Organic metal compound and organic light-emitting device comprising the same

Abstract

An organic light-emitting device and an organic metal compound are provided. The organic light-emitting device includes a first electrode, a second electrode facing the first electrode, an organic layer located between the first electrode and the second electrode and including an emission layer, and at least one organic metal compound represented by Formula 1: <Formula 1> #imgabs0# wherein M 11 , Ring A 11 To Ring A 15 , Y 11 To Y 14 , B 11 To B 14 , L 1 To L 3 、a1 to a3、X 1 and X 2 , R 11 To R 15 , b11 to b15 are the same as defined in the specification.

Description

[0001] Korean Patent Application No. 10-2018-0166415, filed on December 20, 2018 in the Korean Intellectual Property Office, and entitled “Organometallic Compound and Organic Light-Emitting Device Including the Same” is hereby incorporated by reference in its entirety. Technical Field

[0002] Embodiments relate to an organometallic compound and an organic light emitting device including the organometallic compound. Background Art

[0003] Organic light emitting devices are self-emissive devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art.

[0004] An example of such an organic light-emitting device may include a first electrode disposed on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transfer from an excited state to a ground state, thereby generating light. Summary of the invention

[0005] Embodiments relate to an organic light-emitting device including a first electrode, a second electrode facing the first electrode, an organic layer located between the first electrode and the second electrode and including an emission layer, and at least one organic metal compound represented by Formula 1:

[0006] <Formula 1>

[0007]

[0008] In formula 1,

[0009] M 11 can be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm),

[0010] Ring A 11 To Ring A 15 can be independently selected from C 5 -C60 Carbocyclic and C 1 -C 60 Heterocyclic group,

[0011] Y 11 To Y 14 may be independently selected from carbon atoms (C) and nitrogen atoms (N),

[0012] B 11 To B 14 may be independently selected from a single bond, O and S,

[0013] L 1 To L 3 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*'、*-C(R 16 )=*'、*=C(R 16 )-*'、*-C(R 16 )=C(R 17 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*'、*-N(R 16 )-*'、*-P(R 16 )-*'、*-Si(R 16 )(R 17 )-*' and *-Ge(R 16 )(R 17 )-*',

[0014] a1 to a3 may be independently selected from 0, 1, 2 and 3, wherein at least two selected from a1 to a3 may be independently selected from 1, 2 and 3. When a1 is 0, ring A 11 and Ring A 12 It can be disconnected. When a2 is 0, ring A 13 and Ring A 14 It can be disconnected. When a3 is 0, ring A 11 and Ring A 14 You can not connect,

[0015] X 1 and X 2 may be independently selected from O and S,

[0016] R 11 To R 17 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),

[0017] R 16 and R 11 , R 16 and R 12 , R 16 and R 13 and / or R 16 and R 14 Can be optionally linked to form a substituted or unsubstituted C 5 -C 60Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0018] b11 to b15 may each independently be an integer from 1 to 10,

[0019] Substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

[0020] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0021] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0022] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;

[0023] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0024] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0025] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group,

[0026] * and *' both represent the binding sites with adjacent atoms, and

[0027] B represents a boron atom.

[0028] Embodiments also relate to an organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Features will become apparent to those skilled in the art by describing example embodiments in detail with reference to the accompanying drawings, in which:

[0030] Figures 1 to 4 A schematic diagram of an organic light emitting device according to example embodiments is shown. DETAILED DESCRIPTION

[0031] Now, example embodiments will be described more fully below with reference to the accompanying drawings; however, they may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. On the contrary, these embodiments are provided so that the present disclosure will be thorough and complete, and the example implementations will be fully conveyed to those skilled in the art. In the accompanying drawings, the sizes of layers and regions may be exaggerated for clarity of illustration. The same reference numerals always refer to the same elements. As used herein, the term "and / or" includes any and all combinations of one or more related listed items. When a statement such as "at least one (kind / person) of ... " follows a column of elements (elements), the elements (elements) of the entire column are modified, rather than modifying the individual elements (elements) in the column.

[0032] The organometallic compound according to the example embodiment is represented by Formula 1:

[0033] <Formula 1>

[0034]

[0035] In Formula 1, B represents a boron atom.

[0036] In formula 1, M 11 It can be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).

[0037] In an example embodiment, M 11 It can be selected from Pt, Pd, Cu, Ag and Au.

[0038] In Formula 1, Ring A 11 To Ring A 15 can be independently selected from C 5 -C 60 Carbocyclic and C 1 -C 60 Heterocyclic group.

[0039] In an exemplary embodiment, ring A 11 To Ring A 15 can be independently selected from benzene, naphthalene, anthracene, phenanthrene, azulene, benzo[9,10]phenanthrene, pyrene, Cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, furan, thiophene, silole, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilole, dibenzosilole, indenopyridine, indolepyridine, benzofuranopyridine, benzothienopyridine, benzothiorrolopyridine, indenopyrimidine, indolepyrimidine, benzofuranopyrimidine, benzothienopyrimidine, benzothiorrolopyrimidine, dihydropyridine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline , pyrrole, pyrazole, imidazole, 2,3-dihydroimidazole, triazole, 2,3-dihydrotriazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, 2,3-dihydrobenzimidazole, imidazopyridine, 2,3-dihydroimidazopyridine, imidazopyrimidine, 2,3-dihydroimidazopyrimidine, imidazopyrazine, 2,3-dihydroimidazopyrazine, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

[0040] In an exemplary embodiment, ring A 11 and Ring A 14 Each may be independently selected from the groups represented by Formula 2-1(1) to Formula 2-1(27) and Formula 2-2(1) to Formula 2-2(20):

[0041]

[0042]

[0043]

[0044] In Formula 2-1(1) to Formula 2-1(27) and Formula 2-2(1) to Formula 2-2(20),

[0045] Y 15 It can be Y of formula 1 11 or Y 14 ,

[0046] X 21 Can be N or C (R 21 ), X 22 Can be N or C (R 22 ), X 23 Can be N or C (R 23 ), X 24 Can be N or C (R 24 ), X 25 Can be N or C (R 25 ), X 26 Can be N or C (R 26 ), X 27 Can be N or C (R27 ), X 28 Can be N or C (R 28 ),

[0047] X 29 It can be C(R 29a )(R 29b )、N(R 29 )、O、S or Si(R 29a )(R 29b ),

[0048] R 21 To R 29 and R 25a To R 29b can be independently combined with R in formula 1 11 and R 14 Same as described,

[0049] * indicates the same as B in formula 1 11 or B 14 The binding position of

[0050] *' represents the same as (L 1 ) a1 or (L 2 ) a2 The binding site of

[0051] *" indicates the same as (L 3 ) a3 The combination position.

[0052] In an exemplary embodiment, ring A 11 and Ring A 14 Each may be independently selected from the groups represented by Formula 3-1(1) to Formula 3-1(38) and Formula 3-2(1) to Formula 3-2(23):

[0053]

[0054]

[0055]

[0056] In Formula 3-1(1) to Formula 3-1(38) and Formula 3-2(1) to Formula 3-2(23),

[0057] Y 15 It can be Y of formula 1 11 or Y 14 ,

[0058] X 29 It can be C(R 29a )(R 29b )、N(R29 )、O、S or Si(R 29a )(R 29b ),

[0059] R 29 , R 29a , R 29b , R 31 and R 32 can be independently combined with R in formula 1 11 and R 14 Same as described,

[0060] b32 can be 1 or 2,

[0061] b33 can be 1, 2 or 3,

[0062] b34 can be 1, 2, 3 or 4,

[0063] b35 can be 1, 2, 3, 4 or 5,

[0064] b36 can be 1, 2, 3, 4, 5, or 6,

[0065] * indicates the same as B in formula 1 11 or B 14 The binding position of

[0066] *' represents the same as (L 1 ) a1 or (L 2 ) a2 The binding site of

[0067] *" indicates the same as (L 3 ) a3 The combination position.

[0068] In one embodiment, in Formula 3-1(1) to Formula 3-1(38) and Formula 3-2(1) to Formula 3-2(23), R 29 , R 29a , R 29b , R 31 and R 32 Can be independently selected from:

[0069] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0070] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl. 1 -C 20 Alkyl and C1 -C 20 Alkoxy;

[0071] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl, and triazinyl; and

[0072] The phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, phenanthryl groups, anthracenyl groups, pyridyl groups, pyrimidinyl groups, carbazolyl groups and triazine groups are all substituted with at least one group selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl group, terphenyl group, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, phenanthryl groups, anthracenyl groups, pyridyl groups, pyrimidinyl groups, carbazolyl groups and triazine groups.

[0073] In an exemplary embodiment, in Equations 3-1(1) to 3-1(38) and 3-2(1) to 3-2(23), when R 29 , R 29a , R 29b , multiple R 31 and multiple R 32 At least one of the following is selected from: C 1 -C 20 Alkyl; and C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl 1 -C 20 When the alkyl group is an alkyl group, the organometallic compound represented by Formula 1 may have stable optical and electrical properties.

[0074] In an exemplary embodiment, in Equations 3-1(1) to 3-1(38) and 3-2(1) to 3-2(23), when R 29 , R 29a , R 29b , multiple R 31 and multiple R 32 When at least one of the selected ones is selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl and triazine, the organic metal compound represented by Formula 1 can prevent the formation of an excited complex by including a bulky substituent.

[0075] In example embodiments, in Formulas 3-1(1) to 3-1(38) and 3-2(1) to 3-2(23), R 29 , R 29a , R 29b , R 31 and R 32 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, -CD 3, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and phenyl.

[0076] In the exemplary embodiment, when the 29 , R 29a , R 29b , multiple R 31 and multiple R 32 At least one of the selected is methyl or -CD 3 When , the organometallic compound represented by Formula 1 may have stable optical and electrical properties.

[0077] In the exemplary embodiment, when the 29 , R 29a , R 29b , multiple R 31 and multiple R 32 When at least one selected from among is a phenyl group, the organometallic compound represented by Formula 1 may prevent the formation of an exciplex by including a bulky substituent.

[0078] In an exemplary embodiment, ring A 11 and Ring A 14 They may be independently selected from the groups represented by Formula 3-1(1), Formula 3-1(28), Formula 3-1(31), and Formula 3-1(36) to Formula 3-1(38).

[0079] In an exemplary embodiment, in Formula 1, Ring A 12 , Ring A 13 and Ring A 15 Each of the compounds may be independently selected from benzene, pyridine, pyridazine, quinoline, isoquinoline, quinoxaline, quinazoline, indole, carbazole, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilole and dibenzosilole.

[0080] In formula 1, Y 11 To Y 14 They may be independently selected from carbon atoms (C) and nitrogen atoms (N).

[0081] In an exemplary embodiment, in Formula 1,

[0082] Y 11 To Y 14 Can all be C;

[0083] Y 11 To Y 13 Can be C, Y 14 Can be N;

[0084] Y 11 , Y 12 and Y 14 Can be C, Y 13Can be N;

[0085] Y 11 , Y 13 and Y 14 Can be C, Y 12 Can be N;

[0086] Y 12 To Y 14 Can be C, Y 11 Can be N;

[0087] Y 11 and Y 12 Can be C, Y 13 and Y 14 Can all be N;

[0088] Y 11 and Y 13 Can be C, Y 12 and Y 14 Can all be N;

[0089] Y 11 and Y 14 Can be C, Y 12 and Y 13 Can all be N;

[0090] Y 12 and Y 13 Can be C, Y 11 and Y 14 Can all be N;

[0091] Y 12 and Y 14 Can be C, Y 11 and Y 13 Can be all N; or

[0092] Y 13 and Y 14 Can be C, Y 11 and Y 12 Both can be N.

[0093] In an exemplary embodiment, in Formula 1,

[0094] Y 11 To Y 14 Can all be C;

[0095] Y 11 To Y 13 Can be C, Y 14 Can be N;

[0096] Y 12 To Y 14 Can be C, Y11 Can be N; or

[0097] Y 12 and Y 13 Can be C, Y 11 and Y 14 Both can be N.

[0098] In an exemplary embodiment, in Formula 1,

[0099] i)Y 11 and Y 14 Can all be N;

[0100] ii) Y 11 Can be C, M 11 With Y 11 The key between or B 11 With Y 11 The bond between can be a coordination bond;

[0101] iii) Y 14 Can be C, M 11 With Y 14 The key between or B 14 With Y 14 The bond between may be a coordination bond; or

[0102] iv) Y 11 and Y 14 Can be independently C, M 11 With Y 11 The key between or B 11 With Y 11 The bond between can be a coordination bond, and M 11 With Y 14 The key between or B 14 With Y 14 The bond between them can be a coordination bond.

[0103] In formula 1, B 11 To B 14 may each be independently selected from a single bond, *-O-*' and *-S-*'.

[0104] In an exemplary embodiment, in Formula 1, B 11 To B 14 Each of may be a single bond;

[0105] B 11 Can be selected from *-O-*' and *-S-*', B 12 To B 14 Can all be single bonds;

[0106] B 12Can be selected from *-O-*' and *-S-*', B 11 , B 13 and B 14 Can all be single bonds;

[0107] B 13 Can be selected from *-O-*' and *-S-*', B 11 , B 12 and B 14 can all be single bonds; or

[0108] B 14 Can be selected from *-O-*' and *-S-*', B 11 To B 13 They can all be single bonds.

[0109] In an exemplary embodiment, B 11 To B 14 Each of may be a single bond.

[0110] When B 11 When it is a single bond, M 11 and Y 11 Can be connected directly. 12 When it is a single bond, M 11 and Y 12 Can be connected directly. 13 When it is a single key, M 11 and Y 13 Can be connected directly. 14 When it is a single bond, M 11 and Y 14 Can connect directly.

[0111] In an exemplary embodiment, B 11 To B 14 Each of M can be a single key, 11 With Y 11 The key between 11 With Y 12 The key between 11 With Y 13 The key between M 11 With Y 14 Two bonds selected from among the bonds between may be coordinate bonds, and the other bond among them may be a covalent bond.

[0112] In an exemplary embodiment, B 11 To B 14 Each of M can be a single bond, 11 With Y 11 The key between M 11 With Y 14 The bond between M 11With Y 12 The key between M 11 With Y 13 The bond between them can be a covalent bond.

[0113] In formula 1, L 1 To L 3 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*'、*-C(R 16 )=*'、*=C(R 16 )-*'、*-C(R 16 )=C(R 17 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*'、*-N(R 16 )-*'、*-P(R 16 )-*'、*-Si(R 16 )(R 17 )-*' and *-Ge(R 16 )(R 17 )-*'.

[0114] In an exemplary embodiment, L 1 To L 3 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*'、*-B(R 16 )-*'、*-N(R 16 )-*'、*-Si(R 16 )(R 17 )-*' and *-P(R 16 )-*'.

[0115] In an exemplary embodiment, L 1 To L 3 may each be independently selected from a single bond, *-O-*' and *-S-*'.

[0116] a1 to a3 may be independently selected from 0, 1, 2 and 3, wherein at least two selected from a1 to a3 may be independently selected from 1, 2 and 3,

[0117] When a1 is 0, ring A 11 and Ring A 12 It can be disconnected. When a2 is 0, ring A 13 and Ring A 14 It can be disconnected. When a3 is 0, ring A 11 and Ring A14 It is not necessary to connect.

[0118] In an example embodiment, a1 and a2 may both be 1, and a3 may be 0;

[0119] a1 and a3 can both be 1, and a2 can be 0; or

[0120] a2 and a3 can both be 1, and a1 can be 0.

[0121] In an exemplary embodiment, L 1 and L 2 Both a1 and a2 can be single bonds, both a1 and a2 can be 1, and a3 can be 0.

[0122] In formula 1, X 1 and X 2 can be independently selected from O and S. In an exemplary embodiment, X 1 and X 2 Each of can be O, or X 1 and X 2 Each of can be S.

[0123] In formula 1, R 11 To R 17 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),

[0124] R 16 and R 11 , R 16 and R 12 , R 16 and R 13 and / or R 16 and R 14 Can be optionally linked to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group.

[0125] In the example embodiment, in Formula 1, when R from b11 is counted 11 At least one selected from and / or R from b14 14 At least one of the selected is substituted or unsubstituted C 1 -C 60 When the alkyl group is an alkyl group, the organometallic compound represented by Formula 1 may have stable optical and electrical properties.

[0126] In the exemplary embodiment, in Formula 1, when R from b11 is 11 At least one selected from and / or R from b14 14 At least one of the selected is substituted or unsubstituted C 6 -C 60 When the organometallic compound represented by Formula 1 is an aromatic group, the organic metal compound represented by Formula 1 can prevent the formation of an exciplex. In the exemplary embodiment, in Formula 1, when the number of R from b11 is 11 Select at least one of b and R from b14 numbers14 At least one of the selected is substituted or unsubstituted C 6 -C 60 In the case of an aromatic group, the π-π interaction caused by multiple aromatic groups can provide an additional stabilizing effect.

[0127] In an exemplary embodiment, R 11 To R 17 Can be independently selected from:

[0128] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0129] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0130] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzosilolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzosilyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzosilyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, and indolocarbazolyl;

[0131] All are substituted with deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazole yl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothioyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothioyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothioyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, indolocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32) is at least one selected from cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentacene, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothirolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, oxazolyl, tetrazolyl, thiadiazolyl, oxadiazolyl, triazine, carbazolyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthobenzothiophenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothiophenyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzothiophenyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl, and indolocarbazolyl; and

[0132] -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ).

[0133] In an exemplary embodiment, R 11 To R 17 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1-C 20 Alkyl and C 1 -C 20 Alkoxy;

[0134] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy; and

[0135] A group represented by one selected from Formula 5-1 to Formula 5-25 and Formula 6-1 to Formula 6-55:

[0136]

[0137]

[0138]

[0139]

[0140] In Formulas 5-1 to 5-25 and 6-1 to 6-55,

[0141] Y 31 Can be O, S, C (Z 34 )(Z 35 )、N(Z 34 ) or Si(Z 34 )(Z 35 ),

[0142] Z 31 To Z 35 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkenyl, C 1 -C 20 Alkynyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl and triazinyl,

[0143] e2 can be 1 or 2,

[0144] e3 can be an integer from 1 to 3,

[0145] e4 can be an integer from 1 to 4,

[0146] e5 can be an integer from 1 to 5,

[0147] e6 can be an integer from 1 to 6,

[0148] e7 can be an integer from 1 to 7,

[0149] e9 can be an integer from 1 to 9, and

[0150] *Indicates the binding site with the adjacent atom.

[0151] In an exemplary embodiment, R 11 To R 17 Can be independently selected from:

[0152] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0153] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0154] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl, and triazinyl; and

[0155] The phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, phenanthryl groups, anthracenyl groups, pyridyl groups, pyrimidinyl groups, carbazolyl groups and triazine groups are all substituted with at least one group selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl group, terphenyl group, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, phenanthryl groups, anthracenyl groups, pyridyl groups, pyrimidinyl groups, carbazolyl groups and triazine groups.

[0156] In Formula 1, b11 to b15 may each independently be an integer of 1 to 10.

[0157] b11 represents R 11 The number of, wherein, when b11 is two or greater, two or more R 11 May be the same as or different from each other.

[0158] b12 represents R 12 The number of, wherein, when b12 is two or more, two or more R 12 May be the same as or different from each other.

[0159] b13 represents R 13The number of, wherein, when b13 is two or more, two or more R 13 May be the same as or different from each other.

[0160] b14 represents R 14 The number of, wherein, when b14 is two or more, two or more R 14 May be the same as or different from each other.

[0161] b15 represents R 15 The number of, where, when b15 is two or more, two or more R 15 May be the same as or different from each other.

[0162] In an exemplary embodiment, the formula (1) is The part represented can be expressed by formula 1-1:

[0163] <Formula 1-1>

[0164]

[0165] In formula 1-1,

[0166] X 41 Can be N or C (R 41 ), X 42 Can be N or C (R 42 ), X 43 Can be N or C (R 43 ), X 44 Can be N or C (R 44 ), X 45 Can be N or C (R 45 ), X 46 Can be N or C (R 46 ), X 47 Can be N or C (R 47 ),

[0167] R 41 and R 42 can be independently combined with R in formula 1 12 Same as described,

[0168] R 43 To R 45 can be independently combined with R in formula 1 15 Same as described,

[0169] R 46 and R 47 can be independently combined with R in formula 1 13 Same as described,

[0170] X 1 and X2 may be independently the same as described in Formula 1,

[0171] * indicates the same as B in formula 1 12 and B 13 The binding position of

[0172] *' represents the same as (L 1 ) a1 The binding site of

[0173] *" indicates the same as (L 2 ) a2 The combination position.

[0174] In an exemplary embodiment, the formula (1) is The part represented can be expressed by formula 1-2:

[0175] <Formula 1-2>

[0176]

[0177] In formula 1-2,

[0178] R 41 and R 42 can be independently combined with R in formula 1 12 Same as described,

[0179] R 43 To R 45 can be independently combined with R in formula 1 15 Same as described,

[0180] R 46 and R 47 can be independently combined with R in formula 1 13 Same as described,

[0181] X 1 and X 2 may be independently the same as described in Formula 1,

[0182] * indicates the same as B in formula 1 12 and B 13 The binding position of

[0183] *' represents the same as (L 1 ) a1 The binding site of

[0184] *" indicates the same as (L 2 ) a2 The combination position.

[0185] In example embodiments, in Formula 1-1 and Formula 1-2, R41 To R 47 Can be independently selected from:

[0186] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0187] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0188] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl, and triazinyl; and

[0189] The phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, phenanthryl groups, anthracenyl groups, pyridyl groups, pyrimidinyl groups, carbazolyl groups and triazine groups are all substituted with at least one group selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl group, terphenyl group, naphthyl groups, fluorenyl groups, spirobifluorenyl groups, phenanthryl groups, anthracenyl groups, pyridyl groups, pyrimidinyl groups, carbazolyl groups and triazine groups.

[0190] In example embodiments, in Formula 1-1 and Formula 1-2, R 41 To R 47 They may be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and phenyl.

[0191] In example embodiments, in Formula 1-1 and Formula 1-2, R 41 To R 47 Each of may be hydrogen.

[0192] Substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

[0193] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0194] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 (Q11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0195] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;

[0196] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0197] -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 ),

[0198] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and

[0199] * and *' both indicate the binding sites with adjacent atoms.

[0200] In example embodiments, the organometallic compound represented by Formula 1 may be selected from Compound 1 to Compound 25:

[0201]

[0202]

[0203]

[0204] The organic metal compound represented by Formula 1 may include The part represented by (hereinafter, referred to as "part A") is shown in FIG. 1 . Part A may include a boron atom and X 1 Atom and X 2 The atom (oxygen atom or sulfur atom) destroys the conjugated structure of the aromatic ring.

[0205] Without being bound by theory, it is believed that in such a structure, the emission wavelength is shifted to a short wavelength, so that the organometallic compound represented by Formula 1 can emit blue light with high color purity.

[0206] In addition, it is believed that since the organometallic compound including the moiety A has a relatively small ΔE compared to a compound including a linker other than a linker including a condensed ring structure such as the moiety A, ST , so the lifetime of triplet excitons can be shortened. Therefore, when the organometallic compound is applied to an organic light-emitting device, energy transfer can be promoted and the luminous efficiency can be improved.

[0207] In addition, it is believed that when ring A in the organometallic compound represented by Formula 1 11 and Ring A14 When at least one of the selected rings A includes a carbene, the binding energy between carbon and the metal center is stronger than the binding energy between carbon and nitrogen. Therefore, the organometallic compound has a more stable structure optically and / or electrically, thereby realizing a light-emitting device with a long life. On the other hand, a carbene can be introduced into the ring A. 11 and Ring A 14 In at least one of the above, an asymmetric molecular structure is induced in the whole molecule. When the organometallic compound has an asymmetric molecular structure, the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound is relatively increased. Therefore, the emission wavelength is shifted to a short wavelength, thereby emitting blue light with high color purity.

[0208] In addition, when the organometallic compound represented by Formula 1 includes the portion A, the organometallic compound may have a rigid structure. Therefore, an organic light emitting device including the organometallic compound may have high durability and a long lifespan.

[0209] The synthesis method for the organometallic compound represented by Formula 1 will be apparent to those skilled in the art by referring to the following examples.

[0210] The organic metal compound of Formula 1 may be used between a pair of electrodes of an organic light emitting device. In example embodiments, the organic metal compound may be included in an emission layer. The organic metal compound may serve as a dopant in the emission layer.

[0211] In example embodiments, the organometallic compound of Formula 1 may be used as a material for a capping layer that is located outside a pair of electrodes of an organic light emitting device.

[0212] In example embodiments, an organic light emitting device includes a first electrode, a second electrode facing the first electrode, an organic layer between the first electrode and the second electrode and including an emission layer, and at least one organic metal compound represented by Formula 1.

[0213] In example embodiments, an organic layer of an organic light emitting device may include an organic metal compound represented by Formula 1.

[0214] As used herein, the expression “(organic layer) includes at least one of the organic metal compounds” may include the case where “(organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0215] In example embodiments, the organic layer may include only Compound 1 as an organic metal compound. In this regard, Compound 1 may be present in the emission layer of the organic light-emitting device. In example embodiments, the organic layer may include Compound 1 and Compound 2 as organic metal compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., Compound 1 and Compound 2 may both be present in the emission layer), or in different layers (e.g., Compound 1 may be present in the emission layer and Compound 2 may be present in the electron transport layer).

[0216] In example embodiments, an emission layer of an organic light emitting device may include at least one organic metal compound.

[0217] In example embodiments, the emission layer of the organic light-emitting device may include at least one organic metal compound, and the emission layer may further include a host. The amount of the host included in the emission layer may be greater than the amount of the organic metal compound included in the emission layer. In example embodiments, the amount of the organic metal compound included in the emission layer may be about 0.01 parts by weight to about 30 parts by weight based on 100 parts by weight of the emission layer.

[0218] In an example embodiment, the body may include two different bodies.

[0219] The weight ratio of the two different bodies can be about 90:10 to about 10:90. In example embodiments, the weight ratio of the two different bodies can be about 80:20, about 70:30, about 60:40, about 50:50, about 40:60, about 30:70, or about 20:80. For example, the weight ratio of the two different bodies can be about 50:50.

[0220] In example embodiments, the host may include a first host and a second host. The first host may include a carbazole-containing host or a silyl-containing host, and the second host may include a phosphine oxide-containing host.

[0221] In example embodiments, the emission layer may include an organic metal compound, and the emission layer may emit blue light. In example embodiments, the emission layer may emit blue light having a maximum emission wavelength of about 430 nm to about 490 nm (e.g., about 450 nm to about 485 nm or about 452 nm to about 470 nm).

[0222] In an exemplary embodiment, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0223] In example embodiments, the electron transport region may include a phosphine oxide-containing compound or a silyl group-containing compound. In example embodiments, the electron transport region may include a hole blocking layer directly contacting the emission layer and including the phosphine oxide-containing compound or the silyl group-containing compound.

[0224] The term "organic layer" as used herein refers to a single layer and / or a plurality of layers disposed between a first electrode and a second electrode of an organic light emitting device. The material included in the "organic layer" is not limited to an organic material.

[0225] [ Figure 1 Description]

[0226] Figure 1 1 is a schematic diagram of an organic light emitting device 10 according to an example embodiment. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0227] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 and a method of manufacturing the organic light emitting device 10 according to example embodiments will be described.

[0228] [First electrode 110]

[0229] exist Figure 1 In the embodiment, a substrate may be additionally disposed under the first electrode 110 or over the second electrode 190. The substrate may be a glass substrate or a plastic substrate, both of which have excellent mechanical strength, thermal stability, transparency, surface flatness, easy handling, and waterproofness.

[0230] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0231] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and combinations thereof. When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, for example, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or combinations thereof may be used as a material for forming the first electrode 110.

[0232] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. In example embodiments, the first electrode 110 may have a triple-layer structure, for example, ITO / Ag / ITO.

[0233] [Organic layer 150]

[0234] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.

[0235] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .

[0236] [Hole Transport Region in Organic Layer 150]

[0237] The hole transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0238] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.

[0239] In example embodiments, the hole transport region may have a single-layer structure including a single layer containing a plurality of different materials, or a multilayer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110, for example, in the order stated.

[0240] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0241]

[0242] <Formula 201>

[0243]

[0244] <Formula 202>

[0245]

[0246] In equation 201 and equation 202,

[0247] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0248] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0249] xa1 to xa4 may each independently be an integer from 0 to 3,

[0250] xa5 can be an integer from 1 to 10,

[0251] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0252] In an exemplary embodiment, in equation 202, R 201 and R 202 The connection may be via a single bond, dimethyl-methylene or diphenyl-methylene, R 203 and R 204 The attachment may be via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0253] In an example embodiment, in equation 201 and equation 202,

[0254] L 201 To L 205 Can be independently selected from:

[0255] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and

[0256] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one selected from phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalene, indacenylene, acenaphthenylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, tetraphenylene, perylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, rubidinylene, camphenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridylene, and

[0257] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1-C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0258] In example embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

[0259] In example embodiments, xa5 may be 1, 2, 3, or 4.

[0260] In an exemplary embodiment, R 201 To R 204 and Q 201 Can be independently selected from:

[0261] Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0262] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32) is at least one selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl, and

[0263] Q 31 To Q 33 Same as described above.

[0264] In an exemplary embodiment, in equation 201, from R 201 To R 203 At least one of the selected ones can be independently selected from:

[0265] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

[0266] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Phenyl group of the alkyl group, phenyl group substituted with -F, naphthyl group, fluorenyl group, spirobifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; at least one selected from fluorenyl group, spirobifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group.

[0267] In an exemplary embodiment, in Formula 202, i) R 201 and R 202 can be connected via a single bond, and / or ii) R 203 and R 204 Can connect via one-touch.

[0268] In an exemplary embodiment, in equation 202, from R 201 To R 204 At least one of the selected ones may be selected from:

[0269] carbazolyl; and

[0270] Substitutions include deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 The alkyl group is a phenyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a carbazolyl group selected from at least one group.

[0271] The compound represented by Formula 201 can be represented by Formula 201A:

[0272] <Formula 201A>

[0273]

[0274] In example embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1):

[0275]

[0276] In example embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1:

[0277]

[0278] In example embodiments, the compound represented by Formula 202 may be represented by Formula 202A:

[0279] <Formula 202A>

[0280]

[0281] In example embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

[0282] <Formula 202A-1>

[0283]

[0284] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,

[0285] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,

[0286] R 211 and R 212 can be independently combined with R 203 are defined identically, and

[0287] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, substituted with C 1 -C 10 Alkyl phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, peryl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, camphenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl.

[0288] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39:

[0289]

[0290]

[0291]

[0292] The thickness of the hole transport region may be about to about For example, about to about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about For example, about to about The thickness of the hole transport layer can be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.

[0293] The emission auxiliary layer can improve light emitting efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer can include materials as described above.

[0294] [p dopant]

[0295] In addition to these materials, the hole transport region may also include a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0296] The charge generating material may be, for example, a p-dopant.

[0297] In example embodiments, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of −3.5 eV or less.

[0298] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds.

[0299] In example embodiments, the p-dopant may include at least one selected from the following compounds:

[0300] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0301] Metal oxides, such as tungsten oxide and / or molybdenum oxide;

[0302] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0303] The compound represented by formula 221:

[0304]

[0305] <Formula 221>

[0306]

[0307] In formula 221,

[0308] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 To R 223 At least one selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted with -Cl 1 -C 20 Alkyl, C substituted with -Br 1 -C 20 Alkyl and C substituted with -I 1 -C 20 At least one substituent selected from the group consisting of:

[0309] [Emission Layer in Organic Layer 150]

[0310] When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to the sub-pixel. In an example embodiment, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In an example embodiment, the emission layer may include two or more materials selected from a red light emitting material, a green light emitting material, and a blue light emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0311] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.

[0312] In the emission layer, the amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0313] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within this range, excellent light emitting characteristics may be obtained without significantly increasing driving voltage.

[0314] [Subject in the emission layer]

[0315] In an example embodiment, the host may include a compound represented by Formula 301:

[0316] <Formula 301>

[0317] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21。

[0318] In formula 301,

[0319] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0320] xb11 can be 1, 2 or 3,

[0321] L 301 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0322] xb1 can be an integer from 0 to 5.

[0323] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 301 )(Q 302 ),

[0324] xb21 can be an integer from 1 to 5, and

[0325] Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0326] In an exemplary embodiment, Ar in Formula 301 301 Can be selected from:

[0327] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, phenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and

[0328] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ) is at least one of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, and

[0329] Q 31 To Q 33 can be independently selected from, for example, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0330] When xb11 in Formula 301 is two or more, two or more Ar 301 Can connect via one-touch.

[0331] In example embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:

[0332] <Formula 301-1>

[0333]

[0334] <Formula 301-2>

[0335]

[0336] In Formula 301-1 and Formula 301-2,

[0337] A 301 To A 304can be independently selected from benzene, naphthalene, phenanthrene, fluoranthene, benzo[9,10]phenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthiophene, benzonaphthothiophene and dinaphthothiophene,

[0338] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0339] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ),

[0340] xb22 and xb23 can each independently be 0, 1 or 2,

[0341] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,

[0342] L 302 To L 304 can be independently combined with L 301 The same definition,

[0343] xb2 to xb4 may each independently be the same as defined in conjunction with xb1, and

[0344] R 302 To R 304 can be independently combined with R301 The definition is the same.

[0345] In an example embodiment, in equation 301, equation 301-1, and equation 301-2, L 301 To L 304 Can be independently selected from:

[0346] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and

[0347] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -Si(Q 31 )(Q 32 )(Q33 )、-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 ) is at least one of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene, and

[0348] Q 31 To Q 33 Same as described above.

[0349] In an exemplary embodiment, in equation 301, equation 301-1, and equation 301-2, R 301 To R 304 Can be independently selected from:

[0350] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0351] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, and

[0352] Q 31 To Q 33 Same as described above.

[0353] In example embodiments, the host may include an alkaline earth metal complex. In example embodiments, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.

[0354] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-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-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55:

[0355]

[0356]

[0357]

[0358] [Phosphorescent Dopant in Emission Layer Included in Organic Layer 150]

[0359] The phosphorescent dopant may include an organic metal compound represented by Formula 1.

[0360] The phosphorescent dopant may include an organometallic complex represented by Formula 401:

[0361] <Formula 401>

[0362] M(L 401 ) xc1 (L 402 ) xc2

[0363] <Formula 402>

[0364]

[0365] In equations 401 and 402,

[0366] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),

[0367] L 401 can be selected from the ligand represented by formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is two or more, two or more L 401 can be the same or different from each other,

[0368] L 402 may be an organic ligand, and xc2 may be an integer from 0 to 4, wherein when xc2 is two or more, two or more L 402 can be the same or different from each other,

[0369] X 401 To X 404 may each independently be nitrogen or carbon,

[0370] X 401 and X 403 Can be connected via single or double bonds, X 402 and X 404 Can be connected via single or double bonds,

[0371] A 401 and A 402 can be independently selected from C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0372] X 405 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=*', where Q 411 and Q 412 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,

[0373] X 406 Can be a single bond, O or S,

[0374] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C1 -C 20 Heteroaryl,

[0375] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0376] The * and *' in formula 402 both represent the binding site with M in formula 401.

[0377] In an exemplary embodiment, A in equation 402 401 and A 402 They can all be independently selected from benzene, naphthalene, fluorene, spirobifluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran and dibenzothiophene.

[0378] In an exemplary embodiment, in equation 402, i) X 401 Can be nitrogen, X 402 It can be carbon, or ii) X 401 and X 402 They may both be nitrogen.

[0379] In an exemplary embodiment, R in equation 402 401 and R 402 Can be independently selected from:

[0380] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0381] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0382] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;

[0383] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 at least one selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0384] -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 ) and -P(=O)(Q 401 )(Q 402 ),and

[0385] Q 401 To Q 403 can be independently selected from, for example, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl and naphthyl.

[0386] In an exemplary embodiment, when xc1 in equation 401 is two or greater, two or more L 401 Two A's 401 It can be connected via X 407 Connect, or two or more L 401 Two A's 402 It can be connected via X 408 Connection (see Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408 Each of them can be independently, for example, a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413)-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl).

[0387] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand. In an exemplary embodiment, L 402 It may be selected from halogen, diketone (eg, acetylacetone), carboxylic acid (eg, picolinic acid), -C(=O), isonitrile, -CN and phosphorus (eg, phosphine or phosphite).

[0388] In example embodiments, the phosphorescent dopant may be selected from, for example, Compound PD1 to Compound PD25:

[0389]

[0390]

[0391] [Fluorescent dopants in the emission layer]

[0392] The fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0393] The fluorescent dopant may include a compound represented by Formula 501:

[0394] <Formula 501>

[0395]

[0396] In formula 501,

[0397] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0398] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0399] xd1 to xd3 may each independently be an integer from 0 to 3,

[0400] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

[0401] xd4 can be an integer from 1 to 6.

[0402] In an exemplary embodiment, Ar in Formula 501 501 Can be selected from:

[0403] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and

[0404] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C20 Alkyl, C 1 -C 20 at least one selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The following examples include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33,

[0405] In an exemplary embodiment, L in equation 501 501 To L 503 Can be independently selected from:

[0406] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...

[0407] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene group, a naphthylene group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, an anthracene group, an fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a fluoranthrenyl group, a benzo[9,10]phenanthrenyl group, a py ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.

[0408] In an exemplary embodiment, R in equation 501 501 and R 502 Can be independently selected from:

[0409] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and

[0410] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl, and

[0411] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0412] In an example embodiment, xd4 in equation 501 may be 2.

[0413] In example embodiments, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:

[0414]

[0415]

[0416] In example embodiments, the fluorescent dopant may be selected from the following compounds.

[0417]

[0418] [Electron Transport Region in Organic Layer 150]

[0419] The electron transport region may have: i) a single layer structure including a single layer including a single material; ii) a single layer structure including a single layer including a plurality of different materials; or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0420] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer.

[0421] In example embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the emission layer in the order stated.

[0422] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.

[0423] The term "π-electron-poor nitrogen-containing ring" refers to a C- 1 -C 60 Heterocyclic group.

[0424] In example embodiments, the “π-electron-poor nitrogen-containing ring” may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' moiety are condensed with each other; or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' moiety is condensed with at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.

[0425] Examples of π-electron-poor nitrogen-containing rings include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0426] In example embodiments, the electron transport region may include a compound represented by Formula 601:

[0427] <Formula 601>

[0428] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0429] In formula 601,

[0430] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0431] xe11 can be 1, 2 or 3,

[0432] L 601 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0433] xe1 can be an integer from 0 to 5,

[0434] R 601 Can be selected from substituted or unsubstituted C 3 -C10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0435] Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0436] xe21 can be an integer from 1 to 5.

[0437] In the example embodiment, xe11 number of Ar 601 At least one and / or xe21 number of R 601 At least one of the may include a π-electron-poor nitrogen-containing ring.

[0438] In an exemplary embodiment, Ar in Formula 601 601 Can be selected from:

[0439] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...

[0440] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, naphthyl, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl, and

[0441] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0442] When xe11 in Formula 601 is two or greater, two or more Ar 601 Can connect via one-touch.

[0443] In an exemplary embodiment, Ar in Formula 601 601 It may be anthracene.

[0444] In example embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

[0445] <Formula 601-1>

[0446]

[0447] In formula 601-1,

[0448] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and from X 614 To X 616 At least one of the selected ones may be N,

[0449] L 611 To L 613 can be independently combined with L 601 Same as described,

[0450] xe611 to xe613 can each independently be the same as described in conjunction with xe1,

[0451] R 611 To R 613 can be independently combined with R 601 Same as described, and

[0452] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0453] In an exemplary embodiment, L in equation 601 601 and L in formula 601-1 611 To L 613 For example, they can be independently selected from:

[0454] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and

[0455] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazine at least one selected from the group consisting of phenylene, naphthylene, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene.

[0456] In example embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 may each independently be 0, 1, or 2.

[0457] In an exemplary embodiment, R in equation 601 601 and R in formula 601-1 611 To R 613 Can be independently selected from:

[0458] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;

[0459] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0460] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and

[0461] Q 601 and Q 602 Can be the same as described above.

[0462] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36:

[0463]

[0464]

[0465]

[0466] In example embodiments, the electron transport region may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one compound selected from the group consisting of BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:

[0467]

[0468] The thickness of the buffer layer, hole blocking layer or electron control layer can each independently be about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the electron transport region may have excellent hole blocking characteristics or electron control characteristics without significantly increasing driving voltage.

[0469] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within the above range, the electron transport layer may have satisfactory electron transport characteristics without significantly increasing driving voltage.

[0470] In addition to the materials described above, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.

[0471] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ion, Na ion, K ion, Rb ion and Cs ion, and the alkaline earth metal complex may include a metal ion selected from Be ion, Mg ion, Ca ion, Sr ion and Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene.

[0472] In an exemplary embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium 8-hydroxyquinoline, LiQ) or compound ET-D2.

[0473]

[0474] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0475] The electron injection layer may have: i) a single-layer structure including a single layer containing a single material; ii) a single-layer structure including a single layer containing multiple different materials; or iii) a multi-layer structure having multiple layers including multiple different materials.

[0476] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.

[0477] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In an exemplary embodiment, the alkali metal may be Li, Na, or Cs. In an exemplary embodiment, the alkali metal may be Li or Cs.

[0478] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0479] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0480] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0481] The alkali metal compound may be selected from alkali metal oxides such as Li 2 O, Cs 2 O, or K 2 O and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In an exemplary embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI.

[0482] The alkaline earth metal compound may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1), or Ba x Ca 1-xAlkaline earth metal oxides of O(0 < x < 1). In an exemplary embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO.

[0483] The rare earth metal compound may be selected from YbF 3 , ScF 3 , Sc 2 O 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 . In an exemplary embodiment, the rare earth metal compound may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 and TbI 3 .

[0484] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligands coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene.

[0485] The electron injection layer may be composed of or include the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof as described above. In an exemplary embodiment, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or a combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0486] The thickness of the electron injection layer may be about to about For example, about to about When the thickness of the electron injection layer is within the above range, the electron injection layer may have satisfactory electron injection characteristics without significantly increasing driving voltage.

[0487] [Second electrode 190]

[0488] The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be a material having a low work function, such a material may be a metal, an alloy, a conductive compound, or a combination thereof.

[0489] The second electrode 190 may 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), ITO, and IZO. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0490] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0491] [ Figures 2 to 4 Description]

[0492] Figure 2 The organic light emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 which are sequentially stacked in the order stated, Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220 sequentially stacked in the order of this statement, Figure 4 The organic light emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 which are sequentially stacked in the stated order.

[0493] about Figures 2 to 4 , can be combined by reference Figure 1 The description is given to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .

[0494] In the organic layer 150 of each of the organic light-emitting devices 20 and the organic light-emitting devices 40, light generated in the emission layer can pass through the first electrode 110 (which is a semi-transmissive electrode or a transmissive electrode) and the first cover layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and the organic light-emitting devices 40, light generated in the emission layer can pass through the second electrode 190 (which is a semi-transmissive electrode or a transmissive electrode) and the second cover layer 220 toward the outside.

[0495] The first capping layer 210 and the second capping layer 220 may improve external light emitting efficiency according to the principle of constructive interference.

[0496] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

[0497] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may be selectively substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In example embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may independently include an amine compound.

[0498] In example embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0499] In example embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5.

[0500]

[0501] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region may be formed in a set or predetermined region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.

[0502] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and approx. / second to about The vacuum deposition was performed at a deposition rate of 2000 Å / s.

[0503] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to about 200°C, depending on the material to be included in the layer to be formed and the structure of the layer to be formed.

[0504] [General Definition of Substituents]

[0505] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, non-limiting examples of which include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to C 1 -C 60 An alkyl group is a divalent group having the same structure.

[0506] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by substituting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and non-limiting examples thereof include vinyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to C 2 -C 60 Alkenyl groups have divalent groups of the same structure.

[0507] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by replacing at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, non-limiting examples of which include ethynyl and propynyl. 2 -C 60 "Alkynylidene" refers to a C 2 -C 60 Alkynyl groups are divalent groups with the same structure.

[0508] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101 C 1 -C 60The monovalent group represented by an alkyl group is a methoxy group, an ethoxy group, and an isopropoxy group.

[0509] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "C 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group of the same structure.

[0510] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom and 1 to 10 carbon atoms, non-limiting examples of which include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.

[0511] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, non-limiting examples of which include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has a divalent group of the same structure.

[0512] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a C 1 -C 10The heterocycloalkenyl group has a divalent group of the same structure.

[0513] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0514] As used herein, the term "C 1 -C 60 The term "heteroaryl" as used herein refers to a monovalent group having a heterocyclic aromatic system having, in addition to 1 to 60 carbon atoms, at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having, in addition to 1 to 60 carbon atoms, at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0515] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C 6 -C 60 Aryl), the term "C 6 -C 60 "Arylthio" means -SA 103 (Among them, A 103 C 6 -C 60 aryl).

[0516] As used herein, the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings condensed with each other, only carbon atoms (e.g., 8 to 60 carbon atoms) as ring atoms, and containing at least one non-aromatic ring in its entire molecular structure. A non-limiting example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0517] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein refers to a monovalent group having two or more rings condensed with each other, at least one heteroatom selected from N, O, Si, P and S other than carbon atoms (e.g., 1 to 60 carbon atoms) as a ring-forming atom, and containing at least one non-aromatic ring in its entire molecular structure. A non-limiting example of a monovalent non-aromatic condensed heteropolycyclic group is 9,10-dihydroacridinyl. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0518] As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group may be a ring such as benzene, a monovalent group such as phenyl, or a divalent group such as phenylene. 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0519] As used herein, the term "C 1 -C 60 The term "heterocyclic group" refers to a group consisting of at least one heteroatom selected from N, O, Si, P and S other than carbon (the number of carbon atoms may be in the range of 1 to 60) as a ring-forming atom. 5 -C 60 The carbocyclic group has a group of the same structure.

[0520] In this specification, substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C20 Alkylene, substituted C 2 -C 20 Alkenylene, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

[0521] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0522] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0523] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;

[0524] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0525] -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 ),and

[0526] Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.

[0527] As used herein, the term "Ph" may refer to a phenyl group; as used herein, the term "Me" may refer to a methyl group; as used herein, the term "Et" may refer to an ethyl group; as used herein, the term "ter-Bu" or "Bu t " may refer to tert-butyl; the term "OMe" as used herein may refer to methoxy.

[0528] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". In other words, a "biphenyl group" is a group having C 6 -C 60A phenyl group substituted with an aryl group as a substituent.

[0529] As used herein, the term "terphenyl" refers to a "phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" is a group having a C 6 -C 60 Aryl C 6 -C 60 Phenyl with aryl as substituent.

[0530] Unless otherwise defined, *, *' and *" as used herein all refer to the binding sites to adjacent atoms in the corresponding formula.

[0531] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it will be understood that the examples and comparative examples are not to be construed as limiting the scope of the embodiments, and the comparative examples are not to be construed as being outside the scope of the embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0532] The expression "B is used instead of A" used in describing the synthesis examples means that the same molar equivalent of B is used instead of the same molar equivalent of A.

[0533] [Synthesis example]

[0534] Synthesis Example 1: Synthesis of Compound 1

[0535]

[0536] (1) Synthesis of intermediate [1-A]

[0537] 20.0g (114.28mmol) of 1-bromo-4-fluorobenzene, 6.29g (57.14mmol) of resorcinol, 15.4g (137.24mmol) of potassium tert-butoxide and 1.00g of copper iodide were suspended in 200mL of dimethylformamide solvent, heated to a temperature of 140°C and stirred for 48 hours. The organic layer was extracted from the reaction mixture using dichloromethane and distilled water. The extracted organic layer was washed 3 times with distilled water, dried, filtered and concentrated under reduced pressure by using anhydrous magnesium sulfate. The concentrate thus obtained was purified by column chromatography to obtain 5.96g of intermediate [1-A] (yield 35%).

[0538] (2) Synthesis of intermediate [1-B]

[0539] 5.80g (19.4mmol) of the intermediate [1-A] synthesized as described above was dissolved in 40mL of o-xylene, added dropwise to a hexane solution of n-butyl lithium (n-BuLi) (1.05eq) at a temperature of -78°C, heated to a temperature of 70°C, and then stirred for 4 hours. Then, the reaction mixture was cooled to a temperature of -40°C, and boron tribromide (1.2eq) was added dropwise thereto, stirred at room temperature for 1 hour, and then stirred at a temperature of 40°C for 1 hour. The solvent was removed therefrom by concentrating under reduced pressure. N, N-diisopropylethylamine (2.0eq) was added thereto, and stirred at a temperature of 120°C for 5 hours. The reaction mixture was filtered and washed with methanol to obtain 4.76g of the intermediate [1-B] (yield 42%).

[0540] (3) Synthesis of intermediate [1-C]

[0541] 4.50 g (15.09 mmol) of the intermediate [1-B] synthesized as described above, 2.06 g (30.18 mmol) of imidazole and 4.17 g (30.18 mmol) of potassium carbonate were dissolved in dimethylformamide and stirred at a temperature of 150° C. for 12 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The concentrate thus obtained was purified by column chromatography (developing solvent was ethyl acetate: n-hexane = 5:1 to 2:1) to obtain 4.86 g of the intermediate [1-C] (yield 80%).

[0542] (4) Synthesis of intermediate [1-D]

[0543] Intermediate [1-C] (1.0 eq) was dissolved in acetone, and iodomethane (MeI) (2.2 eq) was added thereto and stirred at room temperature for 3 days. The reaction mixture was concentrated under reduced pressure and subjected to column chromatography to obtain Intermediate [1-D] (yield 91%).

[0544] (5) Synthesis of intermediate [1-E]

[0545] Intermediate [1-D] (1.0 eq) was dissolved in a solvent in which methanol and water were mixed at a ratio of 4:1, and ammonium hexafluorophosphate (2.0 eq) was added thereto and stirred at room temperature for 1 day. The solid thus obtained was filtered and washed with diethyl ether to obtain Intermediate [1-E] (yield 95%).

[0546] (6) Synthesis of Compound 1

[0547] The intermediate [1-E] (1.0 eq) synthesized as described above, potassium tetrachloroplatinate (K 2 PtCl 4) (1.1 eq) and tetrabutylammonium bromide (0.1 eq) were dissolved in acetic acid (AcOH) (0.1 M), and stirred at a temperature of 120° C. for 72 hours. The reaction mixture was cooled to room temperature, and an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried and concentrated by using anhydrous magnesium sulfate, and column chromatography was performed thereon to obtain compound 1 (yield 22%).

[0548] Synthesis Example 2: Synthesis of Compound 2

[0549] Compound 2 was obtained in the same manner as in Synthesis Example 1, except that pyrazole was used instead of imidazole in the synthesis intermediate [1-C].

[0550] Synthesis Example 3: Synthesis of Compound 4

[0551] Compound 4 was obtained in the same manner as in Synthesis Example 1, except that the reaction was performed by using diphenyliodonium tetrafluoroborate instead of methyl iodide in Synthesis Intermediate [1-D].

[0552] Synthesis Example 4: Synthesis of Compound 5

[0553] Compound 5 was obtained in the same manner as in Synthesis Example 1, except that the intermediate was obtained by a two-step reaction in which 1 eq of 3,5-dimethylpyrazole was used instead of 2 eq of imidazole in the synthetic intermediate [1-C], and then 1 eq of imidazole was used.

[0554] Synthesis Example 5: Synthesis of Compound 7

[0555]

[0556] (1) Synthesis of intermediate [7-A]

[0557] Intermediate [7-A] was obtained in the same manner as in the synthesis of Intermediate [1-C], except that a metal catalyst reaction using pyridine instead of imidazole was performed in the synthesis of Intermediate [1-C].

[0558] (2) Synthesis of Compound 7

[0559] Compound 7 was obtained in the same manner as in the synthesis of Compound 1, except that Intermediate [7-A] was used instead of Intermediate [1-E] in the synthesis of Compound 1.

[0560] Synthesis Example 6: Synthesis of Compound 8

[0561] Compound 8 was obtained in the same manner as in Synthesis Example 1, except that a metal catalyst reaction was performed using 1 eq of pyridine instead of 2 eq of imidazole in Synthesis Intermediate [1-C], and then 1 eq of imidazole was used.

[0562] Synthesis Example 7: Synthesis of Compound 10

[0563] Compound 10 was obtained in the same manner as in Synthesis Example 6, except that triazole was used instead of imidazole in the synthesis intermediate [1-C].

[0564] Synthesis Example 8: Synthesis of Compound 11

[0565] Compound 11 was obtained in the same manner as in Synthesis Example 6, except that 4-tert-butylpyridine was used instead of pyridine.

[0566] Synthesis Example 9: Synthesis of Compound 19

[0567] Compound 19 was obtained in the same manner as in Synthesis Example 1, except that benzimidazole was used instead of imidazole in the synthesis intermediate [1-C].

[0568] Synthesis Example 10: Synthesis of Compound 21

[0569]

[0570] (1) Synthesis of intermediate [21-A]

[0571] 10.0 g (57.14 mmol) of 1-bromo-4-fluorobenzene, 6.04 g (62.85 mmol) of 3,5-dimethylpyrazole and 8.68 g (62.85 mmol) of potassium carbonate were dissolved in dimethylformamide and stirred at a temperature of 150° C. for 12 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The concentrate thus obtained was purified by column chromatography (developing solvent was ethyl acetate: n-hexane = 10: 1 to 5: 1) to obtain 11.50 g of intermediate [21-A] (yield 80%).

[0572] (2) Synthesis of intermediate [21-B]

[0573] 11.50g (45.80mmol) of intermediate [21-A] synthesized as described above, 2.52g (22.90mmol) of resorcinol, 10.27g (91.60mmol) of potassium tert-butoxide and 0.87g of copper iodide were suspended in 200mL of dimethylformamide solvent, heated to a temperature of 140°C, and then stirred for 48 hours. The organic layer was extracted from the reaction mixture using dichloromethane and distilled water. The extracted organic layer was washed 3 times with distilled water, dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate thus obtained was purified by column chromatography to obtain 11.14g of intermediate [21-B] (yield 54%).

[0574] (3) Synthesis of intermediate [21-C]

[0575] 11.14g (24.73mmol) of the intermediate [21-B] synthesized as described above was dissolved in 40mL of o-xylene, added dropwise to a hexane solution of n-butyl lithium (1.05eq) at a temperature of -78°C, heated to a temperature of 70°C, and then stirred for 4 hours. Then, the reaction mixture was cooled to a temperature of -40°C, and boron tribromide (1.2eq) was added dropwise thereto, stirred at room temperature for 1 hour, and then stirred at a temperature of 40°C for 1 hour. The solvent was removed therefrom by concentrating under reduced pressure. N,N-diisopropylethylamine (2.0eq) was added thereto, and stirred at a temperature of 120°C for 5 hours. The reaction mixture was filtered and washed with methanol to obtain 4.76g of the intermediate [21-C] (yield 42%).

[0576] (4) Synthesis of Compound 21

[0577] The intermediate [21-C] (1.0 eq) synthesized as described above, potassium tetrachloroplatinate (K 2 PtCl 4 ) (1.1 eq) and tetrabutylammonium bromide (0.1 eq) were dissolved in acetic acid (0.1 M) and stirred at a temperature of 120° C. for 72 hours. The reaction mixture was cooled to room temperature, and an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried and concentrated by using anhydrous magnesium sulfate, and column chromatography was performed thereon to obtain 1.35 g of compound 21 (yield 20%).

[0578] Table 1 shows the compositions of the compounds synthesized in Synthesis Examples 1 to 10. 1 H NMR and HR-EIMS.

[0579] Those skilled in the art can also easily recognize the synthesis methods of compounds other than the compounds shown in Table 1 by referring to the above-mentioned synthesis mechanism and method.

[0580] [Table 1]

[0581]

[0582]

[0583] [Example]

[0584] Example 1

[0585] Corning 15Ω / cm2 was used as the substrate and ITO anode. 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonicated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition apparatus.

[0586] Referring to the following compound, 2-TNATA was vacuum deposited on an ITO anode formed on an ITO glass substrate to form a film with a thickness of A hole injection layer of 100 mm thick is formed by vacuum depositing NPB on the hole injection layer. hole transport layer.

[0587] Bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS) and POPCPA (co-host) (BCPDS to POPCPA weight ratio: 1:1) and compound 1 (dopant) were co-deposited on the hole transport layer at a co-host to dopant weight ratio of 90:10 to form a layer with a thickness of 1000 nm. The emission layer.

[0588] TSPO1 is deposited on the emitter layer to form a A hole blocking layer is formed, and Alq is deposited on the hole blocking layer. 3 To form a thickness of The electron transport layer is formed by depositing LiF on the electron transport layer to form a layer with a thickness of An electron injection layer is formed by vacuum depositing Al on the electron injection layer to form a layer with a thickness of of the cathode, thereby completing the manufacture of the organic light-emitting device.

[0589]

[0590] Example 2 to Example 10

[0591] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were each used as a dopant instead of Compound 1 in forming the emission layer.

[0592] Comparative Examples 1 to 4

[0593] An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound A, Compound B, Compound C, and Compound D were each used as a dopant instead of Compound 1 in forming the emission layer.

[0594]

[0595]

[0596] The driving voltage, current density, brightness, luminous efficiency, and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 10 and Comparative Examples 1 to 4 were measured by using Keithley SMU 236 and a brightness meter PR650, and the results are shown in Table 2. The T95 lifetime represents the time (hours) for the brightness of the organic light-emitting device to decrease to 95% of its initial brightness.

[0597] [Table 2]

[0598]

[0599]

[0600] Referring to Table 2, it can be seen that compared with the driving voltage, efficiency, color purity and lifespan of the organic light-emitting devices of Comparative Examples 1 to Comparative Examples 4, the organic light-emitting devices of Examples 1 to 10 have low driving voltage, high efficiency, high color purity and long lifespan.

[0601] Therefore, when the compound according to the example embodiment is used as a material for an emission layer of an organic light emitting device, excellent effects may be exhibited in terms of driving voltage, efficiency, and lifespan, and a blue light emitting device having high color purity may be realized.

[0602] An organic light emitting device including an organic metal compound according to an exemplary embodiment may have low driving voltage, high efficiency, and high color purity. Therefore, an organic light emitting device having high quality may be realized.

[0603] Example embodiments have been disclosed herein, and although specific terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art as of the time of filing this application, unless otherwise specifically stated, features, characteristics, and / or elements described in conjunction with a specific embodiment may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments. Therefore, it will be understood by those skilled in the art that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the claims.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode, facing the first electrode; an organic layer located between the first electrode and the second electrode and including an emission layer; and At least one organometallic compound represented by Formula 1: <Formula 1> Among them, in formula 1, From the formula 1 The part represented by is expressed by formula 1-2: <Formula 1-2> * indicates the same as B in formula 1 12 and B 13 The binding position of *' represents the same as (L1) in formula 1 a1 The binding site of *" indicates the same as (L2) in formula 1 a2 The binding site M 11 is selected from platinum, palladium, copper, zinc, silver, gold, rhodium, iridium, ruthenium, rhenium, osmium, titanium, zirconium, hafnium, europium, terbium and thulium, Ring A 11 and Ring A 14 are independently selected from C5-C 60 Carbocyclic and C1-C 60 Heterocyclic group, Y 11 and Y 14 are independently selected from carbon atoms and nitrogen atoms, and Y 11 and Y 14 At least one of them is a carbon atom, B 11 To B 14 are independently selected from a single bond, *-O-*' and *-S-*', L1 to L3 are independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*'、*-C(R 16 )=*'、*=C(R 16 )-*'、*-C(R 16 )=C(R 17 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*'、*-N(R 16 )-*'、*-P(R 16 )-*'、*-Si(R 16 )(R 17 )-*' and *-Ge(R 16 )(R 17 )-*', a1 to a3 are independently selected from 0, 1, 2 and 3, provided that at least two selected from a1 to a3 are independently selected from 1, 2 and 3, When a1 is 0, ring A 11 and Ring A 12 Not connected, when a2 is 0, ring A 13 and Ring A 14 Not connected, and when a3 is 0, ring A 11 and Ring A 14 Not connected, X1 and X2 are independently selected from O and S, R 11 and R 14 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -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), b11 and b14 are each independently an integer from 1 to 10, R 41 To R 47 are independently selected from hydrogen and deuterium, The substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -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 )和-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, * and *' both represent the binding sites with adjacent atoms. B represents a boron atom, and Ring A 11 Through Ring A 11 The nitrogen atom is attached to ring A 12 and / or Ring A 14 Through Ring A 14 The nitrogen atom is attached to ring A 13 .

2. The organic light emitting device according to claim 1, wherein: The emissive layer includes the at least one organometallic compound.

3. The organic light emitting device according to claim 2, wherein: The emission layer further includes a host, and the at least one organic metal compound is included in the emission layer in an amount of 0.01 parts by weight to 30 parts by weight based on 100 parts by weight of the emission layer.

4. The organic light emitting device according to claim 3, wherein: The main body includes two different main bodies.

5. The organic light emitting device according to claim 1, wherein: The emissive layer includes the at least one organometallic compound, and The emission layer emits blue light having a maximum emission wavelength of 430 nm to 490 nm.

6. The organic light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

7. The organic light emitting device according to claim 6, wherein: The electron transport region includes a phosphine oxide-containing compound or a silyl group-containing compound.

8. An organometallic compound, the organometallic compound is represented by Formula 1: <Formula 1> in, In formula 1, From the formula 1 The part represented by is expressed by formula 1-2: <Formula 1-2> * indicates the same as B in formula 1 12 and B 13 The binding position of *' represents the same as (L1) in formula 1 a1 The binding site of *" indicates the same as (L2) in formula 1 a2 The binding site M 11 is selected from platinum, palladium, copper, zinc, silver, gold, rhodium, iridium, ruthenium, rhenium, osmium, titanium, zirconium, hafnium, europium, terbium and thulium, Ring A 11 and Ring A 14 are independently selected from C5-C 60 Carbocyclic and C1-C 60 Heterocyclic group, Y 11 and Y 14 are independently selected from carbon atoms and nitrogen atoms, and Y 11 and Y 14 At least one of them is a carbon atom, B 11 To B 14 are independently selected from a single bond, *-O-*' and *-S-*', L1 to L3 are independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*'、*-C(R 16 )=*'、*=C(R 16 )-*'、*-C(R 16 )=C(R 17 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 16 )-*'、*-N(R 16 )-*'、*-P(R 16 )-*'、*-Si(R 16 )(R 17 )-*' and *-Ge(R 16 )(R 17 )-*', a1 to a3 are independently selected from 0, 1, 2 and 3, wherein at least two selected from a1 to a3 are independently selected from 1, 2 and 3, When a1 is 0, ring A 11 and Ring A 12 Not connected, when a2 is 0, ring A 13 and Ring A 14 Not connected, and when a3 is 0, ring A 11 and Ring A 14 Not connected, X1 and X2 are independently selected from O and S, R 11 and R 14 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -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), b11 and b14 are each independently an integer from 1 to 10, R 41 To R 47 are independently selected from hydrogen and deuterium, The substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic 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 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -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 )和-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, * and *' both represent the binding sites with adjacent atoms. B represents a boron atom, and Ring A 11 Through Ring A 11 The nitrogen atom is attached to ring A 12 and / or Ring A 14 Through Ring A 14 The nitrogen atom is attached to ring A 13 .

9. The organometallic compound according to claim 8, wherein M 11 Selected from Pt, Pd, Cu, Ag and Au.

10. The organometallic compound according to claim 8, wherein Ring A 11 and Ring A 14 are independently selected from benzene, naphthalene, anthracene, phenanthrene, azulene, benzo[9,10]phenanthrene, pyrene, Cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, furan, thiophene, silole, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilole, dibenzosilole, indenopyridine, indolepyridine, benzofuranopyridine, benzothienopyridine, benzothiorrolopyridine, indenopyrimidine, indolepyrimidine, benzofuranopyrimidine, benzothienopyrimidine, benzothiorrolopyrimidine, dihydropyridine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline , pyrrole, pyrazole, imidazole, 2,3-dihydroimidazole, triazole, 2,3-dihydrotriazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, 2,3-dihydrobenzimidazole, imidazopyridine, 2,3-dihydroimidazopyridine, imidazopyrimidine, 2,3-dihydroimidazopyrimidine, imidazopyrazine, 2,3-dihydroimidazopyrazine, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

11. The organometallic compound according to claim 8, wherein Ring A 11 and Ring A 14 are independently selected from the groups represented by Formula 2-1(1) to Formula 2-1(27) and Formula 2-2(1) to Formula 2-2(20): Among them, in Formula 2-1(1) to Formula 2-1(27) and Formula 2-2(1) to Formula 2-2(20), Y 15 is Y in formula 1 11 or Y 14 , X 21 is N or C(R 21 ), X 22 is N or C (R 22 ), X 23 is N or C(R 23 ), X 24 is N or C (R 24 ), X 25 is N or C (R 25 ), X 26 is N or C (R 26 ), X 27 is N or C(R 27 ), and X 28 is N or C(R 28 ), X 29 is C(R 29a )(R 29b ), N(R 29 ), O, S or Si(R 29a )(R 29b ), R 21 To R 29 and R 25a To R 29b are independently combined with R in formula 1 11 and R 14 Same as described, * indicates the same as B in formula 1 11 or B 14 The binding position of *' represents the same as (L1) in formula 1 a1 or (L2) a2 The binding site of *" indicates the same as (L3) in Formula 1 a3 The combination position.

12. The organometallic compound according to claim 8, wherein Ring A 11 and Ring A 14 are independently selected from the groups represented by Formula 3-1(1) to Formula 3-1(38) and Formula 3-2(1) to Formula 3-2(23): Among them, in Formula 3-1(1) to Formula 3-1(38) and Formula 3-2(1) to Formula 3-2(23), Y 15 is Y in formula 1 11 or Y 14 , X 29 is C(R 29a )(R 29b ), N(R 29 ), O, S or Si(R 29a )(R 29b ), R 29 , R 29a , R 29b , R 31 and R 32 are independently combined with R in formula 1 11 and R 14 Same as described, b32 is 1 or 2, b33 is 1, 2, or 3, b34 is 1, 2, 3, or 4, b35 is 1, 2, 3, 4, or 5, b36 is 1, 2, 3, 4, 5, or 6, * indicates the same as B in formula 1 11 or B 14 The binding position of *' represents the same as (L1) in formula 1 a1 or (L2) a2 The binding site of *" indicates the same as (L3) in Formula 1 a3 The combination position.

13. The organometallic compound according to claim 8, wherein: ii) Y 11 is C, and M 11 With Y 11 The key between or B 11 With Y 11 The bond between them is a coordination bond; iii) Y 14 is C, and M 11 With Y 14 The key between or B 14 With Y 14 The bond between is a coordination bond; or iv) Y 11 and Y 14 Both C, M 11 With Y 11 The key between or B 11 With Y 11 The bond between is a coordination bond, and M 11 With Y 14 The key between or B 14 With Y 14 The bond between them is a coordination bond.

14. The organometallic compound according to claim 8, wherein: B 11 To B 14 is a single bond, and From M 11 With Y 11 The key between 11 With Y 12 The key between 11 With Y 13 The key between M 11 With Y 14 Two bonds selected among the bonds between are coordinate bonds, and the other bonds among them are covalent bonds.

15. The organometallic compound according to claim 8, wherein L1 and L2 are both single bonds, a1 and a2 are both 1, and a3 is 0.

16. The organometallic compound according to claim 8, wherein R 11 and R 14 are independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy; C1-C1-C2-substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano, phenyl and biphenyl 20 Alkyl and C1-C 20 Alkoxy; and A group represented by one selected from Formula 5-1 to Formula 5-25 and Formula 6-1 to Formula 6-55: Among them, in Formula 5-1 to Formula 5-25 and Formula 6-1 to Formula 6-55, Y 31 is O, S, C(Z 34 )(Z 35 ), N(Z 34 ) or Si(Z 34 )(Z 35 ), Z 31 To Z 35 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkenyl, C1-C 20 Alkynyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl and triazinyl, e2 is 1 or 2, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is an integer from 1 to 5, e6 is an integer from 1 to 6, e7 is an integer from 1 to 7, e9 is an integer from 1 to 9, and *Indicates the binding site with the adjacent atom.

17. The organometallic compound according to claim 8, wherein The organometallic compound is selected from Compound 1, Compound 3 to Compound 5, Compound 8 to Compound 11, Compound 13 to Compound 20, and Compound 23 to Compound 25:

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