

[0510] 5) Synthesis of Intermediate [99-E]

[0511] To a reaction vessel were added 5.2 g (10 mmol) of intermediate [99-D] and 4.2 g (30 mmol) of methyl iodide and suspended in 100 ml of toluene. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 12 hours. After completion of the reaction, the reaction product was cooled at room temperature to remove a portion of the solvent, and then distilled water was added thereto to filter out the resulting solid. The filtered solid was purified using a recrystallization method to obtain 5.6 g (8.4 mmol) of the target compound (intermediate [99-E]).

[0512] 6) Synthesis of intermediate [99-F]

[0513] To a reaction vessel were added 5.6 g (8.4 mmol) of intermediate [99-E] and 4.1 g (25 mmol) of ammonium hexafluorophosphate and suspended in a solution containing methanol and water in a ratio of 2:1.

[0514] The resulting reaction mixture was stirred at room temperature for 12 hours. The resulting solid was filtered out and purified using a recrystallization method to obtain 5.2 g (6.6 mmol) of the target compound (intermediate [99-F]).

[0515] 7) Synthesis of compound 99

[0516] To a reaction vessel were added 5.2 g (6.6 mmol) of intermediate [99-F], 2.7 g (6.9 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 1.1 g (13.2 mmol) of sodium acetate and suspended in 260 ml of dioxane. The resulting reaction mixture was heated and stirred at a temperature of 110°C for 72 hours. After completion of the reaction, the reaction product was cooled at room temperature, 260 ml of distilled water was added thereto, and extraction was performed using ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried by using sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 410 mg (0.6 mmol) of the target compound (compound 99).

[0517] Properties of the compounds synthesized according to Synthesis Example 1 to Synthesis Example 8 1 H NMR and MS / FAB are shown in Table 1 below.

[0518] By referring to the above synthesis routes and source materials, one of ordinary skill in the art can easily recognize compounds other than the compounds shown in Table 1.

[0519] Table 1

[0520]

[0521]

[0522] Example

[0523] Example 1

[0524] As a substrate and an anode, a glass substrate having 15 Ωcm 2 The ITO-coated glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, cleaned by ultrasonic treatment using isopropyl alcohol and pure water each for 5 minutes, and then by ultraviolet irradiation and exposure to ozone for 30 minutes. Then, the glass substrate was loaded onto a vacuum deposition apparatus.

[0525] 2-TNATA was vacuum-deposited on the ITO anode formed on the glass substrate to form a hole injection layer having a thickness of 50 nm, and then NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 30 nm. mCBP as a host and Compound 1 as a dopant were co-deposited on the hole transport layer in a weight ratio of 90:10 to form an emission layer having a thickness of 20 nm.

[0526] Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was deposited on the emission layer to form a hole blocking layer having a thickness of 10 nm, Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 40 nm, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 100 nm, thereby completing the manufacture of the organic light-emitting device.

[0527]

[0528]

[0529] Examples 2 to 8 and Comparative Examples 1 and 2

[0530] The organic light-emitting device was manufactured in substantially the same manner as in Example 1, but in forming the emission layer, the respective compounds shown in Table 2 were used instead of Compound 1 as a dopant.

[0531] Evaluation Example 1

[0532] ​​​​​​​The driving voltage, current density, luminance, luminous efficiency, emission color, and maximum emission wavelength of the organic light emitting devices manufactured according to Examples 1 to 8 and Comparative Examples 1 and 2 were measured using a Keithley SMU 236 and a luminance meter PR650, and the results thereof are shown in Table 2.

[0533] Table 2

[0534]

[0535]

[0536]

[0537] Referring to Table 2, it can be seen that the organic light emitting devices of Examples 1 to 8 have low driving voltage, high luminance, and high luminous efficiency, compared to the organic light emitting devices of Comparative Examples 1 and 2.

[0538] An organic light emitting device including the organic metal compound can have low driving voltage, high luminance, and high luminous efficiency.

[0539] It is to be understood that the embodiments described herein are to be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as being applicable to other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details can be made therein without departing from the spirit and scope of the disclosure as defined by the following claims and their equivalents.

Claims

1.A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emission layer, wherein the light-emitting device contains at least one organometallic compound represented by Formula 1: Formula 1 wherein, in Formula 1, M1 is Pt, Y1 and Y2 are each independently C, T1 to T4 are each independently a bond, wherein, when T1 is a bond, Y1 and M1 are directly bonded to each other, when T2 is a bond, Y2 and M1 are directly bonded to each other, when T3 is a bond, C in ring A1 is directly bonded to M1, and when T4 is a bond, C in ring A2 is directly bonded to M1, two of the bonds between Y1 and M1, between Y2 and M1, between C in ring A1 and M1, and between C in ring A2 and M1 are each a coordination bond, and the remaining two bonds are each a covalent bond, L1 and L3 are each independently a single bond, X1is C(R1) or N, X2is C(R2) or N, and X 11 is C(R5)(R6), Ring A 11 and Ring A 12 each independently is a phenyl group, a1 to a3 are each independently 1, L2is selected from -N(R9)- '、 -S- ' and -O- ' ring A1-R7 is a group represented by one of Formula 2-1 and Formula 2-2, and ring A2-R8 is a group represented by Formula 2-4: wherein, in Formula 2-1, Formula 2-2, and Formula 2-4, b11 and b12 are each independently an integer of 0 to 3, X1, X2, X 11 As defined above in formula 1, and Ring A 13 and Ring A 14 each independently is a phenyl group, In Equations 1, 2-1, 2-2, and 2-4, R5, R6, and R8 are each independently C1-C. 10 Alkyl groups, and R1, R2, R7 and R9 to R 14 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or substituted with at least one R 10a Replacement C1-C 20 alkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 18 Carbocyclic groups and unsubstituted or substituted groups with at least one R 10a Replacement C1-C 18 Heterocyclic groups, b13 and b14 are each independently an integer of 0 to 4, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; or and each represents a site of attachment to an adjacent atom, and R 10a is: 2.The light-emitting device of claim 1, wherein the intermediate layer further includes a hole transport zone between the first electrode and the emission layer, and an electron transport zone between the emission layer and the second electrode, each C1-C4alkyl group is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 10 each C1-C4alkyl group is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 10 each C1-C4alkoxy group is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or the hole transport zone includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport zone includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof. 3.The light-emitting device of claim 1, wherein the emission layer contains the at least one organometallic compound represented by Formula 1. 4.The light-emitting device of claim 3, wherein the emission layer further contains a host, and an amount of the at least one organometallic compound represented by Formula 1 is 0.01 parts by weight to 49.99 parts by weight, based on 100 parts by weight of the emission layer. 5.The light-emitting device of claim 4, wherein the host includes a silicon-containing compound, a phosphine oxide-containing compound, or any combination thereof. 6.The light-emitting device of claim 3, wherein the emission layer emits blue light having a maximum emission wavelength of 410 nm to 500 nm. 7.The light-emitting device of claim 2, wherein the electron transport zone contains a phosphine oxide-containing compound, a silyl compound, or any combination thereof. 8.An electronic device comprising the light-emitting device of any one of claims 1 to 7. 9.The electronic device of claim 8, further comprising a thin film transistor, wherein the thin film transistor includes a source electrode and a drain electrode, and ​ The first electrode of the light emitting device is electrically coupled to at least one selected from the source electrode and the drain electrode of the thin film transistor. 10.The electronic device of claim 8, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. 11.An organometallic compound represented by Formula 1: Formula 1 wherein In Formula 1, M1 is Pt, Y1 and Y2 are each independently C, T1 to T4 are each independently a bond, wherein, when T1 is a bond, Y1 and M1 are directly bonded to each other, when T2 is a bond, Y2 and M1 are directly bonded to each other, when T3 is a bond, C in ring A1 is directly bonded to M1, and when T4 is a bond, C in ring A2 is directly bonded to M1, two of the bonds between Y1 and M1, between Y2 and M1, between C in ring A1 and M1, and between C in ring A2 and M1 are each a coordination bond, and the remaining two bonds are each a covalent bond, X1is C(R1) or N, X2is C(R2) or N, and X 11 is C(R5)(R6), Ring A 11 and Ring A 12 each independently is a phenyl group, L1 and L3 are each independently a single bond, L2is selected from -N(R9)- '、 -S- ' and -O- ' a1 to a3 are each independently 1, ring A1-R7 is a group represented by one of Formula 2-1 and Formula 2-2, and ring A2-R8 is a group represented by Formula 2-4: wherein, in Formula 2-1, Formula 2-2, and 2-4, X1, X2, X 11 As defined above in formula 1, and Ring A 13 and Ring A 14 each independently is a phenyl group, In Equations 1, 2-1, 2-2, and 2-4, R5, R6, and R8 are each independently C1-C. 10 Alkyl groups, and R1, R2, R7, R9 to R 14 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or substituted with at least one R 10a Replacement C1-C 20 alkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 18 Carbocyclic groups and unsubstituted or substituted groups with at least one R 10a Replacement C1-C 18 Heterocyclic groups, b11 and b12 are each independently an integer of 0 to 3, b13 and b14 are each independently an integer of 0 to 4, and each represents a site of attachment to an adjacent atom, and R 10a is: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; or each C1-C4alkyl group is optionally substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 10 each C1-C4alkyl group is optionally substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 10 each C1-C4alkyl group is optionally substituted with deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, or any combination thereof; 12.The organometallic compound of claim 11, wherein R1, R2, R7, R9 to R 14 each independently selected from the group consisting of: hydrogen, deuterium, -F, -CI, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 20 alkyl group and a C1-C 20 alkoxy group; Each is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 10 alkyl groups and C1-C 10 At least one substituted C1-C alkoxy group 20 alkyl groups and C1-C 20 Alkoxy group; a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a cinnolinyl group, a triazinyl group, a pyrrolopyrrolopyridyl group, and a dihydro-pyranoindolyl group; and Each is selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 10 alkyl groups and C1-C 10 At least one substituted cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, norbornenyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, indole group, isoindoleyl group, indazole group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphineyl group, triazineyl group, pyridopyrrolopyridyl group, and dihydropyranoindoleyl group. 13.The organometallic compound of claim 11, wherein the organometallic compound represented by Formula 1 is selected from the following compounds: 。

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