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

Abstract

Provided are an organic metal compound and an organic light-emitting device including the organic metal compound. The organic metal compound is represented by Formula 1. 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.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0064072 filed on May 30, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more embodiments relate to an organometallic compound and an organic light emitting device including the organometallic compound. Background Art

[0003] Compared with other devices in the art, the organic light emitting device is a self-emissive device that produces full-color images and also has wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.

[0004] The organic light-emitting device may include a first electrode located on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially located 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 transition (e.g., transition or relaxation) from an excited state to a ground state, thereby generating light. Summary of the invention

[0005] One or more embodiments include an organometallic compound and an organic light emitting device including the organometallic compound.

[0006] Additional aspects of the embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.

[0007] One aspect of an embodiment of the present disclosure provides an organometallic compound represented by Formula 1:

[0008] Formula 1

[0009] ML A L B .

[0010] In formula 1,

[0011] M may be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), iridium (Ir), rhodium (Rh), cobalt (Co), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm),

[0012] L Amay be a tridentate ligand represented by Formula 1A, and

[0013] L B It may be a tridentate ligand represented by Formula 1B:

[0014] Formula 1A

[0015]

[0016] Formula 1B

[0017]

[0018] In Formula 1A and Formula 1B,

[0019] Ring A 1 Can include Y 1 A five-membered ring including Y 1 The five-membered ring with at least one C 5 -C 60 A carbocyclic condensed polycyclic group, or a group including Y 1 The five-membered ring with at least one C 1 -C 60 Heterocyclic condensed polycyclic groups,

[0020] Ring A 2 To Ring A 6 can be independently selected from C 5 -C 60 Carbon ring and C 1 -C 60 Heterocyclic rings,

[0021] Y 1 To Y 6 can all independently be N or C,

[0022] L 1 and L 2 can be independently selected from *-O-*', *-S-*', *-C(R 7 )(R 8 )-*'、*-C(R 7 )=*'、*=C(R 7 )-*'、*-C(R 7 )=C(R 8 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 7 )-*'、*-N(R 7 )-*'、*-P(R 7 )-*'、*-Si(R 7 )(R 8)-*'、*-P(R 7 )(R 8 )-*' and *-Ge(R 7 )(R 8 )-*',

[0023] n1 may be selected from 1, 2 and 3, and n2 may be selected from 0, 1, 2 and 3,

[0024] R 1 To R 8 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, 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 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 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),

[0025] b1 number of R 1 Two adjacent R 1 , b2 number of R 2 Two adjacent R 2 , b3 number of R 3 Two adjacent R 3 , b4 number of R 4 Two adjacent R 4 , b5 number of R 5 Two adjacent R 5 , b6 number of R 6 Two adjacent R 6 and R 1 With R 7 , R 2 With R 7 and R 3 With R 7 At least one of the groups may be optionally linked to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0026] b1 to b6 may each independently be an integer from 1 to 10,

[0027] * indicates the binding site with M,

[0028] 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 C6 -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:

[0029] 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;

[0030] 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 C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C60 Alkoxy;

[0031] 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;

[0032] 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)(Q21 )(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

[0033] -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

[0034] 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, C1 -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.

[0035] Another aspect of an embodiment of the present disclosure provides 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 organic metal compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] These and / or other aspects of the embodiments will become apparent and more easily understood through the following description of the embodiments in conjunction with the accompanying drawings, in which:

[0037] Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment;

[0038] Figure 2 is a schematic diagram of an organic light emitting device according to another embodiment;

[0039] Figure 3 is a schematic diagram of an organic light emitting device according to another embodiment; and

[0040] Figure 4 is a schematic diagram of an organic light emitting device according to another embodiment. DETAILED DESCRIPTION

[0041] Now will refer to embodiment in more detail, the example of embodiment is shown in the accompanying drawings, wherein the same reference numerals refer to the same element from time to time. In this regard, the current embodiment can have different forms, and should not be construed as being limited to the description set forth herein. Therefore, hereinafter only the embodiment is described herein by reference to the accompanying drawings to explain the various aspects of the embodiment of this description. As used herein, the term "and / or" includes any combination and all combinations of one or more related listed items. When the expression such as "at least one (kind / person) of ... " is after a row of elements (elements), what is modified is the element (element) of the entire row, rather than modifying the individual element (element) in the row.

[0042] The organometallic compound according to an embodiment may be represented by Formula 1:

[0043] Formula 1

[0044] ML A L B .

[0045] In Formula 1, M may be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), iridium (Ir), rhodium (Rh), cobalt (Co), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).

[0046] In one embodiment, M may be iridium or rhodium.

[0047] In formula 1, L A It may be a tridentate ligand represented by Formula 1A, L B It may be a tridentate ligand represented by Formula 1B:

[0048] Formula 1A

[0049]

[0050] Formula 1B

[0051]

[0052] In Formula 1A, Ring A 1 Can include Y 1 A five-membered ring including Y 1 The five-membered ring with at least one C 5 -C 60 A carbocyclic condensed polycyclic group, or a group including Y 1 The five-membered ring with at least one C 1 -C 60 Heterocyclic condensed polycyclic group.

[0053] In Formula 1A, The group represented by may be selected from the groups represented by formula A1-1 to formula A1-7:

[0054]

[0055] In Formula A1-1 to Formula A1-7,

[0056] X 11 It can be C(R 11 ) or N, X 12 It can be C(R 12 ) or N, X 13 It can be C(R 13 ) or N, X 14 It can be C(R 14 ) or N, X 15 It can be C(R 15 ) or N, X 16It can be C(R 16 ) or N, and X 17 It can be C(R 17 ) or N,

[0057] X 18 It can be C(R 18 )(R 19 )、Si(R 18 )(R 19 )、N(R 18 )、P(R 18 ), O or S,

[0058] R 11 To R 19 can be independently combined with R 1 are defined the same as

[0059] * indicates the binding site with M, *' indicates the binding site with (L 1 ) n1 The combination position.

[0060] In one embodiment, in Formula A1-1 to Formula A1-7, R 11 To R 19 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 10 Alkyl, C substituted with at least one -F 1 -C 10 Alkyl, C substituted with at least one -Cl 1 -C 10 Alkyl, C substituted with at least one -Br 1 -C 10 Alkyl, C substituted with at least one -I 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl.

[0061] In one embodiment, the The group represented by can be represented by formula A1-1, X 11 It can be C(R 11 ), X 12 It can be C(R 12 ), and X 13 Can be N.

[0062] In one embodiment, the The group represented by can be represented by formula A1-1, X 11 Can be N, X 12 It can be C(R 12 ), and X 13 Can be N.

[0063] In one embodiment, the The group represented by can be represented by formula A1-1, X 11 It can be C(R 11 ), X 12 It can be C(R 12 ), X 13 Can be N, and R 11 and R 12 At least one of them can be selected from cyano, C substituted with at least one -F 1 -C 10 Alkyl, C substituted with at least one -Cl 1 -C 10 Alkyl, C substituted with at least one -Br 1 -C 10 Alkyl and C substituted with at least one -I 1 -C 10 Alkyl. For example, R 11 and R 12 At least one of them can be cyano or -CF 3 In another embodiment, the The group represented by can be represented by formula A1-1, X 11 Can be N, X 12 It can be C(R 12 ), X 13 Can be N, and R 12 Can be selected from cyano, C substituted with at least one -F 1 -C 10 Alkyl, C substituted with at least one -Cl 1 -C 10 Alkyl, C substituted with at least one -Br 1 -C 10 Alkyl and C substituted with at least one -I 1 -C 10 Alkyl. For example, R 12 Can be cyano or -CF 3 .

[0064] In Formula 1A and Formula 1B, Ring A 2 To Ring A 6 can be independently selected from C 5 -C 60 Carbon ring and C 1 -C60 Heterocyclic ring.

[0065] In one embodiment, in Formula 1A and Formula 1B, Ring A 3 , Ring A 4 and Ring A 6 can be independently selected from the groups represented by Formula 2-1(1) to Formula 2-1(27), Ring A 2 and Ring A 5 Each may be independently selected from the groups represented by Formula 2-2(1) to Formula 2-2(19):

[0066]

[0067]

[0068] In Formula 2-1(1) to Formula 2-1(27) and Formula 2-2(1) to Formula 2-2(19),

[0069] Y 15 can be N or C bonded to M,

[0070] 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 (R 27 ), and X 28 Can be N or C (R 28 ),

[0071] X 29 It can be C(R 29a )(R 29b )、Si(R 29a )(R 29b )、N(R 29 ), O or S,

[0072] Z 21 and Z 22 can all independently be N or P,

[0073] R 21 To R 30 , R 25a To R 29aand R 25b To R 29b can be independently related to R 2 To R 6 The same definition,

[0074] * indicates the binding site with M, and

[0075] *' and *" both indicate the binding site with the adjacent atom.

[0076] In one embodiment, in Formula 1A and Formula 1B, Ring A 2 and Ring A 5 may be independently a group represented by formula 2-2(1), ring A 3 It may be a group represented by formula 2-1(1), wherein ring A 4 and Ring A 6 Each may be independently a group represented by Formula 2-1(17) or Formula 2-1(26).

[0077] In one embodiment, in Formula 1A, Ring A 1 It may be a group represented by formula A1-11 or A1-12, wherein ring A 2 It may be a group represented by formula A2-11 or A2-12, wherein ring A 3 It may be a group represented by formula A3-11, formula A3-12 or formula A3-13:

[0078]

[0079] In Formula A1-11, Formula A1-12, Formula A2-11, Formula A2-12, and Formula A3-11 to Formula A3-13,

[0080] Y 2 , Y 3 , R 11 , R 12 , R 2 and R 3 may each independently be the same as described herein,

[0081] b21 and b32 may each independently be an integer from 1 to 3,

[0082] b22 can be 1 or 2,

[0083] b31 can be an integer from 1 to 4.

[0084] * indicates the binding site with M,

[0085] *' indicates the same as (L 1 ) n1 The binding site of

[0086] *" indicates the same as (L 2 ) n2 The combination position.

[0087] In Formula 1A and Formula 1B, Y 1 To Y 6 Each may independently be N or C.

[0088] In one embodiment, in Formula 1A, Y 1 and Y 2 Can be N, Y 3 It can be C,

[0089] Y 1 The bond between M can be a covalent bond,

[0090] Y 2 The bond between M and

[0091] Y 3 The bond with M may be a covalent bond.

[0092] In one or more embodiments, in Formula 1B, Y 4 and Y 6 Can be C, Y 4 The bond between M and Y 6 The bonds with M may all be coordination bonds.

[0093] In one or more embodiments, in Formula 1B, Y 4 and Y 6 Can be N, Y 4 The bond between M and Y 6 The bonds with M may all be coordination bonds.

[0094] In one or more embodiments, in Formula 1B, Y 4 To Y 6 Can be C, Y 4 The bond between M and Y 6 The bonds between Y and M can all be coordination bonds. 5 The bond with M may be a covalent bond.

[0095] In one or more embodiments, in Formula 1B, Y 4 and Y 6 Can be N, Y 5 Can be C, Y 4 The bond between M and Y 6 The bonds between Y and M can all be coordination bonds. 5 The bond with M may be a covalent bond.

[0096] In Formula 1A, L 1and L 2 can be independently selected from *-O-*', *-S-*', *-C(R 7 )(R 8 )-*'、*-C(R 7 )=*'、*=C(R 7 )-*'、*-C(R 7 )=C(R 8 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 7 )-*'、*-N(R 7 )-*'、*-P(R 7 )-*'、*-Si(R 7 )(R 8 )-*'、*-P(R 7 )(R 8 )-*' and *-Ge(R 7 )(R 8 )-*'.

[0097] In Formula 1A, n1 may be selected from 1, 2 and 3, and n2 may be selected from 0, 1, 2 and 3. When n2 is 0, by *-(L 2 ) n2 The bond represented by -*' can be a single bond. 2 and Ring A 3 Can connect via one-touch.

[0098] In one embodiment, n1 may be 1 and n2 may be 0; or n1 may be 1 and n2 may be 1.

[0099] In one embodiment, n1 may be 1, n2 may be 0, and L 1 Can be selected from *-O-*', *-S-*', *-C(R 7 )(R 8 )-*'、*-B(R 7 )-*'、*-N(R 7 )-*' and *-Si(R 7 )(R 8 )-*'.

[0100] In one or more embodiments, n1 may be 1, n2 may be 1, L 1 and L 2 can be independently selected from *-O-*', *-S-*', *-C(R 7 )(R 8 )-*'、*-B(R 7 )-*' and *-N(R 7 )-*'.

[0101] For example, n1 and n2 can both be 1, and

[0102] L 1 It can be *-O-*', and L 2 Can be *-O-*',

[0103] L 1 Can be *-C(R 7 )(R 8 )-*', and L 2 Can be *-O-*',

[0104] L 1 Can be *-N(R 7 )-*', and L 2 Can be *-O-*',

[0105] L 1 Can be *-S-*', and L 2 Can be *-O-*',

[0106] L 1 Can be *-B(R 7 )-*', and L 2 Can be *-O-*',

[0107] L 1 It can be *-Si(R 7 )(R 8 )-*', and L 2 Can be *-O-*',

[0108] L 1 It can be *-O-*', and L 2 Can be *-N(R 7 )-*',

[0109] L 1 Can be *-C(R 7 )(R 8 )-*', and L 2 Can be *-N(R 7 )-*',

[0110] L 1 Can be *-N(R 7 )-*', and L 2 Can be *-N(R 7 )-*',

[0111] L 1 Can be *-S-*', and L 2 Can be *-N(R7 )-*',

[0112] L 1 Can be *-B(R 7 )-*', and L 2 Can be *-N(R 7 )-*',or

[0113] L 1 It can be *-Si(R 7 )(R 8 )-*', and L 2 Can be *-N(R 7 )-*'.

[0114] In one embodiment, in Formula 1, L A It may be a group represented by Formula 1C:

[0115] Formula 1C

[0116]

[0117] In Formula 1C,

[0118] Ring A 1 , Ring A 2 , Y 1 To Y 3 , L 1 、n1、R 1 , R 2 , b1 and b2 may all independently be the same as described herein,

[0119] X 31 It can be C(R 31 ) or N, X 32 It can be C(R 32 ) or N, X 33 It can be C(R 33 ) or N, X 34 It can be C(R 34 ) or N, X 35 It can be C(R 35 ) or N, X 36 It can be C(R 36 ) or N, and X 37 It can be C(R 37 ) or N,

[0120] R 31 To R 37 can be independently combined with R in formula 1A 3 are defined the same as

[0121] * indicates the binding site with M.

[0122] In one embodiment, in Formula 1C, X 31 It can be C(R 31 ), X 32 It can be C(R 32 ) or N, X 33 It can be C(R 33 ), X 34 It can be C(R 34 ), X 35 It can be C(R 35 ) or N, X 36 It can be C(R 36 ), and X 37 It can be C(R 37 ),

[0123] R 31 , R 33 , R 34 , R 36 and R 37 may all independently be hydrogen,

[0124] R 32 and R 35 can be independently selected from hydrogen, cyano, methyl, -CF 3 , -CCl 3 , -CBr 3 、-CI 3 , ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and phenyl.

[0125] In one or more embodiments, in Formula 1C, X 31 It can be C(R 31 ), X 32 It can be C(R 32 ) or N, X 33 It can be C(R 33 ), X 34 It can be C(R 34 ), X 35 It can be C(R 35 ) or N, X 36 It can be C(R 36 ), and X 37 It can be C(R 37 ),

[0126] R 31 , R 33 , R 34 , R 36 and R 37 may each independently be hydrogen, and

[0127] R 32and R 35 can be independently selected from cyano and -CF 3 .

[0128] In one embodiment, in Formula 1, L B It may be a group represented by Formula 1B-11 or Formula 1B-12:

[0129]

[0130] In Formula 1B-11 and Formula 1B-12,

[0131] Y 5 , Ring A 5 , R 5 and b5 may each independently be the same as described herein,

[0132] Z 41 To Z 44 can all independently be N or P,

[0133] X 41 It can be C(R 41 ) or N, X 42 It can be C(R 42 ) or N, X 43 It can be C(R 43 ) or N, and X 44 It can be C(R 44 ) or N,

[0134] R 41 To R 46 can be independently combined with R in formula 1B 4 and R 6 are defined identically, and

[0135] * indicates the binding site with M.

[0136] In one embodiment, in Formula 1B-11 and Formula 1B-12, Z 41 To Z 44 Both can be N.

[0137] In one embodiment, in Formula 1, L B It may be a group represented by Formula 1B-21 or Formula 1B-22:

[0138]

[0139] In Formula 1B-21 and Formula 1B-22,

[0140] Y 5 , X 41 To X 44 and R 45and R 46 may each independently be the same as described herein,

[0141] X 51 It can be C(R 51 ) or N, X 52 It can be C(R 52 ) or N, and X 53 It can be C(R 53 ) or N,

[0142] R 51 To R 53 can be independently combined with R in formula 1B 5 are defined the same as

[0143] * indicates the binding site with M.

[0144] In one embodiment, in Formula 1B-21 and Formula 1B-22, X 51 It can be C(R 51 ), X 52 It can be C(R 52 ), and X 53 It can be C(R 53 ),and

[0145] R 51 To R 53 can be independently selected from hydrogen, cyano, methyl, -CF 3 , -CCl 3 , -CBr 3 、-CI 3 , ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and phenyl.

[0146] In Formula 1A and Formula 1B, R 1 To R 8 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, 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 10Heterocycloalkyl, 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 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), where Q 1 To Q 3 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 groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.

[0147] b1 number of R 1 Two adjacent R1 , b2 number of R 2 Two adjacent R 2 , b3 number of R 3 Two adjacent R 3 , b4 number of R 4 Two adjacent R 4 , b5 number of R 5 Two adjacent R 5 , b6 number of R 6 Two adjacent R 6 and R 1 With R 7 , R 2 With R 7 and R 3 With R 7 At least one of the groups may be optionally linked to form a substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group.

[0148] In one embodiment, R in Formula 1A and Formula 1B 1 To R 8 Can be independently selected from:

[0149] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0150] 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;

[0151] Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, spirofluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl , acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiolaryl, benzothiazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, dibenzothiolaryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridyl, imidazopyrimidyl, oxazolopyridyl, thiazolopyridyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzothiolaryl, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 ) and -B(Q 1 )(Q 2 );as well as

[0152] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, naphthyl, fluorenyl, spirobifluorenyl, spirofluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenanthene, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrrolyl, thienyl, furanyl, thirol, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrene pyridinyl, pyrimidinyl, oxazolidinyl, pyrimid ... at least one of cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, spirofluorene-benzofluorenyl, benzofluorenyl, dibenzofluorenyl, pyrenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrrolyl, thienyl, furanyl, thirolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolyl, isoindolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthroline, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiolaryl, benzothiazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, dibenzothiolaryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspirobifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl and azadibenzothiolaryl, wherein Q 1 To Q 3 May be the same as described herein above.

[0153] In one or more embodiments, R in Formula 1A and Formula 1B 1 To R 8 Can be independently selected from:

[0154] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0155] 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;

[0156] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl, and triazinyl; and

[0157] All are substituted with deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, -CF 3 , -CCl 3 , -CBr 3 、-CI 3 , phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl and triazinyl, and at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, phenanthryl, anthracenyl, pyridyl, pyrimidinyl, carbazolyl and triazinyl.

[0158] In one or more embodiments, R in Formula 1A and Formula 1B 1 To R 8 Can be independently selected from:

[0159] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, -CF 3 , -CCl 3 , -CBr 3 、-CI 3 , ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl;

[0160] phenyl and pyridyl; and

[0161] All are substituted with deuterium, -F, -Cl, -Br, -I, cyano, methyl, -CF 3 , -CCl 3 , -CBr 3 、-CI 3at least one selected from the group consisting of phenyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0162] In one embodiment, the R of the number from b1 1 , b2 number of R 2 , b3 number of R 3 , b4 number of R 4 , b5 number of R 5 and b6 numbers of R 6 At least one of the selected groups may be an electron withdrawing group. 1 , b2 number of R 2 , b3 number of R 3 , b4 number of R 4 , b5 number of R 5 and b6 numbers of R 6 At least one of the selected ones can be selected from cyano, C substituted with at least one -F 1 -C 10 Alkyl, C substituted with at least one -Cl 1 -C 10 Alkyl, C substituted with at least one -Br 1 -C 10 Alkyl and C substituted with at least one -I 1 -C 10 alkyl.

[0163] In one or more embodiments, the R of the number from b1 1 , b2 number of R 2 , b3 number of R 3 , b4 number of R 4 , b5 number of R 5 and b6 numbers of R 6 At least one of the groups selected from may be selected from cyano, -CF 3 , -CCl 3 , -CBr 3 and-CI 3 For example, from b1, the number of R 1 , b2 number of R 2 , b3 number of R 3 , b4 number of R 4 , b5 number of R 5 and b6 numbers of R 6 At least one selected from cyano and -CF 3 .

[0164] When the organometallic compound represented by Formula 1 includes at least one electron withdrawing group such as a cyano group, the emission wavelength of the organometallic compound may be shifted to a shorter wavelength (blue shift), thus emitting blue light with high color purity.

[0165] In Formula 1A and Formula 1B, b1 to b6 may each independently be an integer of 1 to 10.

[0166] In one embodiment, the organometallic compound can be selected from Compound 1 to Compound 66:

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] When ring A in formula 1A 2 is a pyridine ring (where Y 2 When N), ring A 2 Most of the lowest unoccupied molecular orbital (LUMO) of (or Formula 1A) is distributed in the pyridine portion. Since the organometallic compound represented by Formula 1 includes a tridentate ligand L A (Among them, Ring A 1 and Ring A 3 Covalently bound to ring A 2 on both sides (or covalently bonded to ring A 2 on both sides)), so it can improve the ring A 2 The stability of the bond between the ring A and the metal center M. For example, 2 The stability of the bond between the metal center M can be enhanced to increase the transition (e.g., transition) of the organometallic compound from the triplet state to the metal center state ( 3 In some embodiments, ring A 2 The stability of the bond between the metal center M is improved, which increases the 3 Therefore, the lifetime of the organic metal compound can be improved, and an organic light emitting device including the organic metal compound can have a long lifetime.

[0174] In the organometallic compound represented by Formula 1, since ring A 1 and Ring A 2 In the tridentate ligand L AIn the example, ring A is connected via a linker other than a single bond. 1 and Ring A 2 The π conjugation between them is reduced, which helps to adjust the LUMO energy level. Therefore, the emission wavelength of the organic metal compound can be shifted to a shorter wavelength, so that the organic metal compound is configured to emit blue light with high color purity. In addition, by appropriately selecting L in Formula 1A 1 and L 2 , which can help to adjust the emission wavelength of the organometallic compound.

[0175] Since the organometallic compound represented by Formula 1 further includes a tridentate ligand L B , so the highest occupied molecular orbital (HOMO) energy level increases to shift the emission wavelength of the organic metal compound to a shorter wavelength (blue shift), so that the organic metal compound is configured to emit blue light with high color purity.

[0176] In addition, the organic metal compound according to one or more embodiments may include at least one electron withdrawing group in the molecule. Therefore, the emission wavelength of the organic metal compound is shifted to a shorter wavelength (blue shift), so that the organic metal compound is configured to emit blue light with high color purity.

[0177] The synthesis method for the organometallic compound represented by Formula 1 will be apparent to one of ordinary skill in the art by referring to the following examples.

[0178] The organometallic compound represented by Formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound can be included in an emission layer. The organometallic compound can act as a dopant in the emission layer. In one or more embodiments, the organometallic compound of Formula 1 can be used as a material for a cap layer located outside a pair of electrodes of an organic light-emitting device.

[0179] Therefore, another aspect of an embodiment of the present disclosure provides 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 organic metal compound represented by Formula 1.

[0180] In one embodiment, the organic layer of the organic light emitting device may include at least one organic metal compound represented by Formula 1.

[0181] The expression “(organic layer) includes at least one organometallic compound” as used herein may include the case where “(organic layer) includes the same organometallic compound represented by Formula 1” and the case where “(organic layer) includes two or more different organometallic compounds represented by Formula 1”.

[0182] For example, the organic layer may include only compound 1 as an organic metal compound. In this regard, compound 1 may be present only in the emission layer of the organic light-emitting device. In one or more 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 (for example, compound 1 and compound 2 may both be present in the emission layer), or may be present in different layers (for example, compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport region).

[0183] In one or more embodiments, the emission layer of the organic light emitting device may include an organometallic compound.

[0184] In one or more embodiments, the emission layer of the organic light-emitting device may include an organic metal compound and may further include a host. Here, 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. For example, based on 100 parts by weight of the emission layer, the amount of the organic metal compound may be in the range of about 0.01 parts by weight to about 30 parts by weight.

[0185] In one embodiment, the emission layer may include an organic metal compound and may be configured to emit blue light or green light. In one embodiment, the emission layer may include an organic metal compound and may be configured to emit light having a maximum emission wavelength of about 450 nm or more and about 550 nm or less. For example, the emission layer may be configured to emit blue light having a maximum emission wavelength of about 460 nm or more and about 480 nm or less.

[0186] The maximum emission wavelength of the organometallic compound is obtained by using a photoluminescence (PL) measurement instrument.

[0187] In one embodiment, the first electrode may be an anode, the second electrode may be a cathode, the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, the hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0188] In one embodiment, a hole transport region of an organic light emitting device may include a p-dopant having a LUMO level of about −3.5 eV or less.

[0189] As used herein, the term "organic layer" refers to a single layer and / or multiple layers located between the first electrode and the second electrode of the organic light-emitting device. The material included in the "organic layer" is not limited to an organic material. For example, the organic layer may include an inorganic material.

[0190] Figure 1 Description

[0191] Figure 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0192] 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 an embodiment are described.

[0193] First electrode 110

[0194] exist Figure 1 In the embodiment, the substrate may be additionally located below the first electrode 110 or above 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, ease of handling, and waterproofness.

[0195] 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.

[0196] 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, the material used to form the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.

[0197] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0198] Organic layer 150

[0199] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emission layer.

[0200] 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 .

[0201] Hole transport region in the organic layer 150

[0202] 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.

[0203] 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.

[0204] For example, the hole transport region may have a single-layer structure or a multi-layer structure, wherein the single-layer structure includes a single layer comprising a plurality of different materials, and the multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the first electrode 110 in the order stated, but the structure of the hole transport region is not limited thereto.

[0205] 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), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0206]

[0207] Formula 201

[0208]

[0209] Formula 202

[0210]

[0211] In equation 201 and equation 202,

[0212] 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,

[0213] 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,

[0214] xa1 to xa4 may each independently be an integer from 0 to 3,

[0215] xa5 can be an integer from 1 to 10, and

[0216] R 201 To R 204and 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 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0217] For example, in Equation 202, R 201 and R 202 can be optionally linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, R 203 and R 204 The groups may alternatively be linked to each other via single bonds, dimethyl-methylene groups or diphenyl-methylene groups.

[0218] In one embodiment, in equation 201 and equation 202,

[0219] L 201 To L 205 Can be independently selected from:

[0220] 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

[0221] 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

[0222] 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.

[0223] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.

[0224] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0225] In one or more embodiments, R 201 To R 204 and Q201 Can be independently selected from:

[0226] 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

[0227] 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

[0228] Q 31 To Q 33 Same as described here above.

[0229] In one or more embodiments, from R in Formula 201 201 To R 203 At least one of the selected ones can be independently selected from:

[0230] fluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

[0231] 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 an alkyl group selected from the group consisting of 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 dibenzothiophenyl group,

[0232] However, the embodiments of the present disclosure are not limited thereto.

[0233] In one or more embodiments, in Formula 202, i) R 201 and R 202 can be linked to each other via a single bond, and / or ii) R 203 and R 204 can be connected to each other via a single bond.

[0234] In one or more embodiments, from R in Formula 202 201 To R 204 At least one of the selected ones may be selected from:

[0235] carbazolyl; and

[0236] 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 10a carbazolyl group selected from at least one of a phenyl group of an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

[0237] However, the embodiments of the present disclosure are not limited thereto.

[0238] The compound represented by Formula 201 may be represented by the following Formula 201-1, but embodiments of the present disclosure are not limited thereto:

[0239] Formula 201-1

[0240]

[0241] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201-2, but the embodiments of the present disclosure are not limited thereto:

[0242] Formula 201-2

[0243]

[0244] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201-2(1), but the embodiments of the present disclosure are not limited thereto:

[0245] Formula 201-2(1)

[0246]

[0247] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0248] Formula 201A

[0249]

[0250] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:

[0251] Formula 201A(1)

[0252]

[0253] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:

[0254] Formula 201A-1

[0255]

[0256] In one embodiment, the compound represented by Formula 202 may be represented by the following Formula 202-1, but embodiments of the present disclosure are not limited thereto:

[0257] Formula 202-1

[0258]

[0259] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202-1(1), but the embodiments of the present disclosure are not limited thereto:

[0260] Formula 202-1(1)

[0261]

[0262] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202A, but the embodiments of the present disclosure are not limited thereto:

[0263] Formula 202A

[0264]

[0265] In one or more embodiments, the compound represented by Formula 202 may be represented by the following Formula 202A-1, but the embodiments of the present disclosure are not limited thereto:

[0266] Formula 202A-1

[0267]

[0268] In equation 201-1, equation 201-2, equation 201-2(1), equation 201A, equation 201A(1), equation 201A-1, equation 202-1, equation 202-1(1), equation 202A, and equation 202A-1,

[0269] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,

[0270] L 205 can be selected from phenylene and fluorenylene,

[0271] X 211 Can be selected from O, S and N (R 211 ),

[0272] X 212 Can be selected from O, S and N (R 212 ),

[0273] R 211 and R 212 can be independently combined with R 203 are defined identically, and

[0274] 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.

[0275] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT48, but the embodiments of the present disclosure are not limited thereto:

[0276]

[0277]

[0278]

[0279]

[0280] The thickness of the hole transport region can be approximately To about In the range of, for example, about To about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in the range of about To about In the range of, for example, about To about In the range of To about In the range of, 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, suitable or satisfactory hole transport characteristics may be obtained without significantly increasing the driving voltage.

[0281] The emission assisting 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 electrons from flowing from the electron transport region. The emission assisting layer and the electron blocking layer can include materials as described herein above.

[0282] p-dopant

[0283] 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.

[0284] The charge generating material may be, for example, a p-dopant.

[0285] In one embodiment, the p-dopant may have a LUMO level of approximately -3.5 eV or less.

[0286] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but embodiments of the present disclosure are not limited thereto.

[0287] In one embodiment, the p-dopant may include at least one selected from the following compounds:

[0288] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0289] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0290] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0291] A compound represented by the following formula 221,

[0292] However, the embodiments of the present disclosure are not limited thereto:

[0293]

[0294] Formula 221

[0295]

[0296] In formula 221,

[0297] R 221 To R 223 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 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:

[0298] Emission layer in the organic layer 150

[0299] 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, or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from 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 one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0300] 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.

[0301] In the emission layer, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0302] The thickness of the emitter layer can be approximately To about In the range of, for example, about To about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without significantly increasing the driving voltage.

[0303] Subject in the emission layer

[0304] In one or more embodiments, the host may include a compound represented by Formula 301 below.

[0305] Formula 301

[0306] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0307] In formula 301,

[0308] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0309] xb11 can be 0, 1, 2, or 3.

[0310] L 301 Can be 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,

[0311] xb1 can be an integer from 0 to 5.

[0312] 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 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 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 ),

[0313] xb21 can be an integer from 1 to 5, and

[0314] Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0315] In one embodiment, Ar in Formula 301 301 Can be selected from:

[0316] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, phenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and

[0317] 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

[0318] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0319] When xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.

[0320] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2 below:

[0321] Formula 301-1

[0322]

[0323] Formula 301-2

[0324]

[0325] In Formula 301-1 and Formula 301-2,

[0326] A 301 To A 304 can be independently selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a benzo[9,10]phenanthrene ring, a pyrene ring, ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spirobifluorene ring, a benzofluorene ring, a dibenzofluorene ring, an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a benzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a benzonaphthothiophene ring and a dinaphthothiophene ring,

[0327] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0328] 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 ),

[0329] xb22 and xb23 can each independently be 0, 1 or 2,

[0330] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,

[0331] L 302 To L 304 can be independently combined with L 301 Same as described,

[0332] xb2 to xb4 may each independently be the same as described in conjunction with xb1, and

[0333] R 302 To R 304 can be independently combined with R 301 Same as described.

[0334] For example, L in Formula 301, Formula 301-1, and Formula 301-2 301 To L 304 Can be independently selected from:

[0335] 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

[0336] 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, 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 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

[0337] Q 31 To Q 33 Same as described here above.

[0338] In one embodiment, R in Formula 301, Formula 301-1, and Formula 301-2 301 To R 304 Can be independently selected from:

[0339] 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

[0340] 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 )(Q32 )、-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

[0341] Q 31 To Q 33 Same as described here above.

[0342] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.

[0343] 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, but embodiments of the present disclosure are not limited thereto:

[0344]

[0345]

[0346]

[0347] The phosphorescent dopant included in the emission layer in the organic layer 150

[0348] The phosphorescent dopant may include an organic metal compound represented by Formula 1.

[0349] The phosphorescent dopant may include an organic metal complex represented by the following Formula 401:

[0350] Formula 401

[0351] M(L 401 ) xc1 (L 402 ) xc2

[0352] Formula 402

[0353]

[0354] In equations 401 and 402,

[0355] 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),

[0356] L 401 can be selected from the ligand represented by formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 can be the same or different from each other,

[0357] L 402 may be an organic ligand, and xc2 may be an integer from 0 to 4, wherein when xc2 is 2 or greater, two or more L 402 can be the same or different from each other,

[0358] X 401 To X 404 may each independently be nitrogen or carbon,

[0359] 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,

[0360] A 401 and A 402 can be independently selected from C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,

[0361] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C(Q 411 )-*', where Q 411 and Q 412 It can be hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,

[0362] X 406 Can be a single bond, O or S,

[0363] 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 C 1 -C 20 Heteroaryl,

[0364] xc11 and xc12 may each independently be an integer from 0 to 10, and

[0365] The * and *' in formula 402 both represent the binding site with M in formula 401.

[0366] In one 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.

[0367] In one or more embodiments, in Formula 402, i) X 401 Can be nitrogen, X 402 It can be carbon, or ii) X 401 and X 402 Both can be nitrogen at the same time.

[0368] In one or more embodiments, R in equation 402 401 and R 402 Can be independently selected from:

[0369] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;

[0370] 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;

[0371] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;

[0372] 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

[0373] -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

[0374] Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, and naphthyl, but the embodiments of the present disclosure are not limited thereto.

[0375] In one or more embodiments, in Formula 401, when xc1 is 2 or greater, two or more L401 Two A's 401 It can be optionally connected via X as a linker 407 Connect, or two or more L 401 Two A's 402 It can be optionally connected via X as a linker 408 Connection (see Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408 can be independently 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), but the embodiments of the present disclosure are not limited thereto.

[0376] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402 It can be selected from halogen, diketone (e.g., acetylacetone), carboxylic acid (e.g., picolinic acid), -C(=O), isonitrile, -CN and phosphorus (e.g., phosphine or phosphite), but the embodiments of the present disclosure are not limited thereto.

[0377] In one or more embodiments, the phosphorescent dopant may be selected from, for example, compound PD1 to compound PD25, but the embodiments of the present disclosure are not limited thereto:

[0378]

[0379]

[0380] Fluorescent dopants in the emitting layer

[0381] The fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0382] The fluorescent dopant may include a compound represented by the following Formula 501:

[0383] Formula 501

[0384]

[0385] In formula 501,

[0386] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0387] L 501 To L 503 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,

[0388] xd1 to xd3 may each independently be an integer from 0 to 3,

[0389] 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

[0390] xd4 can be an integer from 1 to 6.

[0391] In one embodiment, Ar in Formula 501 501 Can be selected from:

[0392] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and

[0393] 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 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,

[0394] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:

[0395] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...

[0396] 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, 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.

[0397] In one or more embodiments, R in Formula 501 501 and R 502 Can be independently selected from:

[0398] 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

[0399] 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

[0400] 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.

[0401] In one or more embodiments, xd4 in equation 501 may be 2, but the embodiments of the present disclosure are not limited thereto.

[0402] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:

[0403]

[0404]

[0405]

[0406] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:

[0407]

[0408] Electron transport region in organic layer 150

[0409] 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.

[0410] 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, but the embodiments of the present disclosure are not limited thereto.

[0411] For example, 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 sequentially stacked from the emission layer in the order stated. However, embodiments of the structure of the electron transport region are not limited thereto.

[0412] 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.

[0413] "π-electron-poor nitrogen-containing ring" means a C-containing ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.

[0414] For example, the "π-electron-poor nitrogen-containing ring" may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion 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=*' portion is condensed with at least one C 5 -C 60 A carbocyclic condensed heteropolycyclic group.

[0415] Examples of π-electron-poor nitrogen-containing rings include, but are not limited to, 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.

[0416] For example, the electron transport region may include a compound represented by Formula 601:

[0417] Formula 601

[0418] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0419] In formula 601,

[0420] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0421] xe11 can be 0, 1, 2, or 3,

[0422] L 601 Can be 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,

[0423] xe1 can be an integer from 0 to 5,

[0424] R 601 Can be 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, 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 ),

[0425] Q 601 To Q 603 can be independently C1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0426] xe21 can be an integer from 1 to 5.

[0427] In one embodiment, xe11 number of Ar 601 and xe21 number of R 601 At least one of the may include a π-electron-poor nitrogen-containing ring.

[0428] In one embodiment, Ar in Formula 601 601 Can be selected from:

[0429] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, phenanthrenyl, phenanthrenyl, phenanthrenyl, phenanthryl, phenanthroline, phenazinyl, phenanthryl ...

[0430] 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

[0431] 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.

[0432] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.

[0433] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.

[0434] In one or more embodiments, the compound represented by Formula 601 may be represented by the following Formula 601-1:

[0435] Formula 601-1

[0436]

[0437] In formula 601-1,

[0438] 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 ), where, from X 614 To X 616 At least one of the selected ones may be N,

[0439] L 611 To L 613 can be independently combined with L 601 Same as described,

[0440] xe611 to xe613 can all be independently defined the same as xe1,

[0441] R 611 To R 613 can be independently combined with R 601 Same as described, and

[0442] 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.

[0443] In one embodiment, L in equation 601 601 and L in formula 601-1 611 To L 613 Can be independently selected from:

[0444] 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

[0445] 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,

[0446] However, the embodiments of the present disclosure are not limited thereto.

[0447] In one or more embodiments, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 may each independently be 0, 1, or 2.

[0448] In one or more embodiments, R in Formula 601 601 and R in formula 601-1 611 To R 613 Can be independently selected from:

[0449] 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;

[0450] 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, 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

[0451] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and

[0452] Q 601 and Q 602 Same as described here above.

[0453] The electron transport region may include at least one compound selected from compound ET1 to compound ET36, but the embodiments of the present disclosure are not limited thereto:

[0454]

[0455]

[0456]

[0457]

[0458] In one or more 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:

[0459]

[0460] The thickness of the buffer layer, the hole blocking layer and the electron control layer can all be about To about In the range of, for example, about To about When the thickness of the buffer layer, the hole blocking layer, and the electron control layer is within these ranges, the buffer layer, the hole blocking layer, and the electron control layer may have excellent hole blocking properties or electron control properties without significantly increasing the driving voltage.

[0461] The thickness of the electron transport layer can be about To about In the range of, for example, about To about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have suitable or satisfactory electron transport characteristics without significantly increasing the driving voltage.

[0462] In addition to the materials described herein above, the electron transport region (eg, an electron transport layer in the electron transport region) may also include a metal-containing material.

[0463] 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 ions, Na ions, K ions, Rb ions, and Cs ions, and the alkaline earth metal complex may include a metal ion selected from Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. 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, but the embodiments of the present disclosure are not limited thereto.

[0464] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or compound ET-D2.

[0465]

[0466] 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.

[0467] The electron injection layer 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.

[0468] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0469] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0470] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0471] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0472] 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.

[0473] 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 one embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0474] 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-x O (0 < x < 1)). In one embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0475] 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 one embodiment, the rare earth metal compound may be selected from YbF3 ScF 3 , TbF 3 ,YbI 3 ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.

[0476] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include ions of alkali metal, alkaline earth metal and rare earth metal as described herein above, and the ligand coordinated to the metal ion of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0477] The electron injection layer can be composed of alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above (or can include alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above). In one or more embodiments, the electron injection layer can also include organic material. When the electron injection layer also includes organic material, alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in the matrix including the organic material.

[0478] The thickness of the electron injection layer can be about To about In the range of, for example, about To about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have suitable or satisfactory electron injection characteristics without significantly increasing a driving voltage.

[0479] The second electrode 190

[0480] The second electrode 190 may be located 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 selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0481] 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, but the embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0482] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0483] Figures 2 to 4 Description

[0484] Figure 2 2 is a schematic diagram of an organic light emitting device 20 according to an embodiment. 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 of this statement. Figure 3 is a schematic diagram of an organic light emitting device 30 according to an embodiment. The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the order of this statement. Figure 4 is a schematic diagram of an organic light emitting device 40 according to an embodiment. 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 order of this statement.

[0485] 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 .

[0486] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer may pass through the first electrode 110 and the first cover layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer may pass through the second electrode 190 and the second cover layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.

[0487] The first capping layer 210 and the second capping layer 220 may improve external light emitting efficiency according to the principle of constructive interference.

[0488] 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.

[0489] 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 optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.

[0490] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0491] In one or more embodiments, at least one selected from the first cap layer 210 and the second cap layer 220 may each independently include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but the embodiments of the present disclosure are not limited thereto:

[0492]

[0493] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the embodiment is described, but the embodiments of the present disclosure are not limited thereto.

[0494] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a set or specific area 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.

[0495] 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 Up to about 10 -3 Torr vacuum and approx. To about The vacuum deposition was performed at a deposition rate of .

[0496] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2000 rpm to about 5000 rpm and at a heat treatment temperature of about 80°C to about 200°C by taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.

[0497] General definitions of at least some of the substituents

[0498] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, 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 The alkyl group has a divalent group having substantially the same structure.

[0499] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, examples of which include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to C 2 -C 60 An alkenyl group is a divalent group having substantially the same structure.

[0500] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 Alkyl refers to a hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., in the middle) or at the end (e.g., terminal), examples of which include ethynyl and propynyl. As used herein, the term “C 2 -C 60 "Alkynylidene" refers to C 2 -C 60 Alkynyl groups are divalent groups having substantially the same structure.

[0501] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (Among them, A 101C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, examples of which include a methoxy group, an ethoxy group and an isopropoxy group.

[0502] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0503] As used herein, the term "C 1 -C 10 The term "heterocycloalkyl" as used herein refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring atoms and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has a divalent group having substantially the same structure.

[0504] 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 not having aromaticity (e.g., not aromatic), 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 is a divalent group having substantially the same structure.

[0505] 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 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.

[0506] 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 (eg, bonded together).

[0507] 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 at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system having at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 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 group includes two or more rings, the rings may be condensed with each other (eg, bonded together).

[0508] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (Among them, A 102 C 6 -C 60 Aryl), as used herein, 6 -C 60 "Arylthio" refers to -SA 103 (Among them, A103 C 6 -C 60 aryl).

[0509] As used herein, the term "monovalent non-aromatic condensed polycyclic group" refers to a monovalent group having two or more rings condensed to each other (e.g., bound together), having only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and containing at least one non-aromatic ring in its entire molecular structure. An 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 substantially the same structure as a monovalent non-aromatic condensed polycyclic group.

[0510] 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 (e.g., bound together), at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms other than carbon atoms (e.g., having 1 to 60 carbon atoms), and containing at least one non-aromatic ring in its entire molecular structure. An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0511] 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. As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to aromatic carbocyclic group or non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more embodiments, the carbonyl group is connected to the carbonyl group. 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.

[0512] 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 having substantially the same structure.

[0513] In this specification, substituted C5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 1 -C 20 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:

[0514] 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;

[0515] 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;

[0516] 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;

[0517] 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 -C60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and

[0518] -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

[0519] 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 groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.

[0520] The term "Ph" as used herein refers to phenyl, the term "Me" as used herein refers to methyl, the term "Et" as used herein refers to ethyl, the term "ter-Bu" or "Bu" as used herein refers to ethyl. t ” means tert-butyl, and the term “OMe” as used herein means methoxy.

[0521] As used herein, the term "biphenyl" refers to a "phenyl group substituted with a phenyl group". 6 -C 60 "substituted phenyl" having "aryl" as a substituent.

[0522] As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group. 6 -C 60 Aryl C 6 -C 60 "substituted phenyl" having "aryl" as a substituent.

[0523] Unless otherwise defined, *, *' and *" as used herein all refer to binding sites to adjacent atoms in the corresponding formula.

[0524] Hereinafter, the compound according to the embodiment and the organic light emitting device according to the embodiment will be described in more detail with reference to the synthesis examples and examples. The expression "using B instead of A" used in describing the synthesis examples means replacing a molar equivalent of A with the same amount of molar equivalent of B.

[0525] Synthesis Example

[0526] Synthesis Example 1: Synthesis of Compound 1

[0527]

[0528] (1) Synthesis of intermediate [1-A]

[0529] 3,5-Dibromobenzonitrile (1.0 eq), imidazole (3.0 eq), CuI (0.02 eq), K 2 CO 3 (3.0eq) and L-proline (0.04eq) were dissolved in dimethyl sulfonate (0.1M) and stirred at 160°C for 48 hours. The reaction mixture was cooled to room temperature, and an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried and concentrated using magnesium sulfate, and purified by column chromatography to synthesize intermediate [1-A] (yield: 42%).

[0530] (2) Synthesis of intermediate [1-B]

[0531] Intermediate [1-A] (1.0 eq) and iodomethane (3.0 eq) were dissolved in toluene (1.0 M) and stirred at 120° C. for 12 hours. The reaction mixture was cooled to room temperature, washed with toluene, and filtered to obtain a solid. The obtained solid was dried to synthesize intermediate [1-B] (yield: 68%).

[0532] (3) Synthesis of intermediate [1-C]

[0533] 2,6-dibromopyridine (1.0 eq), 9H-carbazole-3,6-dicarbonitrile (1.1 eq), CuI (0.01 eq), K 2 CO 3 (2.0 eq) and L-proline (0.02 eq) were dissolved in dimethyl sulfonate (0.1 M) and stirred at 160° C. for 48 hours. The reaction mixture was cooled to room temperature, and an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried and concentrated using magnesium sulfate, and purified by column chromatography to synthesize intermediate [1-C] (yield: 57%).

[0534] (4) Synthesis of intermediate [1-D]

[0535] The reaction solution including methyl 4,4,4-trifluoroacetoacetate (1.0 eq) and acetic acid (1.1 eq) was stirred at a temperature of 6°C, and hydrazine hydrate (1.1 eq) was slowly added thereto for 0.3 hours. The reaction mixture was slowly heated to a temperature of 80°C for 1 hour and stirred for 3 hours. After the reaction was considered complete, the reaction product was cooled to obtain the intermediate [1-D] in the form of crystals (yield: 82%).

[0536] (5) Synthesis of intermediate [1-E]

[0537] Intermediate [1-C] (1.0 eq), intermediate [1-D] (1.2 eq), CuI (0.01 eq), K 2 CO 3 (2.0 eq) and L-proline (0.02 eq) were dissolved in dimethyl sulfonate (0.1 M) and stirred at 160° C. for 48 hours. The reaction mixture was cooled to room temperature, and an organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried and concentrated using magnesium sulfate, and purified by column chromatography to synthesize intermediate [1-E] (yield: 47%).

[0538] (6) Synthesis of Compound 1

[0539] Intermediate [1-B] (1.0 eq), intermediate [1-E] (1.0 eq), iridium chloride hydrate (1.1 eq) and K 2 CO 3(10eq) was dissolved in propionic acid (0.2M) and stirred at a temperature of 140°C for 12 hours. The reaction mixture was cooled to room temperature and the solvent was removed therefrom under reduced pressure. Then, the organic layer was extracted therefrom three times using dichloromethane and water. The extracted organic layer was dried and concentrated using magnesium sulfate and purified by column chromatography to synthesize compound 1 (yield: 22%).

[0540] Synthesis Example 2: Synthesis of Compound 13

[0541]

[0542] (1) Synthesis of intermediate [13-A]

[0543] Intermediate [13-A] was synthesized in substantially the same manner as Intermediate [1-A] except that 3,5-dibromotrifluorotoluene was used instead of 3,5-dibromobenzonitrile (yield: 52%).

[0544] (2) Synthesis of intermediate [13-B]

[0545] Intermediate [13-B] was synthesized in substantially the same manner as Intermediate [1-B] except that Intermediate [13-A] was used instead of Intermediate [1-A] (yield: 80%).

[0546] (3) Synthesis of intermediate [13-C]

[0547] Intermediate [13-C] was synthesized in substantially the same manner as Intermediate [1-C] except that 3,6-bis(trifluoromethyl)-9H-carbazole was used instead of 9H-carbazole-3,6-dicarbonitrile (yield: 67%).

[0548] (4) Synthesis of intermediate [13-D]

[0549] Intermediate [13-D] was synthesized in substantially the same manner as Intermediate [1-E] except that Intermediate [13-C] was used instead of Intermediate [1-C] (yield: 76%).

[0550] (5) Synthesis of Compound 13

[0551] Compound 13 was synthesized in substantially the same manner as Compound 1, except that Intermediate [13-B] was used instead of Intermediate [1-B], and Intermediate [13-D] was used instead of Intermediate [1-E] (yield: 26%).

[0552] Synthesis Example 3: Synthesis of Compound 19

[0553]

[0554] (1) Synthesis of intermediate [19-A]

[0555] Intermediate [19-A] was synthesized in substantially the same manner as Intermediate [1-C] except that 2,6-difluoro-3-hydroxypyridine was used instead of 9H-carbazole-3,6-dicarbonitrile (yield: 49%).

[0556] (2) Synthesis of intermediate [19-B]

[0557] Intermediate [19-B] was synthesized in substantially the same manner as Intermediate [1-E] except that Intermediate [19-A] was used instead of Intermediate [1-C] (yield: 72%).

[0558] (3) Synthesis of Compound 19

[0559] Compound 19 was synthesized in substantially the same manner as Compound 1, except that Intermediate [19-B] was used instead of Intermediate [1-E] (yield: 23%).

[0560] Synthesis Example 4: Synthesis of Compound 25

[0561]

[0562] (1) Synthesis of intermediate [25-A]

[0563] 2,6-dibromopyridine (1.0 eq), (2,6-difluoropyridin-3-yl)boronic acid (1.1 eq), Pd(PPh 3 ) 4 (0.002eq) and K 2 CO 3 (1.0 eq) dissolved in tetrahydrofuran / H 2 O (2: 1, 0.1M), and stirred at 70 ° C for 12 hours. The reaction mixture was cooled to room temperature, and the organic layer was extracted three times using dichloromethane and water. The extracted organic layer was dried and concentrated using magnesium sulfate, and purified by column chromatography to synthesize intermediate [25-A] (yield: 68%).

[0564] (2) Synthesis of intermediate [25-B]

[0565] Intermediate [25-B] was synthesized in substantially the same manner as Intermediate [1-E] except that Intermediate [25-A] was used instead of Intermediate [1-C] (yield: 76%).

[0566] (3) Synthesis of Compound 25

[0567] Compound 25 was synthesized in substantially the same manner as Compound 1, except that Intermediate [25-B] was used instead of Intermediate [1-E] (yield: 27%).

[0568] The compounds synthesized according to Synthesis Examples 1 to 4 1 H NMR and LC-MS are shown in Table 1.

[0569] Those of ordinary skill in the art may also readily recognize methods for synthesizing compounds other than those shown in Table 1 by referring to the synthetic mechanisms and source materials described herein above.

[0570] Table 1

[0571]

[0572]

[0573] Evaluation example

[0574] The maximum emission wavelengths (λ max ), and the compounds synthesized according to Synthesis Examples 1 to 4 are obtained by quantum simulation. 3 The results are shown in Table 2. The maximum emission wavelength (λ max ). The density functional theory (DFT) method and the Gaussian program (available from Gaussian Corporation) were used to calculate the 3 MC state energy levels, wherein the structures of each compound were optimized at the B3LYP / 6-31G(d,p) level (eg, using B3LYP hybrid density functional and 6-31G(d,p) basis set).

[0575] Table 2

[0576] <![CDATA[λ max (nm)]]> <![CDATA[ 3 MC state (eV)<!-- 67 --> ]]> Comparative Compound 1 472 0.24 Comparative Compound 2 498 0.15 Comparative Compound 3 502 0.21 Comparative Compound 4 470 0.02 Compound 1 468 0.24 Compound 13 464 0.23 Compound 19 449 0.19 Compound 25 456 0.21

[0577] Comparative Compound 1

[0578]

[0579] Comparative Compound 2

[0580]

[0581] Comparative Compound 3

[0582]

[0583] Comparative Compound 4

[0584]

[0585] Although the present application is not limited to any particular mechanism or theory, it is believed that when the bond between the ligand and the metal center becomes stronger, a triplet state is formed. 3 The energy level of the MC state increases further.

[0586] From the results in Table 2, it can be seen that compared with Comparative Example 4 including a bidentate ligand, Compound 1, Compound 13, Compound 19 and Compound 25 according to one or more embodiments have high 3 MC state energy level.

[0587] Example

[0588] Example 1

[0589] As the anode, Corning 15Ω / cm 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 device. 2-TNATA was vacuum deposited on the ITO glass substrate to form a A hole injection layer having a thickness of 1000 Å was formed, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum deposited on the hole injection layer to form a Compound 1 (dopant) (weight ratio of 10%) and 3,3-di(9H-carbazole-9-yl)biphenyl (mCBP) (host) were co-deposited on the hole transport layer to form a Then, diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1) is vacuum deposited on the emission layer to form a Then, Alq is deposited on the hole blocking layer. 3 To form a An electron transport layer having a thickness of , and an alkali metal halide LiF is deposited on the electron transport layer to form The electron injection layer is formed by vacuum deposition of Al A thickness of is achieved to form a LiF / Al electrode (cathode electrode), thereby completing the manufacture of an organic light-emitting device.

[0590] Example 2 to Example 4

[0591] Organic light emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 3 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 substantially the same manner as in Example 1, except that Comparative Compounds 1 to 4 were respectively used instead of Compound 1 as a dopant in forming the emission layer.

[0594] Comparative Compound 1

[0595]

[0596] Comparative Compound 2

[0597]

[0598] Comparative Compound 3

[0599]

[0600] Comparative Compound 4

[0601]

[0602] By using Keithley SMU 236 and brightness meter PR650 at 50mA / cm 2 The driving voltage, brightness, luminous efficiency and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 4 and Comparative Examples 1 to 4 were measured at a current density of , and the amount of time (half-life) elapsed when the brightness was 50% of the initial brightness was measured. The results are shown in Table 3.

[0603] Table 3

[0604]

[0605] As can be seen from Table 3, the organic light-emitting devices of Examples 1 to 4, in which the compounds according to one or more embodiments are used as dopants for the emission layer, have low driving voltage, high efficiency, and high color purity compared to the organic light-emitting devices of Comparative Examples 1 to 4. In addition, it can be seen that the lifespan is significantly improved compared to the organic light-emitting devices of Comparative Examples 3 and 4.

[0606] When the compound according to one or more embodiments is used for an organic light emitting device, high color purity may be achieved, and excellent effects may be exhibited in terms of driving voltage, efficiency, and lifespan.

[0607] An organic light emitting device including an organic metal compound may have a low driving voltage, high efficiency, and a long lifetime, and facilitates adjustment of emission wavelength, thereby exhibiting high color purity.

[0608] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should be considered as available for other similar features or aspects in other embodiments.

[0609] It will be understood that, although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the spirit and scope of the present disclosure, the first element, component, region, layer or part described above may be named as the second element, component, region, layer or part.

[0610] For ease of explanation, spatially relative terms such as "under", "below", "below", "under", "above", "on", etc. may be used herein to describe the relationship of one element or feature to another element or feature as shown in the figures. It will be understood that the spatially relative terms are intended to include different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, if the device in the figure is turned over, the element described as "below" or "below" or "below" other elements or features will then be positioned as "above" the other elements or features. Therefore, the example terms "below" and "under" can include both above and below orientations. The device can be positioned otherwise (e.g., rotated 90 degrees or at other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.

[0611] It will be understood that when an element or layer is referred to as being “on,” “connected to,” or “coupled to” another element or layer, it can be directly on, directly connected to, or directly coupled to the other element or layer, or one or more intervening elements or layers may be present. Additionally, it will be understood that when an element or layer is referred to as being “between” two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.

[0612] The terms used herein are only for the purpose of describing specific embodiments and are not intended to limit the present disclosure. As used herein, unless the context clearly indicates otherwise, the singular forms "one" and "a (kind / person)" are also intended to include plural forms. It will also be understood that when the terms "comprise", "include" and their variations are used in this specification, the stated features, wholes, effects, operations, elements and / or components are indicated, but the presence or addition of one or more other features, wholes, effects, operations, elements, components and / or their groups are not excluded.

[0613] As used herein, the terms "substantially," "approximately," and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that would be recognized by one of ordinary skill in the art. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure." As used herein, the term "using" and variations thereof may be considered synonymous with the term "utilizing" and variations thereof, respectively. In addition, the term "exemplary" is intended to indicate an example or illustration.

[0614] In addition, any numerical range stated herein is intended to include all subranges of the same numerical precision contained in the stated range. For example, the range "1.0 to 10.0" is intended to include all subranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the stated minimum value 1.0 and the stated maximum value 10.0), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any subrange contained in the scope explicitly stated herein.

[0615] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the claims and their equivalents.

Claims

1. An organic metal compound, the organic metal compound is represented by Formula 1: ML A L B , in, In formula 1, M is iridium, L A is a tridentate ligand represented by Formula 1A, and L B is a tridentate ligand represented by formula 1B-21: Formula 1A Formula 1B-21 Wherein, in Formula 1A, From the formula 1A The group represented by the formula A1-1 is represented by Wherein, in formula A1-1, X 11 C(R 11 ), X 12 C(R 12 ), and X 13 For N, R 11 and R 12 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 10 Alkyl, C1-C substituted with at least one -F 10 Alkyl, C1-C substituted with at least one -Cl 10 Alkyl, C1-C substituted with at least one -Br 10 Alkyl and C1-C 10 alkyl, From the formula 1A The group represented by the formula A2-11 is represented by Wherein, in formula A2-11, Y2 is N, R2 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy, b21 is selected from 1, 2 and 3, From the formula 1A The group represented by formula A3-13 or express, Among them, Y3 is C, X 31 C(R 31 ), X 32 C(R 32 ), X 33 C(R 33 ), X 34 C(R 34 ), X 35 C(R 35 ), X 36 C(R 36 ), and X 37 C(R 37 ), R3 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, -CF3, -CCl3, -CBr3, -CI3, C1-C 20 Alkyl and C1-C 20 Alkoxy, R 31 , R 33 , R 34 , R 36 and R 37 are independently hydrogen, R 32 and R 35 are independently selected from hydrogen, cyano, methyl, -CF3, -CCl3, -CBr3, -CI3, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, b32 is selected from 1, 2 and 3, In Formula 1B-21, Y5 is C, X 41 C(R 41 ), X 42 C(R 42 ), X 43 C(R 43 ), X 44 C(R 44 ), X 51 C(R 51 ), X 52 C(R 52 ), and X 53 C(R 53 ), R 41 To R 46 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl and C1-C 20 Alkoxy, R 51 To R 53 are independently selected from hydrogen, cyano, methyl, -CF3, -CCl3, -CBr3, -CI3, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, L1 and L2 are independently selected from a direct bond, *-O-*' and *-S-*', n1 is 1, and n2 is 1, * indicates a binding site to M, and *' and *" both indicate a binding site to an adjacent atom.

2. The organometallic compound according to claim 1, wherein R 11 and R 12 At least one of them is cyano or -CF3.

3. The organometallic compound according to claim 2, wherein R 11 is hydrogen, R 12 It is -CF3.

4. The organometallic compound according to claim 3, wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

5. The organometallic compound according to claim 1, wherein The bond between Y1 and M is a covalent bond. The bond between Y2 and M is a coordination bond, and The bond between Y3 and M is a covalent bond.

6. The organometallic compound according to claim 1, wherein i) L1 is selected from *-O-*' and *-S-*', and L2 is a direct bond; or ii) L1 is *-O-*' and L2 is *-O-*', or L1 is *-S-*' and L2 is *-O-*'.

7. The organometallic compound according to claim 1, wherein R3 is selected from hydrogen, -F, -Cl, -Br, -I, cyano, -CF3, -CCl3, -CBr3 and -CI3, and R 32 and R 35 are independently selected from cyano and -CF3.

8. The organometallic compound according to claim 1, wherein R 45 and R 46 are independently selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, and R 41 To R 44 are independently hydrogen.

9. The organometallic compound according to claim 1, wherein R 51 To R 53 Each is independently selected from hydrogen, cyano, -CF3, -CCl3, -CBr3 and -CI3.

10. The organometallic compound according to claim 1, wherein The organometallic compound is selected from the following compounds:

11. 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; as well as At least one of the organometallic compounds according to any one of claims 1 to 10.

12. The organic light emitting device according to claim 11, wherein: The organic layer includes the organic metal compound.

13. The organic light emitting device according to claim 11, wherein: The emission layer includes the organic metal compound.

14. The organic light emitting device according to claim 13, wherein: The emission layer further includes a host, and an amount of the organic metal compound included in the emission layer is in a range of 0.01 parts by weight to 30 parts by weight based on 100 parts by weight of the emission layer.

15. The organic light emitting device according to claim 13, wherein: The emission layer emits light having a maximum emission wavelength of 450 nm or more and 550 nm or less.

16. The organic light emitting device according to claim 11, 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 any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

17. The organic light emitting device according to claim 16, wherein: The hole transport region includes a p-dopant having a lowest unoccupied molecular orbital energy level of -3.5 eV or less.

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