Organometallic compound and organic electroluminescent device containing same
Patent Information
- Application Number
- JP2020189048
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2019-11-28
- Filing Date
- 2020-11-13
- Publication Date
- 2025-01-31
- Estimated Expiration
- 2040-11-13
AI Technical Summary
【0008】 本発明の有機電界発光素子は、高効率及び長寿命を有することができる。
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Abstract
Description
[Technical field]
[0001] The present invention relates to organometallic compounds, organic electroluminescent devices containing same, and devices containing same. [Background technology]
[0002] An organic light emitting device is a self-emitting device that has advantages such as a wide viewing angle, excellent contrast, a short response time, excellent brightness, driving voltage and response speed characteristics, and the ability to be multi-colored.
[0003] An organic electroluminescent device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, a light emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes injected from the first electrode move to the light emitting layer via the hole transport region, and electrons injected from the second electrode move to the light emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. Light is generated when the excitons change from an excited state to a ground state. [Prior art documents] [Patent documents]
[0004] [Patent Document 1] US Patent Application Publication No. 2019 / 0088889 Summary of the Invention [Problem to be solved by the invention]
[0005] The problem to be solved by the present invention is to provide an organometallic compound, an organic electroluminescent device containing the same, and a device containing the same. [Means for solving the problem]
[0006] According to one embodiment of the present invention, there is provided an organometallic compound represented by the following Chemical Formula 1: M(L a ) n1 (L b ) n2 ...(chemical formula 1) (In the above Chemical Formula 1, M is selected from the group consisting of first transition metals, second transition metals, third transition metals and fourth transition metals; L a is selected from ligands represented by the following chemical formula 2: [ka] ...(chemical formula 2) n1 is 1 or 2; L b is selected from monodentate, bidentate and tridentate ligands; n2 is 0, 1, 2, or 3; when n2 is 2 or more, L b are either identical or different, L a and L b are different from each other, In the above Chemical Formula 2, A 1 and A 2 are independent of each other, C 5 -C 30 Carbocyclic groups and C 1 -C 30 heterocyclic groups, X 1 , X 2 , X 3 , X 4 are, independently of each other, C or N, Y 1 and Y 2 are, independently of each other, C or N, T 1 , T 2 and T 3are each independently a single bond, *-O-*', *-S-*', *-C(R 4 )(B 5 )-*', *-Si(R 4 )(R 5 )-*', *-B(R 4 )-*', *-N(R 4 )-*' and *-P(R 4 )-*', R 1 ~R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 2 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 1 )(Q 2 )(Q 3 ), -N(Q 1 )(Q2 ), -B(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 )(Q 2 ), b1 to b3 are each independently an integer of 1, 2, or 3; R 1 ~R 3 Optionally, adjacent groups and each other are connected to a single bond, -C(Q 4 )(Q 5 )-, -Si(Q 4 )(Q 5 )-, -O-, -S-, -N(Q 4 )-, -B(Q 4 )-, C(=O)-, -S(=O) 2 -, -S(=O)(Q 4 )(Q 5 )- and P(=O)(Q 4 )- and substituted or unsubstituted C 5 -C 30 Carbocyclic group or substituted or unsubstituted C 1 -C 30 forming a heterocyclic group or not bonding, a1 and a2 are each independently an integer selected from 0 to 10; a3 is 0, 1 or 2; The above substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 2-C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 2 -C 10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 2 -C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, 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 ) replaced with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups and terphenylyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenylyl group, terphenylyl 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 ) replaced with at least one selected from 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups and terphenylyl groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ); The aforementioned Q 1 ~Q 5 , Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Alkyl-substituted C 6 -C 60 Aryl group, C 1 -C 60 is selected from the group consisting of heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups, and terphenylyl groups; * 1. * 2 and * 3 is a bonding position with the central metal M of Chemical Formula 1, * and *' respectively indicate the bond positions to adjacent atoms.
[0007] According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer including a light-emitting layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the organometallic compound described above. Effect of the Invention
[0008] The organic electroluminescent device of the present invention can have high efficiency and long life. [Brief description of the drawings]
[0009] [Figure 1] 1 is a schematic diagram illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention. [Diagram 2] 2 is a schematic diagram illustrating a structure of an organic electroluminescent device according to another embodiment of the present invention. [Diagram 3] 1 is a schematic diagram illustrating a structure of an organic electroluminescent device according to yet another embodiment of the present invention. [Figure 4] 1 is a schematic diagram illustrating a structure of an organic electroluminescent device according to yet another embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0010] The present invention can be modified in various ways and can have various embodiments, but specific embodiments are illustrated in the drawings and will be described in detail by detailed description. The effects, features, and methods of achieving the present invention will become clear by referring to the embodiments described in detail below together with the drawings. However, the present invention is not limited to the embodiments disclosed below, but can be realized in various forms.
[0011] Hereinafter, an embodiment of the present invention will be described in detail with reference to the accompanying drawings. When describing with reference to the drawings, the same or corresponding elements are designated by the same reference numerals, and duplicated description thereof will be omitted.
[0012] In the following embodiments, the singular expression includes the plural expression unless otherwise clearly indicated in the context.
[0013] In the following embodiments, the terms "comprise" or "have" mean the presence of features or components described in the specification, and do not preclude the possibility that one or more other features or components may be added.
[0014] In the following embodiments, when a part such as a film, region, or component is said to be on or above another part, this does not only mean that it is directly on top of the other part, but also means that there is another film, region, component, etc. in between.
[0015] In the drawings, the size of components may be exaggerated or reduced for the convenience of explanation. For example, the size and thickness of each component shown in the drawings are arbitrarily shown for the convenience of explanation, and the present invention is not necessarily limited to what is shown in the drawings.
[0016] In the present specification, the term "organic layer" refers to any single and / or multiple layers interposed between a first electrode and a second electrode in an organic electroluminescent device. The material contained in the "organic layer" is not limited to organic materials.
[0017] [General definition of substituents] In this specification, C 1 -C 60 The alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. 1 -C 60 The alkylene group is C 1 -C 60 It means a divalent group having the same structure as an alkyl group.
[0018] In this specification, C 2 -C 60 The alkenyl group is the C 2 -C 60 It means a hydrocarbon group containing one or more carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group. 2 -C 60 The alkenylene group is C 2 -C 60 It means a divalent group having the same structure as an alkenyl group.
[0019] In this specification, C 2 -C 60 The alkynyl group is the C 2 -C 60 It means a hydrocarbon group containing one or more carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like. 2 -C 60 The alkynylene group is C 2 -C 60 It means a divalent group having the same structure as an alkynyl group.
[0020] In this specification, C 1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is the aforementioned C 1 -C 60 Specific examples of the aryl group include methoxy, ethoxy, and isopropyloxy groups.
[0021] In this specification, C 3 -C 10 Cycloalkyl groups are C 3 -C 10 It means a monovalent saturated hydrocarbon monocyclic group, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like. 3 -C 10 The cycloalkylene group is C3 -C 10 It means a divalent group having the same structure as a cycloalkyl group.
[0022] In this specification, C 1 -C 10 The heterocycloalkyl group is a C alkyl group containing at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. 1 -C 10 Specific examples of the cyclic ring include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. 1 -C 10 The heterocycloalkylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group.
[0023] In this specification, C 3 -C 10 The cycloalkenyl group is C 3 -C 10 It means a monovalent monocyclic group having at least one double bond in the ring but not having aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 3 -C 10 The cycloalkenylene group is C 3 -C 10 It means a divalent group having the same structure as a cycloalkenyl group.
[0024] In this specification, C 1 -C 10 The heterocycloalkenyl group is a C alkyl group containing at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. 1 -C 10 It is a monovalent monocyclic group having at least one double bond in the ring. 1 -C 10Specific examples of the heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. 1 -C 10 The heterocycloalkenylene group is C 1 -C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.
[0025] In this specification, C 6 -C 60 The aryl group is C 6 -C 60 means a monovalent radical having a carbocyclic aromatic system, C 6 -C 60 The arylene group is C 6 -C 60 C means a divalent group having a carbocyclic aromatic system. 6 -C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. 6 -C 60 Aryl groups and C 6 -C 60 When an arylene group contains two or more rings, the two or more rings may be fused together. 7 -C 60 The alkylaryl group is a group having at least one C 1 -C 60 Alkyl-substituted C 6 -C 60 It means an aryl group.
[0026] In this specification, C 1 -C 60 The heteroaryl group is a heteroaryl group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom. 1 -C 60 means a monovalent group having a heterocyclic aromatic system, C 1 -C 60The heteroarylene group contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 -C 60 It means a divalent group having a heterocyclic aromatic system. 1 -C 60 Specific examples of the heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene group contains two or more rings, the two or more rings may be fused together. 2 -C 60 The alkylheteroaryl group is a heteroaryl group having at least one C 1 -C 60 Alkyl-substituted C 1 -C 60 It means a heteroaryl group.
[0027] In this specification, C 6 -C 60 The aryloxy group is -OA. 102 (Here, A 102 is the aforementioned C 6 -C 60 aryl group), C 6 -C 60 The arylthio group is -SA 103 (Here, A 103 is the aforementioned C 6 -C 60 aryl group).
[0028] In this specification, C 1 -C 60 The heteroaryloxy group is -OA. 104 (Here, A 104 is the aforementioned C 1 -C 60 Heteroaryl group), C 1 -C 60 The heteroarylthio group is -SA 105 (Here, A105 is the aforementioned C 1 -C 60 A heteroaryl group is shown.
[0029] In the present specification, the term "non-aromatic condensed polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed with each other, the ring atoms are only carbon atoms, and the entire molecule has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. In the present specification, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having the same structure as the above-mentioned monovalent non-aromatic condensed polycyclic group.
[0030] In the present specification, the term "non-aromatic condensed heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed with each other and which contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom other than carbon, and the entire molecule has non-aromaticity. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. In the present specification, the term "divalent non-aromatic condensed heteropolycyclic group" refers to a divalent group having the same structure as the above-mentioned monovalent non-aromatic condensed heteropolycyclic group.
[0031] In this specification, C 5 -C 60 A carbocyclic group refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms and containing only carbon as ring-forming atoms. 5 -C 60 A carbocyclic group is an aromatic or non-aromatic carbocyclic group. 5 -C 60 A carbocyclic group is a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. 5 -C 60 Depending on the number of substituents attached to the carbocyclic group, 5 -C 60The carbocyclic group can be variously modified, such as being a trivalent or tetravalent group.
[0032] In this specification, C 1 -C 60 The heterocyclic group is the aforementioned C 5 -C 60 It has the same structure as a carbocyclic group, but contains at least one heteroatom selected from N, O, Si, P, and S in addition to carbon (which may have 1 to 60 carbon atoms) as ring-forming atoms.
[0033] As used herein, the aforementioned substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene groups, substituted C 3 -C 10 Cycloalkenylene groups, substituted C 1 -C 10 Heterocycloalkenylene groups, substituted C 6 -C 60 Arylene Groups, Substituted C 1 -C 60 Heteroarylene groups, substituted divalent nonaromatic condensed polycyclic groups, substituted divalent nonaromatic condensed heteropolycyclic groups, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 1 -C10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 7 -C 60 Alkylaryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 Heteroaryl Groups, Substituted C 2 -C 60 Alkylheteroaryl groups, substituted C 1 -C 60 Heteroaryloxy groups, substituted C 1 -C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 Alkylheteroaryl groups, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 Heteroarylthio group, 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 ) replaced with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 Alkylheteroaryl groups, C1 -C 60 Heteroaryloxy group, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 Alkylheteroaryl groups, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 Heteroarylthio group, 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 ) replaced with at least one selected from 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 Alkylheteroaryl groups, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 Heteroarylthio groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ); The aforementioned Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1-C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 Alkylheteroaryl groups, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 C substituted with at least one selected from the group consisting of a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, deuterium, -F, and a cyano group 1 -C 60 C substituted with at least one selected from the group consisting of an alkyl group, a deuterium, -F, and a cyano group 6 -C 60 It is selected from the group consisting of aryl, biphenylyl and terphenylyl groups.
[0034] As used herein, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "But" means a tert-butyl group, and "OMe" means a methoxy group.
[0035] In the present specification, the term "biphenylyl group" means a "phenyl group substituted with a phenyl group." A "biphenylyl group" is a group in which the substituent is "C 6 -C 60It belongs to the "substituted phenyl group" which is an "aryl group."
[0036] In the present specification, the term "terphenylyl group" means a "phenyl group substituted with a biphenylyl group". 6 -C 60 Aryl-substituted C 6 -C 60 It belongs to the "substituted phenyl group" which is an "aryl group."
[0037] In this specification, unless otherwise defined, * and *' refer to the bond positions to adjacent atoms in the chemical formula.
[0038] [Organometallic compound] The organometallic compound of the present disclosure is represented by the following chemical formula 1: M(L a ) n1 (L b ) n2 ...(chemical formula 1)
[0039] In Formula 1, M is selected from the group consisting of first transition metals, second transition metals, third transition metals, and fourth transition metals.
[0040] According to one example, M is selected from the group consisting of, but not limited to, platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), iridium (Ir), rhodium (Rh), cobalt (Co), meitnerium (Mt), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).
[0041] For example, M is selected from the group consisting of iridium (Ir), cobalt (Co), rhodium (Rh) and meitnerium (Mt).
[0042] In Chemical Formula 1, n1 can be 1 or 2.
[0043] In Chemical Formula 1, L a is selected from ligands represented by the following chemical formula 2. [ka] ...(chemical formula 2)
[0044] The details of Chemical Formula 2 will be described later.
[0045] In Chemical Formula 1, L b is selected from monodentate, bidentate and tridentate ligands, n2 is 0, 1, 2 or 3, and when n2 is 2 or more, 2 or more L b may be the same or different. b The specific details of this will be described later.
[0046] In Chemical Formula 1, L a and L b may be different from each other.
[0047] According to one example, in Formula 1, M is selected from the group consisting of iridium (Ir), cobalt (Co), rhodium (Rh) and meitnerium (Mt); n1 is 1; and n2 is 1, 2 or 3.
[0048] For example, 9M is iridium (Ir), n1 is 1, and n2 is 1.
[0049] In Chemical Formula 2, A 1 and A 2 are independent of each other, C 5 -C 30 Carbocyclic groups and C 1 -C 30 The heterocyclic group is selected from the group consisting of aryl, ... and heterocyclic groups.
[0050] According to one example, A 1 and A 2 are independent of each other, i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings and one or more second rings are fused to each other, the first ring may have a ring structure selected from cyclopentane, cyclopentene, cyclopentadiene, furan, thiophene, pyrrole, borole, phosphole, silole, germole, selenophene, oxazole, dihydrooxazole, isoxazole, dihydroisoxazole, oxadiazole, dihydrooxadiazole, isoxadiazole, dihydroisoxadiazole, oxatriazole, dihydrooxatriazole, isoxatriazole, dihydroisoxatriazole, thiazole, dihydrothiazole, isothiazole, dihydroisothiazole, thiadiazole, dihydrothiadiazole, isothiadiazole, dihydroisothiadiazole, thiatriazole, dihydrothiatriazole, isothiazole, dihydroisothiatriazole, pyrazole, dihydropyrazole, imidazole, dihydroimidazole, triazole, dihydrotriazole, tetrazole, dihydrotetrazole, azasilole, diazasirol, and triazasirol, The second ring may have a ring structure selected from the group consisting of cyclohexane, cyclohexene, cyclohexadiene, adamantane, norbornane, norbornene, benzene, pyridine, dihydropyridine, tetrahydropyridine, pyrimidine, dihydropyrimidine, tetrahydropyrimidine, pyrazine, dihydropyrazine, tetrahydropyrazine, pyridazine, dihydropyridazine, tetrahydropyridazine, and triazine, but is not limited thereto.
[0051] According to another example, A 1 and A 2are each independently selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, furan, thiophene, silole, indene, fluorene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilole, dibenzosilole, indole, carbazole, indenopyridine, indolopyridine, benzofuropyridine, benzothienopyridine, benzosilolopyridine, indenopyrimidine, indolopyrimidine, benzofuropyrimidine, benzothienopyrimidine, benzosilolopyrimidine, pyridine, pyrimidine, pyrimidine, The ring structure may be selected from the group consisting of aryl, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, imidazopyridine, imidazopyrimidine, imidazopyrazine, benzoxazole, benzothiazole, benzoxadiazole, and benzothiadiazole, but is not limited thereto.
[0052] According to yet another example, A 1 and A 2 may each independently have a ring structure selected from benzene, naphthalene, indene, fluorene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilole, dibenzosilole, indole, carbazole, indenopyridine, indolopyridine, benzofuropyridine, benzothienopyridine, benzosilolopyridine, indenopyrimidine, indolopyrimidine, benzofuropyrimidine, benzothienopyrimidine, benzosilolopyrimidine, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, benzopyrazole, benzimidazole, imidazopyridine, imidazopyrimidine, imidazopyrazine, benzoxazole, benzothiazole, benzoxadiazole, and benzothiadiazole, but are not limited thereto.
[0053] In Chemical Formula 2, X 1 , X 2 , X 3 , X 4 are, independently of each other, C or N.
[0054] According to one example, (i) X 1 is C and X 2 is C and X 3 is C and X 4 is C, or (ii) X 1 is N and X 2 is C and X 3 is C and X 4 is C or (iii) X 1 is C and X 2 is N and X 3 is C and X 4 is C, or (iv) X 1 is C and X 2 is C and X 3 is N and X 4 is C or (v) X 1 is C and X 2 is C and X 3 is C and X 4 is N, or (vi) X 1 is N and X 2 is N and X 3 is C and X 4 is C or (vii) X 1 is N and X 2 is C and X 3 is N and X 4 is C or (viii) X 1 is N and X 2 is C and X 3 is C and X 4 is N or (ix) X 1 is C and X 2 is N and X 3 is N and X 4 is C or (x)X 1 is C and X 2is N and X 3 is C and X 4 is N or (xi) X 1 is C and X 2 is C and X 3 is N and X 4 is N or (xii) X 1 is N and X 2 is N and X 3 is N and X 4 is C or (xiii) X 1 is N and X 2 is N and X 3 is C and X 4 is N or (xiv) X 1 is N and X 2 is C and X 3 is N and X 4 is N or (xv)X 1 is N and X 2 is N and X 3 is N and X 4 is N or (xvi) X 1 is C and X 2 is N and X 3 is N and X 4 is N.
[0055] In Chemical Formula 2, Y 1 and Y 2 are, independently of each other, C or N.
[0056] For example, (i) Y 1 is C and Y 2 is C, or (ii) Y 1 is C and Y 2 is N, or (iii) Y 1 is N and Y 2 is C or (iv) Y 1 is N and Y 2 is N.
[0057] In Chemical Formula 2, T 1 , T 2and T 3 are each independently a single bond, *-O-*', *-S-*', *-C(R 4 )(R 5 )-*', *-Si(R 4 )(R 5 )-*', *-B(R 4 )-*', *-N(R 4 )-*' and *-P(R 4 )-*' is selected.
[0058] According to one example, T 1 , T 2 and T 3 is a single bond.
[0059] According to another example, T 1 , T 2 and T 3 At least one of the following is *-O-*', *-S-*', *-C(R 4 )(R 5 )-*', *-Si(R 4 )(R 5 )-*', *-B(R 4 )-*', *-N(R 4 )-*' and *-P(R 4 )-*' is selected.
[0060] According to yet another example, T 1 and T 2 At least one of the following is *-O-*', *-S-*', *-C(R 4 )(B 5 )-*', *-Si(R 4 )(R 5 )-*', *-B(R 4 )-*', *-N(R 4 )-*' and *-P(R 4 )-*', and T 3 is a single bond.
[0061] For example, T 1 and T 3 is a single bond, T 2 *-O-*', *-S-*', *-C(R 4 )(B5 )-*', *-Si(R 4 )(R 5 )-*', *-B(R 4 )-*', *-N(R 4 )-*' and *-P(R 4 )-*' is selected.
[0062] Another example is T 1 and T 3 is a single bond, T 2 is *-O-*'.
[0063] In Chemical Formula 2, b1 to b3 are each independently an integer of 1, 2, or 3.
[0064] According to one example, the above b1 to b3 are 1.
[0065] In Chemical Formula 2, R 1 ~R 5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 2 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -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 ) is selected.
[0066] For example, the aforementioned R 1 ~R 5 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenylyl, terphenylyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentacenyl, pyrroly a phenyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanyl group, anthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof phenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; Deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group , a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof azaphenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group, indolocarbazolyl group, -C(Q 31 )(Q 32 )(Q 33)、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of Perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group , cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzo azothiophenyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl groups; and -C(Q1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q2) and -P(=S)(Q 1 )(Q 2 ); Q 1 ~Q 3 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C1 -C 60 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 Alkyl group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 The aryl group may be selected from, but is not limited to, heteroaryl groups.
[0067] According to another example, the aforementioned R 1 ~R 5 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; and C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 alkoxy groups; but are not limited to these.
[0068] For example, the above mentioned R 1 ~R 5 are independent of each other, Hydrogen, deuterium, -F, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl; and The alkyl group may be selected from, but is not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl groups substituted with at least one selected from deuterium, -F, and a cyano group.
[0069] In Chemical Formula 2, the above-mentioned R 1 ~R 3 Optionally, adjacent groups and each other are connected to a single bond, -C(Q 4 )(Q 5 )-, -Si(Q 4 )(Q 5 )-, -O-, -S-, -N(Q 4 )-, -B(Q 4 )-, C(=O)-, -S(=O) 2 -, -S(=O)(Q 4 )(Q 5 )- and P(=O)(Q 4 )-bonded, substituted or unsubstituted C 5 -C 30 Carbocyclic group or substituted or unsubstituted C 1 -C 30 A heterocyclic group can be formed.
[0070] In Chemical Formula 2, a1 and a2 are each independently an integer selected from 0 to 10.
[0071] In Chemical Formula 2, a3 is 0, 1 or 2.
[0072] According to one example, Chemical Formula 2 may be represented by the following Chemical Formula 2-1 or Chemical Formula 2-2. [ka] ...(chemical formula 2-1) [ka] ...(Chemical formula 2-2)
[0073] In Chemical Formula 2-1 and Chemical Formula 2-2, A 1 , A 2 , R 1 , R 2 , a1, a2, X 3 , X 4 , Y 1 , Y 2 , T 1 , T 2 , T 3 , b1, b2, b3, * 1. * 2 and * 3. Refer to the above and R 31 , R 32 , R 33 , R 34 , R 35 and R 36 Each of them is the aforementioned R 3 Please refer to the description below.
[0074] According to one example, in Formula 1, L b is a tridentate ligand and n2 may be 1.
[0075] According to one example, L b may be selected from ligands represented by the following formula 3: [ka] ...(chemical formula 3)
[0076] In Chemical Formula 3, A 11 is C 5 -C 30 Carbocyclic groups and C 1 -C 30 heterocyclic groups, L 1 and L 2 are each independently a single bond, *-O-*', *-S-*', *-C(R 14 )(R 15 )-*', *-Si(R 14 )(R 15 )-*', *-B(R 14 )-*', *-N(R 14)-*' and *-P(R 14 )-*', c1 and c2 are each independently 1, 2 or 3; X 11 , X 12 , X 13 and X 14 are, independently of each other, C or N, Y 11 is C or N, T 11 , T 12 and T 13 are each independently a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*', *-Si(R 16 )(R 17 )-*', *-B(R 16 )-*', *-N(R 16 )-*' and *-P(R 16 )-*', b11, b12 and b13 are each independently 1, 2 or 3; R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C10 Cycloalkenyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 2 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -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 ), The aforementioned R 11 ~R 13 may be selectively connected to adjacent groups by a single bond, -C(Q 4 )(Q 5 )-, -Si(Q 4 )(Q 5 )-, -O-, -S-, -N(Q 4 )-, -B(Q 4 )-, C(=O)-, -S(=O) 2 -, -S(=O)(Q 4 )(Q 5 )- and P(=O)(Q 4 )- and substituted or unsubstituted C 5 -C 30 Carbocyclic group or substituted or unsubstituted C 1 -C 30 can form a heterocyclic group, a11 is an integer selected from 0 to 10, a12 and a13 are each independently 0, 1, 2 or 3; The above substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 2 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 2 -C 10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 2 -C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, 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 ) replaced with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups and terphenylyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenylyl group, terphenylyl 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 ) replaced with at least one selected from 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups and terphenylyl groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q31)(Q 32 ); The aforementioned Q 1 ~Q 5 , Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60Aryl group, C 1 -C 60 Alkyl-substituted C 6 -C 60 Aryl group, C 1 -C 60 is selected from the group consisting of heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups, and terphenylyl groups; * 1. * 2 and * 3 is a bonding position with the central metal M of Chemical Formula 1, * and *' respectively indicate the bond positions to adjacent atoms.
[0077] According to one example, in formula 3, A 11 are benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, furan, thiophene, silole, indene, fluorene, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, benzosilole, dibenzosilole, indole, carbazole, indenopyridine, indolopyridine, benzofuropyridine, benzothienopyridine, benzosilolopyridine, indenopyrimidine, indolopyrimidine, benzofuropyrimidine, benzothienopyrimidine, benzosilolopyrimidine, pyridine, pyridine The ring structure is selected from the group consisting of imidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, phthalazine, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, imidazopyridine, imidazopyrimidine, imidazopyrazine, benzoxazole, benzothiazole, benzoxadiazole, and benzothiadiazole.
[0078] According to another example, A 11has a ring structure selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, indene, and fluorene, but is not limited thereto.
[0079] According to one example, in formula 3, L 1 and L 2 are all single bonds, but are not limited thereto.
[0080] According to one example, (i) X 11 is C and X 12 is C and X 13 is C and X 14 is C, or (ii) X 11 is N and X 12 is C and X 13 is C and X 14 is C or (iii) X 11 is C and X 12 is N and X 13 is C and X 14 is C, or (iv) X 11 is C and X 12 is C and X 13 is N and X 14 is C or (v) X 11 is C and X 12 is C and X 13 is C and X 14 is N, or (vi) X 11 is N and X 12 is N and X 13 is C and X 14 is C or (vii) X 11 is N and X 12 is C and X 13 is N and X 14 is C or (viii) X 11 is N and X 12 is C and X 13 is C and X 14 is N or (ix) X 11 is C and X12 is N and X 13 is N and X 14 is C or (x)X 11 is C and X 12 is N and X 13 is C and X 14 is N or (xi) X 11 is C and X 12 is C and X 13 is N and X 14 is N or (xii) X 11 is N and X 12 is N and X 13 is N and X 14 is C or (xiii) X 11 is N and X 12 is N and X 13 is C and X 14 is N or (xiv) X 11 is N and X 12 is C and X 13 is N and X 14 is N or (xv)X 11 is N and X 12 is N and X 13 is N and X 14 is N, or (xvi) X 11 is C and X 12 is N and X 13 is N and X 14 is N.
[0081] According to one example, in formula 3, Y 11 is C.
[0082] According to one example, the aforementioned T 11 , T 12 and T 13 are each independently a single bond.
[0083] For example, the aforementioned R 11 , R 12 , R 13 , R 14 , R 15, R 16 and R 17 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenylyl, terphenylyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentacenyl, pyrroly a phenyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanyl group, anthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof phenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; Deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group , a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof azaphenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group, indolocarbazolyl group, -C(Q 31 )(Q 32 )(Q 33)、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of Perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group , cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzo azothiophenyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl groups; and -C(Q1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ); Q 1 ~Q 3 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C 60 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 Alkyl group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 The aryl group may be selected from, but is not limited to, heteroaryl groups.
[0084] According to another example, the aforementioned R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; and C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 alkoxy groups; but are not limited to these.
[0085] According to yet another example, the aforementioned R 11 , R 12 , R 13 , R 14, R 15 , R 16 and R 17 are independent of each other, Hydrogen, deuterium, -F, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl; and The alkyl group may be selected from, but is not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl groups substituted with at least one selected from deuterium, -F, and a cyano group.
[0086] For example, the aforementioned R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 At least one of the groups is selected from the group consisting of -F, a cyano group, and C substituted with at least one of -F and a cyano group. 1 -C 20 The alkyl group is selected from the group consisting of aryl, aryl groups, and alkyl groups.
[0087] For example, the above mentioned R 11 , R 12 and R 13 At least one of the groups is selected from the group consisting of -F, a cyano group, and C substituted with at least one of -F and a cyano group. 1 -C 20 The alkyl group is selected from the group consisting of aryl, aryl groups, and alkyl groups.
[0088] For example, R 13 is -F, a cyano group, or C substituted with at least one of -F and a cyano group; 1 -C 20 The alkyl group is selected from the group consisting of aryl, aryl groups, and alkyl groups.
[0089] According to one example, Formula 3 is an organometallic compound represented by any one of Formulas 3-1 and 3-2 below. [ka] ...(chemical formula 3-1) [ka] ...(chemical formula 3-2)
[0090] In the above-mentioned Chemical Formula 3-1 and Chemical Formula 3-2, A 11 , L 1 , L 2 , c1, c2, Y 11 , T 11 , T 12 , T 13 , b11, b12, b13, R 11 , R 14 , R 15 , R 16 , R 17 , a11, see above, R 12a , R 12b , R 12c , R 12d , R 12e , R 12f and R 12g Each of them is the aforementioned R 12 Please refer to the description of R 13a , R 13b , R 13c , R 13d , R 13e , R 13f and R 13g Each of them is the aforementioned R 13 Please refer to the description below.
[0091] According to one example, the organometallic compound represented by Chemical Formula 1 may be selected from the following Compounds BD1 to BD48. [ka] [ka] [ka] [ka]
[0092] The organometallic compound of the present disclosure contains Ir or the like as M, and therefore has a wide energy difference between the organometallic compounds. a and L b This ligand provides relatively high metal-to-ligand charge transfer (MLCT) and at the same time high spin orbit coupling (SOC) effect (~5,000 cm -1 ), the rate of energy exchange (intersystem crossing) between singlet and triplet can be increased. As a result, the organometallic compound of the present disclosure has a maximum emission wavelength (λ ) of about 390 nm to about 500 nm. max ) can emit phosphorescence with high efficiency.
[0093] The organometallic compounds of the present disclosure include a tridentate ligand L a In the above, the central ring and the adjacent ring are directly bonded to suppress vibration in the excited state, resulting in a high quantum yield (QY).
[0094] The organometallic compound of the present disclosure has a pentagonal heterocycle containing two or more nitrogen atoms as the central ring in the tridentate ligand La, and thus has an improved metal-centered triplet state (3MC state) and structural stability due to the stronger bonding force between the metal and the carbon atom compared to a ligand having a hexagonal heterocycle, for example, pyridine.
[0095] The organometallic compounds of the present disclosure include a tridentate ligand L a By including this ligand, the bonding strength between the ligand and the metal is strengthened, and high structural stability is achieved, as compared with the case where a bidentate ligand is included.
[0096] Those skilled in the art will be able to recognize how to synthesize the organometallic compound represented by Chemical Formula 1 by referring to the Examples below.
[0097] In this specification, "(the organic layer) contains one or more organometallic compounds" is interpreted as "(the organic layer) may contain one organometallic compound belonging to the category of Chemical Formula 1 described above, or two or more different organometallic compounds belonging to the category of Chemical Formula 1 described above."
[0098] For example, the organic layer may contain only the aforementioned compound 1 as the organometallic compound of the present disclosure. In this case, compound 1 may be present in the light-emitting layer of the organic electroluminescent device. Alternatively, the organic layer may contain the aforementioned compound 1 and compound 2 as the organometallic compound of the present disclosure. In this case, 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 light-emitting layer) or may be present in different layers (for example, compound 1 may be present in the light-emitting layer and compound 2 may be present in the electron transport layer).
[0099] The organic layer may include i) a hole transport region interposed between the first electrode (anode) and the light emitting layer, the hole transport region including at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer, and / or ii) an electron transport region interposed between the light emitting layer and the second electrode (cathode), the electron transport region including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. The light emitting layer may include at least one organometallic compound represented by Chemical Formula 1.
[0100] According to one example, the light-emitting layer is a first color light-emitting light-emitting layer, Between the first electrode and the second electrode, i) at least one second color light emitting light emitting layer is additionally included, or ii) at least one second color light emitting light emitting layer and at least one third color light emitting light emitting layer are additionally included, the maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light are the same or different from each other; A mixed-color light in which the first color light and the second color light are mixed together, or a mixed-color light in which the first color light, the first two colors light, and the third color light are mixed together may be emitted.
[0101] The light-emitting layer further includes a host compound. The organometallic compound contained in the light-emitting layer is a dopant, and the content of the host compound in the light-emitting layer is greater than the content of the organometallic compound in the light-emitting layer.
[0102] In this case, the host compound includes a second compound and a third compound, the organometallic compound, the second compound, and the third compound are different from each other, the second compound and the third compound form an exciplex, and the organometallic compound of the present disclosure and the second compound and / or the third compound do not form an exciplex.
[0103] An exciplex is effectively formed between the second compound and the third compound, but an exciplex is not formed between the organometallic compound of the present disclosure and the second compound and / or the third compound, so that the stable host energy (energy of the second compound and / or the third compound) is efficiently transferred to the dopant (the organometallic compound of the present disclosure), thereby improving the efficiency of the organic electroluminescent device. If an exciplex is formed between the organometallic compound and the second compound and / or the third compound, the emission wavelength of the organometallic compound will shift to a longer wavelength due to the formation of the exciplex, and the desired emission from the organometallic compound will not be obtained, thereby reducing the efficiency of the organic electroluminescent device within the desired wavelength range.
[0104] In one example, the second compound may also be represented by the following formula 4-1, and the third compound may be represented by the following formula 4-2. [ka] ...(Chemical formula 4-1) [ka] ...(Chemical formula 4-2)
[0105] In Chemical Formula 4-1 and Chemical Formula 4-2, X21 is C(R 21 ) and N; X 22 is C(R 22 ) and N; X 23 is C(R 23 ) and N; X 24 is C(R 24 ) and N; X 25 is C(R 25 ) and N; X 26 is C(R 26 ) and N; X 21 ~X 26 At least one of is N, R 21 ~R 26 are independent of each other, *-(L 21 ) a21 -(R 27 ) b27 Groups represented by the symbol, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6-C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), but R 21 ~R 26 At least one of the following is *-(L 21 ) a21 -(R 27 ) b27 is a group represented by L 21 is a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 heterocyclic groups, a21 is selected from integers of 0 to 6; R 27 is a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2), b27 is selected from the group consisting of integers from 1 to 10; X 31 is a single bond, O, S, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ) and Si(R 33 )(R 34 ), and X 32 is a single bond, O, S, B(R 35 ), N(R 35 ), C(R 35 )(R 36 ) and Si(R 35 )(R 36 ), and X 31 and X 32 is not a single bond at the same time, Ring A 31 and Ring A 32 are independent of each other, C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, R 31 ~R 36 are independent of each other, *-(L 31 ) a31 -(R 37 ) b37 Groups represented by the formula (I), hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), but R 31 ~R 36 At least one of the following is *-(L 31 ) a31 -(R 37 )b 37 is a group represented by b31 and b32 are each independently selected from integers of 1 to 10; L 31 is a substituted or unsubstituted C5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 heterocyclic groups, a31 is selected from integers of 0 to 6; R 37 is a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), b37 is selected from the group consisting of integers from 1 to 10; Q 1 ~Q 3 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C 60 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60Alkyl group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 heteroaryl groups, * indicates the bond position to the adjacent atom.
[0106] For example, in Chemical Formula 4-1, X 21 ~X 26 At least one of them is N, and at least one of them is C[(L 21 ) a21 -(R 27 )b 27 ], but is not limited to this.
[0107] For example, in Chemical Formula 4-1, X 21 is N and X 22 is C(R 22 ), and X 23 is C(R 23 ), and X 24 is C(R 24 ), and X 25 is C(R 25 ), and X 26 is C(R26) or X 21 is N and X 22 is C(R 22 ), and X 23 is N and X 24 is C(R 24 ), and X 25 is C(R 25 ), and X 26 is C(R 26 ) or X 21 is N and X 22 is C(R 22), and X 23 is C(R 23 ), and X 24 is N and X 25 is C(R 25 ), and X 26 is C(R 26 ) or X 21 is N and X 22 is C(R 22 ), and X 23 is N and X 24 is C(R 24 ), and X 25 is N and X 26 is C(R 26 ), but is not limited to these.
[0108] For example, in formula 4-1, R 21 ~R 26 are independent of each other, *-(L 21 ) a21 -(R 27 ) b27 Groups represented by the formula: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl groups, and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenylyl, terphenylyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentacenyl, pyrroly a phenyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanyl group, anthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof phenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; Deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group , a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof azaphenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group, indolocarbazolyl group, -C(Q 31 )(Q 32 )(Q 33)、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of Perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group , cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzo azothiophenyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl groups; and -C(Q1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), Q 1 ~Q 3 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C 60 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 Alkyl group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 The aryl group may be selected from, but is not limited to, heteroaryl groups.
[0109] As another example, in formula 4-1, R 21 ~R 26 are independent of each other, *-(L 21 ) a21 -(R 27 ) b27 groups represented by the formula: hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, and C 1 -C 20 Alkyl groups; C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I and a cyano group; 1 -C 20 Alkyl groups; Groups represented by the following chemical formulas 5-1 to 5-139; and -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0110] In Chemical Formula 5-1 to Chemical Formula 5-139, X 51 is O, S, N(R 51 ) and C(R 51 )(R 60 ), X 52 is N or C(R 52 ), and X 53 is N or C(R 53 ), and X 54 is N or C(R 54 ), and X 55 is N or C(R 55 ), and X 56 is N or C(R 56 ), and X 57 is N or C(R 57 ), and X 58 is N or C(R 58 ), and X 59 is N or C(R 59 ) and R 51 ~R 60 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, thiophenyl group, furanyl group, silolyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, -C(Q 31 )(Q 32 )(Q 33 ), -Si(Q 31 )(Q 32 )(Q 33 ), -B(Q 31 )(Q 32 ), -N(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O) 2 (Q 31 ), -P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 ), Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, C 1 -C 60 selected from the group consisting of alkyl, phenyl, biphenylyl and terphenylyl groups; b51 is selected from 1, 2, 3, 4 and 5; b52 is selected from 1, 2, 3, 4, 5, 6 and 7; b53 is selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9; b54 is selected from 1, 2, 3 and 4; b55 is selected from 1, 2 and 3; b56 is selected from 1 and 2; b57 is selected from 1, 2, 3, 4, 5 and 6; * indicates the bond position to the adjacent atom.
[0111] For example, in Chemical Formula 4-1, L 21 are a phenylene group, a naphthylene group, a phenalenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a benzoquinoxalinylene group, a quinazolinylene group, a benzoquinazolinylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenylyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, chrysenyl group, fluoranthenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazolyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazolyl group , dinaphthofuranyl group, dinaphthothiophenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazolyl group, a phenylene group, a naphthalenylene group, a phenalenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazire group, a pyridazinylene group, a triphenylene group, ...ene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pyridinylene group, a pyrazire group, a pyridazinylene group, a triphenylene group, a phenylene group, a naphthalenylene group, a phenalenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylene group, a phenylene group, a naphthalenylene group, a phenalenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pyridinylene group, a pyrazire group, a pyridazinylene group, a triphenylene group, a phenylene group, a naphthalenylene group, a naphthalenylene group, an anthracenylene group, a fluoranthenylene group, a fluoranthenylene group, a a azinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a benzoquinoxalinylene group, a quinazolinylene group, a benzoquinazolinylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; but is not limited thereto.
[0112] For example, in Chemical Formula 4-1, a21 is selected from integers of 0 to 2, but is not limited thereto.
[0113] For example, in formula 4-1, R 27 is hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenylyl, terphenylyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentacenyl, pyrroly a phenyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanyl group, anthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof phenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; Deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group , a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof azaphenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group, indolocarbazolyl group, -C(Q 31 )(Q 32 )(Q 33)、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 )及び-P(=S)(Q 31 )(Q 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of Perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group , cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzo azothiophenyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl groups; and -C(Q1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q1), -S(=O) 2 (Q 1 ), -P(=O)(Q1)(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), Q 1 ~Q 3 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C60 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 Alkyl group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 The aryl group may be selected from, but is not limited to, heteroaryl groups.
[0114] As another example, in formula 4-1, R 27 is hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl groups; C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and a cyano group 1 -C 20 Alkyl groups; Groups represented by Chemical Formulae 5-1 to 5-139; and -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q1)(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2); Q 1 ~Q 3 are independent of each other, C 1 -C 60 It is selected from the group consisting of alkyl, phenyl, biphenylyl and terphenylyl groups, but is not limited thereto.
[0115] As yet another example, in Formula 4-1, R 27 is -C(Q 1 )(Q 2 )(Q 3 ) and -Si(Q 1 )(Q 2 )(Q 3 );and It is selected from the group represented by the following chemical formula 7-1 and the group represented by the following chemical formula 7-2, but is not limited thereto. [ka] ...(chemical formula 7-1) [ka] ...(chemical formula 7-2)
[0116] In Chemical Formula 7-1 and Chemical Formula 7-2, Y 71 is a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 1 -C 60Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31 )(Q 32 )(Q 33 ), and -Si(Q 31 )(Q 32 )(Q 33 ), Ring A 71 is C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, X 71 is C(R 71 ) and N; R 71 and R 72 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6-C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31 )(Q 32 )(Q 33 ), -Si(Q 31 )(Q 32 )(Q 33 ), -B(Q 31 )(Q 32 ), -N(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O) 2 (Q 31 ), -P(=O)(Q 31 )(Q 32 ), and -P(=S)(Q 31 )(Q 32 ), R 71 and R 72 Two groups selected from the group consisting of 5 -C 30 Carbocyclic group or substituted or unsubstituted C 1 -C 30 may form a heterocyclic group, b72 is selected from the group consisting of integers from 1 to 10; Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 heteroaryl groups, * indicates the bond position to the adjacent atom.
[0117] For example, in Chemical Formula 7-1 and Chemical Formula 7-2, ring A 71 For an explanation of 11 Please refer to the explanation about.
[0118] For example, in Chemical Formula 4-2, X 31 is a single bond, O, S, B(R 33 ), N(R 33 ), C(R 33 )(R 34 ) and Si(R 33 )(R 34 ), X 32 is O, S, B(R 35 ), N(R 35 ), C(R 35 )(R 36 ) and Si(R 35 )(R 36 ), but is not limited to these.
[0119] As another example, in the chemical formula 4-2, X 31 is a single bond, O, S, N(R 33), C(R 33 )(R 34 ) and Si(R 33 )(R 34 ), X 32 is O, S, N(R 35 ), C(R 35 )(R 36 ) and Si(R 35 )(R 36 ), but is not limited to these.
[0120] For example, in formula 4-2, ring A 31 and Ring A 32 are, independently of one another, cyclohexane, cyclohexene, cyclohexadiene, benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, silyne, oxacillin, thiacilyne, azacyline, disilyne, dioxin, oxathiin, oxazine, dithiin, thiazine, fluorene, carbazole, dibenzofuran, dibenzothiophene, benzofluorene, benzocarbazole, benzonaphthofuran, benzonaphthothiophene, indolofluorene, indolocarbazole, indolodibenzofuran, indolodibenzothiophene, indenofluorene, and the like. The ring structure may be selected from the group consisting of, but is not limited to, diphenylene, indenocarbazole, indenodibenzofuran, indenodibenzothiophene, benzofuranofluorene, benzofuranocarbazole, benzofuranodibenzofuran, benzofuranodibenzothiophene, benzothienofluorene, benzothienocarbazole, benzothienodibenzofuran, benzothienodibenzothiophene, dibenzosiline, dibenzoxasiline, dibenzothiasiline, dibenzoazasiline, dibenzodisiline, dibenzodioxin, dibenzoxathiin, dibenzoxazine, dibenzodithiin, and dibenzothiazine.
[0121] For example, in formula 4-2, R 31 ~R 36 are independent of each other, *-(L 31 )a31 -(R 37 ) b37 Groups represented by the formula: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl groups, and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenylyl, terphenylyl, pentalenyl, indenyl, naphthyl, azulenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentacenyl, pyrroly a phenyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanyl group, anthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof phenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; Deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group , a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof azaphenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group, indolocarbazolyl group, -C(Q 31 )(Q 32 )(Q 33)、-Si(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 3 1)、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 )及び-P(=S)(Q 31 )(Q 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of Perylenyl group, pentacenyl group, pyrrolyl group, thiophenyl group, furanyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphtho benzothiophenyl, naphthobenzosilolyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthosilolyl, imidazopyridinyl, imidazopyrimidinyl, oxazolopyridinyl, thiazolopyridinyl, benzonaphthyridinyl, azafluorenyl, azaspiro-bifluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilolyl, indenopyrrolyl, indolopyrrolyl, indenocarbazolyl and indolocarbazolyl groups; Groups represented by the following chemical formulas 8-1 and 8-2; and -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q2), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q1), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but is not limited to: [ka] ...(chemical formula 8-1) [ka] ...(chemical formula 8-2)
[0122] In Chemical Formula 8-1 and Chemical Formula 8-2, X 81 is N, C(R 83 ) and Si(R 83 ), X 82 is a single bond, O, S, B(R 84 ), N(R 84 ), C(R 84 )(R 85 ) and Si(R 84 )(R 85 ), X 83 is a single bond, O, S, B(R 86 ), N(R 86 ), C(R 86 )(R 87 ) and Si(R 86 )(R 87), In Chemical Formula 8-2, X 82 and X 83 is not a single bond at the same time, Ring A 81 and Ring A 82 are independent of each other, C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, R 81 ~R 87 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentacenyl group , a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzosilolyl group, benzothiazolyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiof azaphenyl group, naphthobenzosilolyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilolyl group, imidazopyridinyl group, imidazopyrimidinyl group, oxazolopyridinyl group, thiazolopyridinyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilolyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group, indolocarbazolyl group, -C(Q 31 )(Q 32 )(Q 33), -Si(Q 31 )(Q 32 )(Q 33 ), -B(Q 31 )(Q 32 ), -N(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O) 2 (Q 31 ), -P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 ), b81 and b82 are each independently selected from integers of 1 to 10; * indicates the bond position to the adjacent atom, Q 1 ~Q 3 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C 60 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 Alkyl group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C 60 The heteroaryl group is selected from the group consisting of aryl, ... and heteroaryl groups.
[0123] As another example, in formula 4-2, R 31 ~R 36 are independent of each other, *-(L 31 ) a31 -(R 37 ) b37 groups represented by the formula: hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, and C 1 -C 20 Alkyl groups; C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, and a cyano group 1 -C 20 Alkyl groups; Groups represented by chemical formulas 5-1 to 5-139; Groups represented by chemical formula 8-1 and chemical formula 8-2; and -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1)(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ); Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, C 1 -C 60 It is selected from the group consisting of alkyl, phenyl, biphenylyl and terphenylyl groups, but is not limited thereto.
[0124] For example, in formula 4-2, L 31 are a phenylene group, a naphthylene group, a phenalenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a benzoquinoxalinylene group, a quinazolinylene group, a benzoquinazolinylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, phenanthrenyl group, triphenylenyl group, chrysenyl group, fluoranthenyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzofluorenyl group, benzocarbazolyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, dibenzofluorenyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinolinyl group, isoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, azafluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, diazafluorenyl group, diazacarbazolyl group,
[0043] The substituents may be selected from the group consisting of a phenylene group, a naphthylene group, a phenalenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pyridinylene group, a pyrimidinylene group, a pyrazylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a benzoisoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a benzoquinoxalinylene group, a quinazolylene group, a benzoquinazolylene group, a fluorenylene group, a carbazolylene group, a dibenzofuranylene group, and a dibenzothiophenylene group, but are not limited thereto.
[0125] For example, in Chemical Formula 4-2, a31 is selected from integers of 0 to 2.
[0126] For example, in formula 4-2, R 37 is selected from the group represented by Chemical Formula 8-1 and the group represented by Chemical Formula 8-2.
[0127] For example, in Chemical Formula 8-1 and Chemical Formula 8-2, ring A 81 and Ring A82 are, independently of one another, cyclohexane, cyclohexene, cyclohexadiene, benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, sarin, oxacillin, thiaciline, azacyline, disilyline, dioxin, oxathiin, oxazine, dithiin, thiazine, fluorene, carbazole, dibenzofuran, dibenzothiophene, benzofluorene, benzocarbazole, benzonaphthofuran, benzonaphthothiophene, indolofluorene, indolocarbazole, indolodibenzofuran, indolodibenzothiophene In some embodiments, the ring structure is selected from the group consisting of benzothienofluorene, indenocarbazole, indenodibenzofuran, indenodibenzothiophene, benzofuranofluorene, benzofuranocarbazole, benzofuranodibenzofuran, benzofuranodibenzothiophene, benzothienofluorene, benzothienocarbazole, benzothienodibenzofuran, benzothienodibenzothiophene, dibenzosiline, dibenzoxasiline, dibenzothiasiline, dibenzoazasiline, dibenzodisiline, dibenzodioxin, dibenzoxathiin, dibenzoxazine, dibenzodithiin, and dibenzothiazine.
[0128] In one example, the second compound may be represented by any one of the following formulas 4-1-1 and 4-1-2, but is not limited thereto. [ka] ...(Chemical formula 4-1-1) [ka] ...(Chemical formula 4-1-2)
[0129] In Chemical Formula 4-1-1 and Chemical Formula 4-1-2, X 21 is C(R 21 ) and N; X 23 is C(R 23 ) and N; X24 is C(R 24 ) and N; X 25 is C(R 25 ) and N; X 26 is C(R 26 ) and N; In the chemical formula 4-1-1, X 21 , and X 23 ~X 26 At least one of is N, In Chemical Formula 4-1-2, X 21 , and X 23 ~X 25 At least one of is N, R 21 , and R 23 ~R 26 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 ), -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), L 21a and L 21b are each independently a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 heterocyclic groups, a21a and a21b are each independently selected from an integer of 0 to 6; R 27a and R 27b are independent of each other, -C(Q 1 )(Q 2 )(Q 3 ) and -Si(Q 1 )(Q 2 )(Q 3 );and Selected from a group represented by the following chemical formula 7-1 and a group represented by the following chemical formula 7-2: [ka] ...(chemical formula 7-1) [ka] ...(chemical formula 7-2)
[0130] In Chemical Formula 7-1 and Chemical Formula 7-2, Y 71 is a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31 )(Q 32 )(Q 33 ), and -Si(Q 31 )(Q 32 )(Q 33 ), Ring A 71 is C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, X 71 is C(R 71 ) and N; R 71 and R 72are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 31 )(Q 32 )(Q 33 ), -Si(Q 31 )(Q 32 )(Q 33 ), -B(Q 31 )(Q 32 ), -N(Q 31 )(Q 32 ), -P(Q 31 )(Q 32), -C(=O)(Q 31 ), -S(=O)(Q 31 ), -S(=O) 2 (Q 31 ), -P(=O)(Q 31 )(Q 32 ), and -P(=S)(Q 31 )(Q 32 ), R 71 and R 72 Two groups selected from the group consisting of 5 -C 30 Carbocyclic group or substituted or unsubstituted C 1 -C 30 may form a heterocyclic group, b72 is selected from the group consisting of integers from 1 to 10; b27a and b27b are each independently selected from an integer of 1 to 10; Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic group, deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 6 -C 60 Aryl group, and deuterium · -F · cyano group · C 1 -C 10 C substituted with at least one selected from the group consisting of alkyl, phenyl and biphenylyl groups 1 -C60 heteroaryl groups, * indicates the bond position to the adjacent atom.
[0131] In one example, the second compound is selected from Group II below, and the third compound is selected from Group III below, but is not limited thereto. <Group II> [ka] [ka] [ka] [ka] [ka] <Group III> [ka] [ka]
[0132] In the time-resolved electroluminescence (TREL) spectrum of the organic light-emitting element, the decay time of delayed fluorescence is 50 ns or more, for example, 50 ns or more and 10 μs or less. As another example, in the TREL spectrum of the organic light-emitting element, the decay time of delayed fluorescence is 1.4 μs or more and 4 μs or less, or 1.5 μs or more and 3 μs or less. When the decay time of delayed fluorescence of the organic light-emitting element satisfies the above-mentioned range, the time during which the organometallic compound of the present disclosure exists in an excited state is relatively shortened, and the organic light-emitting element can have high luminous efficiency and long life.
[0133] According to one example, the absolute difference between the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound of the present disclosure and the LUMO energy level of the second compound is 0.1 eV or more and 1.0 eV or less, or the absolute difference between the LUMO energy level of the organometallic compound of the present disclosure and the LUMO energy level of the third compound is 0.1 eV or more and 1.0 eV or less, and the absolute difference between the highest occupied molecular orbital (HOMO) energy level of the organometallic compound and the HOMO energy level of the second compound is 1.25 eV or less (e.g., 1.25 eV or less and 0.2 eV or more), or the absolute difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the third compound is 1.25 eV or less (e.g., 1.25 eV or less and 0.2 eV or more).
[0134] By satisfying the above-mentioned relationship between the LUMO energy level and the HOMO energy level, the injection of holes and electrons in the light-emitting layer is balanced.
[0135] [Explanation of Figure 1] 1 is a schematic cross-sectional view of an organic electroluminescent device 10 according to an embodiment of the present invention. The organic electroluminescent device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0136] Hereinafter, a structure and a method for manufacturing an organic electroluminescent device 10 according to an embodiment of the present invention will be described with reference to FIG.
[0137] [First electrode 110] 1, a substrate may be added or disposed below the first electrode 110 or above the second electrode 190. As the substrate, a glass substrate or a plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness may be used.
[0138] The first electrode 110 may be formed by providing a first electrode material on the upper part of a substrate using, for example, a deposition method or a sputtering method. When the first electrode 110 is an anode, the first electrode material is selected from materials having a high work function so as to facilitate hole injection.
[0139] The first electrode 110 is a reflective electrode, a semi-transparent electrode, or a transparent electrode. To form the first electrode 110 as a transparent electrode, the material for the first electrode is selected from the group consisting of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 In order to form the first electrode 110, which is a semi-transmissive electrode or a reflective electrode, the material for the first electrode is selected from, but is not limited to, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof.
[0140] The first electrode 110 may have a single-layer structure, which is a single layer, or a multi-layer structure having multiple layers, for example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.
[0141] [Organic layer 150] An organic layer 150 is provided on the first electrode 110. The organic layer 150 includes a light-emitting layer.
[0142] The organic layer 150 may further include a hole transport region interposed between the first electrode 110 and the light emitting layer, and / or an electron transport region interposed between the light emitting layer and the second electrode 190.
[0143] [Hole transport region in organic layer 150] The hole transport region can have i) a monolayer structure consisting of a single layer of a single material, ii) a monolayer structure consisting of a single layer of multiple different materials, or iii) a multilayer structure having multiple layers consisting of multiple different materials.
[0144] The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, and an electron blocking layer (EBL).
[0145] For example, the hole transport region may have a single layer structure consisting of a plurality of single layers made of different materials, or may have a multi-layer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / light emitting auxiliary layer, a hole injection layer / light emitting auxiliary layer, a hole transport layer / light emitting auxiliary layer, or a hole injection layer / hole transport layer / electron blocking layer, which are stacked in this order from the first electrode 110, but is not limited to these.
[0146] 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″-tris(carbazol-9-yl)-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 the following formula 201, and a compound represented by the following formula 202. [ka] [ka] [ka] ...(chemical formula 201) [ka] ...(chemical formula 202)
[0147] In Chemical Formula 201 and Chemical Formula 202, L 201 ~L 204 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C1 -C 60 is selected from the group consisting of a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic heterocyclic group; L 205 *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene group, substituted or unsubstituted C 2 -C 20 Alkenylene group, substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 is selected from the group consisting of a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic heterocyclic group; xa1 to xa4 are each independently selected from integers of 0 to 3; xa5 is selected from an integer from 1 to 10; R 201 ~R 204 , and Q 201 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 It is selected from the group consisting of a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0148] For example, in formula 202, R 201 and R 202 may be optionally bonded to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, R 203 and R 204 may alternatively be bonded to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.
[0149] According to one embodiment, in formula 201 and formula 202, L 201 ~L 205 are independent of each other, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups, and pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C 1 -C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, -Si(Q 31 )(Q 32 )(Q 33 ), and -N(Q 31 )(Q 32a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, or a naphthacenylene group, each of which is substituted with at least one selected from the group consisting of groups, picenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene groups, rubicenylene groups, coronenylene groups, ovalenylene groups, thiophenylene groups, furanylene groups, carbazolylene groups, indolylene groups, isoindolylene groups, benzofuranylene groups, benzothiophenylene groups, dibenzofuranylene groups, dibenzothiophenylene groups, benzocarbazolylene groups, dibenzocarbazolylene groups, dibenzosilolylene groups and pyridinylene groups; The aforementioned Q 31 ~Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0150] According to another example, xa1 to xa4 are 0, 1 or 2, independently of each other.
[0151] In yet another embodiment, xa5 is 1, 2, 3 or 4.
[0152] According to yet another example, R 201 ~R 204 , and Q 201are each independently a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthalenyl group, phthalocenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C 1 -C 10 Phenyl groups substituted with alkyl groups, phenyl groups substituted with -F, pentalenyl groups, indenyl groups, naphthyl groups, azulenyl groups, heptalenyl groups, indacenyl groups, acenaphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, naphthyl groups, Tacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, -Si(Q31 )(Q 32 )(Q 33 ), and -N(Q 31 )(Q 32 ), substituted with at least one selected from the group consisting of a phenyl group, a biphenylyl group, a terphenylyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a phenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; The aforementioned Q 31 ~Q 33 For the explanation of the above, please refer to the description in this specification.
[0153] According to yet another example, in formula 201, R 201 ~R 203 At least one of, independently of each other, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C 1 -C 10phenyl groups substituted with an alkyl group, phenyl groups substituted with -F, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups substituted with at least one selected from the group consisting of naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups; but are not limited thereto.
[0154] According to yet another example, in formula 202, i) R 201 and R 202 may be bonded to each other via a single bond, and / or ii) R 203 and R 204 may be bonded to each other via a single bond.
[0155] According to yet another example, in formula 202, R 201 ~R 204 At least one of the Carbazolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C 1 -C 10 A phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a carbazolyl group substituted with at least one selected from a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; but is not limited to these.
[0156] The compound represented by formula 201 may be represented by the following formula 201-1: [ka] ...(chemical formula 201-1)
[0157] For example, the compound represented by formula 201 may be represented by, but is not limited to, formula 201-2: [ka] ...(Chemical formula 201-2)
[0158] As yet another example, the compound represented by chemical formula 201 may be represented by the following chemical formula 201-2(1), but is not limited thereto. [ka] ...(Chemical formula 201-2(1))
[0159] The compound represented by formula 201 may be represented by the following formula 201A: [ka] ...(chemical formula 201A)
[0160] For example, the compound represented by chemical formula 201 may also be represented by the following chemical formula 201A(1), but is not limited thereto. [ka] ...(chemical formula 201A(1))
[0161] As yet another example, the compound represented by formula 201 may be represented by the following formula 201A-1, but is not limited thereto. [ka] ...(Chemical formula 201A-1)
[0162] According to one example, the compound represented by formula 202 may be represented by formula 202-1 below: [ka] ...(Chemical formula 202-1)
[0163] According to yet another example, the compound represented by formula 202 may be represented by the following formula 202-1(1): [ka] ...(chemical formula 202-1(1))
[0164] The compound represented by formula 202 may be represented by formula 202A below. [ka] ...(chemical formula 202A)
[0165] According to yet another example, the compound represented by formula 202 may be represented by the following formula 202A-1: [ka] ...(chemical formula 202A-1)
[0166] In the above-mentioned chemical formula 201-1, chemical formula 201-2, chemical formula 201-2(1), chemical formula 201A, chemical formula 201A(1), chemical formula 201A-1, chemical formula 202-1, chemical formula 02-1(1), chemical formula 202A and chemical formula 202A-1, L 201 ~L 203 , xa1 to xa3, xa5, and R 202 ~R 204 For the description of L 205 is selected from the group consisting of a phenylene group and a fluorenylene group; X 211 is O, S and N(R 211 ), X 212 is O, S and N(R 212 ), R 211 and R 212 The explanation for R 203 Please refer to the explanation of R 213 ~R 217 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 Phenyl substituted with an alkyl group, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and pyridinyl group.
[0167] The hole transport region may contain at least one compound selected from the following compounds HT1 to HT48, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0168] The thickness of the hole transport region is about 10 nm to about 1000 nm, for example, about 10 nm to about 100 nm. If the hole transport region includes at least one layer of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 10 nm to about 900 nm, for example, about 10 nm to about 100 nm, and the thickness of the hole transport layer is about 5 nm to about 200 nm, for example, about 10 nm to about 150 nm. When the thicknesses of the hole transport region, hole injection layer, and hole transport layer satisfy the above-mentioned ranges, sufficient hole transport properties can be obtained without a substantial increase in driving voltage.
[0169] The light-emitting auxiliary layer is a layer that compensates for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer to increase light emission efficiency, and the electron blocking layer is a layer that prevents electron injection from the electron transport region. The light-emitting auxiliary layer and the electron blocking layer may contain the material contained in the hole transport region as described above.
[0170] [p-dopant] In addition to the materials described above, the hole transport region may further include a charge generating material to enhance electrical conductivity. The charge generating material may be dispersed uniformly or non-uniformly within the hole transport region.
[0171] The charge generating material can be, for example, a p-dopant.
[0172] According to one example, the LUMO of the p-dopant is less than or equal to -3.5 eV.
[0173] The p-dopant may include at least one selected from the group consisting of quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto.
[0174] For example, p-dopants include quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; 1,4,5,8,9,11-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and The compound represented by the following formula 221 may include at least one selected from the following, but is not limited thereto. <hat-cn>
change
[0175] In formula 221, R 221 ~R 223 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 1 -C 60 is selected from the group consisting of a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, 221 ~R 223 At least one of the C substituted with a cyano group, -F, -Cl, -Br, -I, or -F 1 -C 20 Alkyl group, C substituted with -Cl 1 -C 20 C substituted with alkyl group, -Br 1 -C 20 C substituted with alkyl group and -I 1 -C 20 It has at least one substituent selected from the group consisting of alkyl groups.
[0176] [Light-emitting layer in organic layer 150] When the organic electroluminescent device 10 is a full-color organic electroluminescent device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer for each individual subpixel. Alternatively, the light-emitting layer may have a structure in which two or more layers selected from the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer are stacked in contact with each other or at a distance from each other, or may have a structure in which two or more materials selected from the red light-emitting material, the green light-emitting material, and the blue light-emitting material are mixed without layer division, and may emit white light.
[0177] The light-emitting layer may include a host and a dopant. For the description of the host, refer to the description of the second compound and the third compound, and for the description of the dopant, refer to the description of the organometallic compound represented by Chemical Formula 1 in the present disclosure.
[0178] In the light-emitting layer, the content of the dopant is generally selected from the range of about 0.01 to about 15 parts by weight per about 100 parts by weight of the host, but is not limited thereto.
[0179] The thickness of the light-emitting layer is about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the light-emitting layer satisfies the above-mentioned range, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.
[0180] [Host in the light-emitting layer] The host may include a compound represented by the following formula 301: [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ...(chemical formula 301)
[0181] In the chemical formula 301, Ar 301 is a substituted or unsubstituted C 5 -C 60 Carbocyclic group or substituted or unsubstituted C 1 -C 60 is a heterocyclic group, xb11 is 1, 2 or 3; L 301 is a substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 is selected from the group consisting of a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic heterocyclic group; xb1 is selected from integers from 0 to 5; R 301 is deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl groups, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -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 ), xb21 is selected from integers from 1 to 5; Q 301 ~Q 303 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups, but is not limited thereto.
[0182] According to one example, in formula 301, Ar 301 teeth, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran and dibenzothiophene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran and dibenzothiophene; Q 31 ~Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It may also be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups, but is not limited thereto.
[0183] In the chemical formula 301, when xb11 is 2 or more, 2 or more Ar 301 may be bonded to each other via a single bond.
[0184] According to another example, the compound represented by formula 301 may be represented by the following formula 301-1 or formula 301-2: [ka] ...(chemical formula 301-1) [ka] ...(chemical formula 301-2)
[0185] In Chemical Formula 301-1 and Chemical Formula 301-2, A 301 ~A 304 have a ring structure selected from, independently of one another, benzene, naphthalene, phenanthrene, fluoranthene, triphenylene, pyrene, chrysene, pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene; X 301 is O, S or N-[(L 304 ) xb4 -R 304 ], R 311 ~R 314 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ), xb22 and xb23 are independently 0, 1 or 2; L 301 , xb1, R 301 , and Q 31 ~Q 33 For the description of L 302 ~L 304 The explanations for L 301 Please refer to the explanation of For the explanation of xb2 to xb4, refer to the explanation of xb1 independently. R 302 ~R 304 The explanations for each are independent of each other, R 301 Please refer to the explanation about.
[0186] For example, in formula 301, formula 301-1, and formula 301-2, L 301 ~L 304 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group , isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo -aryl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, or a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; The aforementioned Q 31 ~Q 33 For an explanation of this, please refer to the description in this specification.
[0187] As another example, in formula 301, formula 301-1, and formula 301-2, R 301 ~R 304 are independent of each other, Phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, imidazolyl, pyrazolyl , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazo -aryl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group; The aforementioned Q 31 ~Q 33 For an explanation of this, please refer to the description in this specification.
[0188] As yet another example, the host may include an alkaline earth metal complex, for example, the host may be selected from the group consisting of a Be complex (e.g., compound H55 below), a Mg complex, and a Zn complex.
[0189] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthylene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), 4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), and the following compounds H1 to H124, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0190] The host may also include at least one of a silicon-containing compound (eg, BCPDS, etc.) and a phosphine oxide-containing compound (eg, POPCPA, etc.).
[0191] The host may vary in many ways, such as including only one compound or including two or more compounds that are different from one another (eg, BCPDS and POPCPA).
[0192] [Phosphorescent dopants included in the light-emitting layer of organic layer 150] The light-emitting layer may further include a phosphorescent dopant. The phosphorescent dopant may include an organometallic complex represented by the following formula 401 or 402. M(L 401 ) xc1 (L 402 ) xc2 ...(chemical formula 401) [ka] ...(chemical formula 402)
[0193] In Chemical Formula 401 and Chemical Formula 402, M is selected from the group consisting of iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm); L 401 is selected from the ligands represented by chemical formula 402, xc1 is 1, 2 or 3, and when xc1 is 2 or more, 2 or more L 401 may be the same or different, L 402 is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, 2 or more L 402 may be the same or different, X 401 ~X 404 are, independently of each other, nitrogen or carbon; X 401 and X 403 is bonded through a single or double bond, and X 402 and X 404 is bonded via a single or double bond, A 40 1 and A 402 are independent of each other, C 5 -C 60 Carbocyclic group or C 1 -C 60 is a heterocyclic group, X 405 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C(Q 411 )=*', and the above Q 411 and Q 412 are hydrogen, deuterium, and C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; X 406 is a single bond, O or S, R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 20 Alkyl groups, substituted or unsubstituted C 1 -C 20 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O) 2 (Q 401 ), and -P(=O)(Q 401 )(Q 402 ) and the above Q 401 ~Q 403 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy group, C 6 -C 20 Aryl groups and C 1 -C 20 heteroaryl groups, xc11 and xc12 are each independently selected from an integer of 0 to 10; In chemical formula 402, * and *' are the bonding positions to M in chemical formula 401.
[0194] According to one example, in formula 402, A 401 and A 402 have a ring structure selected from benzene, naphthalene, fluorene, spiro-bifluorene, 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.
[0195] According to another example, in formula 402, i) X 401 is nitrogen, and X 402 is carbon, or ii) X 401 and X 402 Both are nitrogen.
[0196] According to yet another example, in formula 402, R 401 and R 402 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, and a norbornenyl group; 1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 selected from the group consisting of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group cyclopentyl, cyclohexyl, adamantanyl, norbornanyl, norbornenyl, phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl groups, each of which is substituted with at least one of the following: -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 ); The aforementioned Q 401 ~Q 403 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from the group consisting of alkoxy, phenyl, biphenylyl and naphthyl groups, but is not limited thereto.
[0197] According to yet another example, in the chemical formula 401, when xc1 is 2 or more, 2 or more L 401 In this case, two A 401 may optionally be linked to a linking group, X 407 or two A 402 may optionally be linked to a linking group, X 408 (See compounds PD1 to PD4 and compound PD7 below). 407 and X 408 are, independently of each other, 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 are independently hydrogen, deuterium, and C 1 -C 20 Alkyl group, C 1 -C 20 The alkyl group may be, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group.
[0198] In the formula 401, L 402 is any monovalent, divalent or trivalent organic ligand. For example, L 402 is selected from, but is not limited to, halogen, diketone (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), -C(=O), isonitrile, -CN, and phosphoros (e.g., phosphine, phosphite).
[0199] The phosphorescent dopant is selected from, for example, the following compounds PD1 to PD25, but is not limited thereto. [ka] [ka] [ka]
[0200] [Fluorescent dopants included in the light-emitting layer of organic layer 150] The light-emitting layer may further include a fluorescent dopant. The fluorescent dopant may further include an arylamine compound or a styrylamine compound.
[0201] The fluorescent dopant may include a compound represented by formula 501 below: [ka] ...(chemical formula 501)
[0202] In the chemical formula 501, Ar 501 is a substituted or unsubstituted C 5 -C 60 Carbocyclic group or substituted or unsubstituted C 1 -C 60 is a heterocyclic group, L 501 ~L 503 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 is selected from the group consisting of a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic heterocyclic group; xd1 to xd3 are each independently selected from integers of 0 to 3; R 501 and R 502 are each independently a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 is selected from the group consisting of a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic heterocyclic group; xd4 is selected from integers from 1 to 6.
[0203] According to one example, Ar in formula 501 501 teeth, naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, indenoanthracenyl, and indenophenanthrenyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 a naphthyl group, a heptalenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, an indenoanthracenyl group, and an indenophenanthrenyl group, each of which is substituted with at least one selected from an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.
[0204] According to another example, in formula 501, L 501 ~L 503 are independent of each other, phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, thiophenylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilolylene and pyridinylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 substituted with at least one selected from the group consisting of an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group and a pyridinylene group;
[0205] According to yet another example, in formula 501, R 501 and R 502 are independent of each other, phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, phenyl groups, biphenylyl groups, terphenylyl groups, naphthyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, triphenylenyl groups, pyrenyl groups, chrysenyl groups, perylenyl groups, pentaphenyl groups, hexacenyl groups, pentacenyl groups, thiophenyl groups, furanyl groups, carbazolyl groups, indolyl groups, isoindolyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, dibenzosilolyl groups, pyridinyl groups and -Si(Q 31 )(Q 32 )(Q 33 phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups, The aforementioned Q 31 ~Q 33 is C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0206] In yet another example, in chemical formula 501, xd4 is 2, but is not limited to this.
[0207] For example, the fluorescent dopant may be selected from among the following compounds FD1 to FD22. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0208] Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto: [ka] [ka]
[0209] [Electron transport region in organic layer 150] The electron transport region can have i) a monolayer structure consisting of a single layer of a single material, ii) a monolayer structure consisting of a single layer of multiple different materials, or iii) a multilayer structure having multiple layers consisting of multiple different materials.
[0210] The electron transport region may include, but is not limited to, at least one layer selected from a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer (ETL), and an electron injection layer.
[0211] For example, the electron transport region may have a structure, such as, stacked in order from the light emitting layer, an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron modulating layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, but is not limited thereto.
[0212] The electron transport region may include a second compound as described above.
[0213] According to one example, the electron transport region includes a buffer layer, which is in direct contact with the light-emitting layer, and which may include a second compound as described above.
[0214] According to another example, the electron transport region includes a buffer layer, an electron transport layer, and an electron injection layer stacked in this order on the light emitting layer, and the buffer layer may include the second compound as described above.
[0215] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron modulating layer, or an electron transport layer in an electron transport region) may include a non-metal-containing compound that includes at least one π-electron deficient nitrogen-containing ring.
[0216] A "π-electron deficient nitrogen-containing ring" is a ring-forming partial structure having at least one *-N=*' partial structure. 1 -C 60 It means a heterocyclic group.
[0217] For example, the "π-electron deficient nitrogen-containing ring" is i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' partial structure, ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups having at least one *-N=*' partial structure are condensed with each other, or iii) at least one of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' partial structure and at least one C 5 -C 60 A heteropolycyclic group is a group in which a carbocyclic group and a cyclic group are condensed together.
[0218] Specific examples of the π-electron deficient nitrogen-containing ring 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.
[0219] For example, the electron transport region may include a compound represented by formula 601 below. [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ...(chemical formula 601)
[0220] In the chemical formula 601, Ar 601 is a substituted or unsubstituted C 5 -C 60 Carbocyclic group or substituted or unsubstituted C 1 -C 60 is a heterocyclic group, xe11 is 1, 2 or 3, L 601 is a substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene groups, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 is selected from the group consisting of a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic heterocyclic group; xe1 is selected from integers from 0 to 5, R 601 is a substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ), The aforementioned Q 601 ~Q 603 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; xe21 is selected from integers of 1 to 5.
[0221] According to one example, Ar corresponds to the number of xe11 601 , and R corresponding to the number of xe21 601 At least one of the above may contain a π-electron deficient nitrogen-containing ring as described above.
[0222] According to one example, the ring Ar in formula 601 601 teeth, Benzene, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, isopropyl alcohol, ethyl ... a ring structure selected from among thiazole, 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; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ), substituted with at least one selected from the group consisting of benzene, naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, indenoanthracene, dibenzofuran, dibenzothiophene, carbazole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidazole, a ring structure selected from among benzene, 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; The aforementioned Q 31 ~Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It is selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0223] In the chemical formula 601, when xe11 is 2 or more, 2 or more Ar 601 may be bonded to each other via a single bond.
[0224] According to another example, Ar in formula 601 601 may be an anthracene ring.
[0225] According to yet another example, the compound represented by formula 601 is represented by the following formula 601-1: [ka] ...(chemical formula 601-1)
[0226] In the chemical formula 601-1, X 614 is N or C(R 614 ), and X 615 is N or C(R 615 ), and X 616 is N or C(R 616 ), and X 614 Or X 616 At least one of is N, L 611 ~L 613 are independent of each other, L 601 Please refer to the explanation of xe611~xe613 are independent of each other, please refer to the explanation of xe1. R 611 ~R 613 are, independently of each other, R 601 Please refer to the explanation of R 614 ~R 616 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 It is selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0227] According to one example, in formula 601 and formula 601-1, L 601 , and L 611 ~L 613 are independent of each other, Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group , isothiazolylene groups, oxazolylene groups, isoxazolylene groups, thiadiazolylene groups, oxadiazolylene groups, pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, a zolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexaphenylene group, or a phenylene group, each of which is substituted with at least one selected from an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; a cenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group,triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group, but are not limited thereto.
[0228] According to another example, in chemical formula 601 and chemical formula 601-1, xe1 and xe611 to xe613 are 0, 1, or 2, independently of each other.
[0229] According to yet another example, in formula 601 and formula 601-1, R 601 , and R 611 ~R 613 are independent of each other, Phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, pyridinyl, imidazolyl, pyrazolyl a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, a zolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, or a pentaphenyl group, each of which is substituted with at least one selected from an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group,benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl groups; and -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ); The aforementioned Q 601 and Q 602 For the explanation of the above, please refer to the description in this specification.
[0230] The electron transport region may contain at least one compound selected from the following compounds ET1 to ET36, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0231] Alternatively, the electron transport region may be 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, 3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), NTAZ, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1), and 3P-T2T. [ka] [ka]
[0232] The thickness of the buffer layer, the hole blocking layer, or the electron control layer is, independently of each other, about 2 nm to about 100 nm, for example, about 3 nm to about 30 nm. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer satisfies the above-mentioned range, excellent hole blocking properties or electron control properties can be obtained without a substantial increase in driving voltage.
[0233] The thickness of the electron transport layer is about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer satisfies the above-mentioned range, sufficient electron transport properties can be obtained without a substantial increase in driving voltage.
[0234] The electron transport region (eg, an electron transport layer in an electron transport region) may further include a metal-containing material in addition to the materials described above.
[0235] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkali metal complex is selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the metal ion of the alkaline earth metal complex is selected from Be ion, Mg ion, Ca ion, Sr ion, and Ba ion. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex are each independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.
[0236] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate (LiQ)) or ET-D2. [ka]
[0237] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer can be in direct contact with the second electrode 190.
[0238] The electron injection layer can have i) a single layer structure consisting of a single layer made of a single material, ii) a single layer structure consisting of single layers made of a plurality of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials.
[0239] The electron injection layer may comprise 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.
[0240] The alkali metal is selected from the group consisting of Li, Na, K, Rb and Cs. According to one example, the alkali metal is Li, Na or Cs. According to another example, the alkali metal is Li or Cs, but is not limited thereto.
[0241] The alkaline earth metal is selected from the group consisting of Mg, Ca, Sr, and Ba.
[0242] The rare earth metal is selected from the group consisting of Sc, Y, Ce, Tb, Yb and Gd.
[0243] The alkali metal compounds, alkaline earth metal compounds and rare earth metal compounds may be selected from among oxides and halides (e.g., fluorides, chlorides, bromides, iodides, etc.) of alkali metals, alkaline earth metals and rare earth metals.
[0244] Alkali metal compounds include Li 2 O, Cs 2 OK 2 The alkali metal compound may be selected from the group consisting of alkali metal oxides such as LiF, LiO, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, RbI. According to one example, the alkali metal compound is LiF, Li 2 The inorganic oxide may be selected from the group consisting of O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.
[0245] The alkaline earth metal compound may be selected from alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1), Ba x Ca 1-x O(0 < x < 1). According to one example, the alkaline earth metal compound is selected from BaO, SrO, and CaO, but is not limited thereto.
[0246] The rare earth metal compound may be selected from YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , YbI 3 , ScI 3 , TbI 3 and TbF 3 . According to one example, the rare earth metal compound is selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3 , but is not limited thereto.
[0247] The aforementioned alkali metal complex, alkaline earth metal complex, and rare earth metal complex contain the ions of the aforementioned alkali metal, alkaline earth metal, and rare earth metal, and the ligands coordinated to the metal ions of the aforementioned alkali metal complex, alkaline earth metal complex, and rare earth metal complex are, independently of each other, selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.
[0248] The electron injection layer may consist of only the above-mentioned 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, or may further contain an organic substance. When the electron injection layer further contains an organic substance, the above-mentioned 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 is uniformly or non-uniformly dispersed in a matrix made of the organic substance.
[0249] The thickness of the electron injection layer may be about 0.1 nm to about 10 nm, or about 0.3 nm to about 9 nm. When the thickness of the electron injection layer satisfies the above-mentioned range, sufficient electron injection characteristics can be obtained without a substantial increase in driving voltage.
[0250] [Second electrode 190] A second electrode 190 is provided on the organic layer 150. The second electrode 190 also serves as a cathode, which is an electron injection electrode. In this case, the material for the second electrode 190 may be a metal, an alloy, a conductive compound, or a combination thereof, each of which has a low work function.
[0251] The second electrode 190 may include at least one selected from the group consisting of 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 is not limited thereto. The second electrode 190 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0252] The second electrode 190 can have a single-layer structure having a single layer, or a multi-layer structure having multiple layers.
[0253] [Explanation of Figures 2 to 4] The organic electroluminescent device 20 of FIG. 2 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 are stacked in this order, the organic electroluminescent device 30 of FIG. 3 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in this order, and the organic electroluminescent device 40 of FIG. 4 has a structure in which a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are stacked in this order.
[0254] 2 to 4, the description of the first electrode 110, the organic layer 150, and the second electrode 190 refer to the description of FIG.
[0255] In the organic layer 150 of the organic electroluminescent device 20, 40, light generated in the light-emitting layer is extracted to the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210, and in the organic layer 150 of the organic electroluminescent device 30, 40, light generated in the light-emitting layer is extracted to the outside through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220.
[0256] The first capping layer 210 and the second capping layer 220 may serve to improve external light emission efficiency according to the principle of constructive interference.
[0257] The first capping layer 210 and the second capping layer 220 may be, independently of each other, an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer containing an organic material and an inorganic material.
[0258] At least one of the first capping layer 210 and the second capping layer 220 may independently include at least one material selected from the group consisting of carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may be optionally substituted with a substituent containing at least one element selected from the group consisting of O, N, S, Se, Si, F, Cl, Br, and I. According to an example, at least one of the first capping layer 210 and the second capping layer 220 may independently include an amine-based compound.
[0259] According to another example, at least one of the first capping layer 210 and the second capping layer 220 may include, independently of each other, a compound represented by Formula 201 or a compound represented by Formula 202.
[0260] According to yet another example, at least one of the first capping layer 210 and the second capping layer 220 may contain, independently of each other, a compound selected from the aforementioned compounds HT28 to HT33 and the following compounds CP1 to CP5, but is not limited thereto. [ka]
[0261] The organic electroluminescent device has been described above with reference to FIGS. 1 to 4, but is not limited thereto.
[0262] Each layer included in the hole transport region, the light emitting layer, and the electron transport region is formed in a predetermined region using various methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, ink jet printing, laser printing, and laser induced thermal imaging (LITI).
[0263] When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are formed by vacuum deposition, the deposition conditions are, for example, a deposition temperature of about 100° C. to about 500° C., a deposition time of about 10 -8 Torr ~ approx. 10 -3 The vacuum level is selected within the range of a vacuum of torr and a deposition rate of about 0.001 nm / sec to about 10 nm / sec, taking into consideration the material contained in the layer to be formed and the structure of the layer to be formed.
[0264] When each layer included in the hole transport region, the light-emitting layer, and each layer included in the electron transport region are formed by a spin coating method, the coating conditions are selected in consideration of the materials included in the layers to be formed and the structure of the layers to be formed, within the ranges of, for example, a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C.
[0265] [Device] The organic electroluminescent device may be included in various devices. Specifically, the device may include a thin film transistor including a source electrode, a drain electrode, and an active layer, and the organic electroluminescent device as described above. A first electrode of the organic electroluminescent device and one of the source electrode and the drain electrode of the thin film transistor are electrically connected to each other.
[0266] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0267] The active layer may include, but is not limited to, crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, and the like.
[0268] The device may further include a sealing part for sealing the organic electroluminescent element. The sealing part enables the organic electroluminescent element to display an image and blocks the organic electroluminescent element from permeating with outside air and moisture. The sealing part may be a sealing substrate including a transparent glass or plastic substrate. The sealing part may be a thin-film sealing layer including multiple organic layers and / or multiple inorganic layers. If the sealing part is a thin-film sealing layer, the entire device becomes flexible.
[0269] For example, the device is a light emitting device, an authentication device or an electronic device.
[0270] Light emitting devices are also used in various displays, light sources, and the like.
[0271] The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (for example, a fingertip, an eye, etc.). The authentication device may further include a biometric information collecting means in addition to the organic electroluminescent element as described above.
[0272] Electronic devices can also be used in, but are not limited to, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game consoles, medical equipment (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasound diagnostic devices, and endoscopic display devices), fish finders, various measuring instruments, gauges (e.g., gauges for vehicles, aircraft, and ships), and projectors. EXAMPLES
[0273] The organometallic compound and the organic electroluminescent device according to one embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples. In the synthesis examples below, in the expression "B was used instead of A," the molar equivalents of A and B are the same.
[0274] Synthesis Example 1: Synthesis of Compound BD1 Compound BD1 was synthesized with reference to Scheme I below. <Scheme I> [ka]
[0275] (1) Synthesis of intermediate [L1-1] Iodobenzene (1.0eq), imidazole (1.2eq), CuI (0.01eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfonate (0.1M) and stirred at 130°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L1-1] (yield 72%).
[0276] (2) Synthesis of intermediate [L1] Intermediate [L1-1] (1.0 eq), diphenyliodonium trifluoromethanesulfonate (1.3 eq), Cu(OAc) 2 (5 mol%) was dissolved in dimethylsulfonate (0.1M) and stirred at 100°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L1] (yield 60%).
[0277] (3) Synthesis of intermediate [L2-1] 1,3-Dibromobenzene (1.0eq), Imidazole (3.0eq), CuI (0.01eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfonate (0.1M) and stirred at 130°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L2-1] (yield 50%).
[0278] (4) Synthesis of intermediate [L2] Intermediate compound [L2-1] (1.0 eq) and iodomethane (5.0 eq) were dissolved in tetrahydrofuran (THF) (1.0 M) and stirred at 70°C for 12 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound [L2] (yield 66%).
[0279] (5) Synthesis of compound BD1 [L1](1.0eq), [L2](1.0eq), IrCl 3 xH 2 O (1.2 eq) and KOAc (0.5 eq) were dissolved in propionic acid (0.1 M) and stirred at 120° C. for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and compound BD1 (yield 20%) was synthesized using column chromatography.
[0280] Synthesis Example 2: Synthesis of compound BD7 Compound BD7 was synthesized with reference to Scheme II below. <Scheme II> [ka]
[0281] (1) Synthesis of intermediate [L1-1] Iodobenzene (1.0eq), imidazole (1.2eq), CuI (0.01eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfonate (0.1M) and stirred at 130°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L1-1] (yield 72%).
[0282] (2) Synthesis of intermediate [L1] Intermediate [L1-1] (1.0 eq), diphenyliodonium trifluoromethanesulfonate (1.3 eq), Cu(OAc) 2 (5 mol%) was dissolved in dimethylsulfonate (0.1M) and stirred at 100°C for 24 hours. The reaction mixture was cooled to room temperature and then extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L1] (yield 60%).
[0283] (3) Synthesis of intermediate [L3-1] 1,3-Dibromo-5-(trifluoromethyl)benzene (1.0 eq), imidazole (3.0 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfonate (0.1M) and stirred at 130°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L3-1] (yield 50%).
[0284] (4) Synthesis of intermediate [L3] Intermediate compound [L3-1] (1.0 eq) and iodomethane (5.0 eq) were dissolved in THF (1.0 M) and stirred at 70°C for 12 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound [L3] (yield 66%).
[0285] (5) Synthesis of compound BD7 [L1](1.0eq), [L3](1.0eq), IrCl 3 · x HO (1.2eq) and KOAc (0.5eq) were dissolved in propionic acid (0.1M) and stirred at 120°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and compound BD7 (yield 20%) was synthesized using column chromatography.
[0286] Synthesis Example 3: Synthesis of compound BD33 Compound BD33 was synthesized with reference to Scheme III below. <Scheme III> [ka]
[0287] (1) Synthesis of intermediate [L4-1] 2-Iodophenol (1.0eq), imidazole (1.2eq), CuI (0.01eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfonate (0.1M) and stirred at 130°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L4-1] (yield 72%).
[0288] (2) Synthesis of intermediate [L4] Intermediate [L4-1] (1.0eq), diphenyliodonium trifluoromethanesulfonate (1.3eq), Cu(OAc) 2 (5 mol%) was dissolved in dimethylsulfonate (0.1M) and stirred at 100°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L4] (yield 60%).
[0289] (3) Synthesis of intermediate [L5-1] 1,3-Dibromo-5-(trifluoromethyl)benzene (1.0 eq), benzimidazole (3.0 eq), CuI (0.01 eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfonate (0.1M) and stirred at 130°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [L5-1] (yield 50%).
[0290] (4) Synthesis of intermediate [L5] Intermediate compound [L5-1] (1.0 eq) and iodomethane (5.0 eq) were dissolved in THF (1.0 M) and stirred at 70°C for 12 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then subjected to column chromatography to synthesize intermediate compound [L5] (yield 66%).
[0291] (5) Synthesis of compound BD33 [L4](1.0eq), [L5](1.0eq), IrCl 3 xH 2 O (1.2eq) and KOAc (0.5eq) were dissolved in propionic acid (0.1M) and stirred at 120°C for 24 hours. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried over magnesium sulfate, concentrated, and then compound BD33 (yield 20%) was synthesized using column chromatography.
[0292] The compounds synthesized in Synthesis Examples 1 to 3 1 The 1 H NMR and MS / FAB results are shown in Table 1 below.
[0293] For compounds other than those shown in Table 1, those skilled in the art will be able to easily recognize the synthesis methods thereof by referring to the above-mentioned synthesis routes and raw materials. [Table 1]
[0294] Example 1 The substrate on which ITO / Ag / ITO was vapor-deposited as the anode was cut to a size of 50 mm x 50 mm x 0.7 mm, and ultrasonically cleaned for 5 minutes using isopropyl alcohol and pure water, respectively. After that, the substrate was cleaned by irradiating it with ultraviolet light and exposing it to ozone for 30 minutes, and the ITO substrate was then placed in a vacuum vapor deposition apparatus.
[0295] 2-TNATA was vacuum-deposited on the ITO substrate to form a 60 nm-thick hole injection layer, and then NPB was vacuum-deposited on the hole injection layer to form a 30 nm-thick hole transport layer.
[0296] On the hole transport layer, the compound H56 as a host and the compound BD1 as a dopant were co-deposited at a weight ratio of 10:1 to form a 25 nm-thick light-emitting layer.
[0297] BAlq was evaporated onto the light-emitting layer, a hole-blocking layer with a thickness of 5 nm was formed, and then Alq was evaporated onto the hole-blocking layer. 3 To fabricate an organic electroluminescent device, an organic electroluminescent device was fabricated by depositing LiF on the electron transport layer to form a 0.5 nm thick electron injection layer, and then depositing Al on the electron injection layer to form a 150 nm thick cathode.
[0298] Examples 2 and 3, Comparative Examples 1 to 3 An organic electroluminescent device was prepared in the same manner as in Example 1, except that the light-emitting layer was prepared using the compounds shown in Table 2 below.
[0299] Evaluation example The organic electroluminescence devices fabricated in Examples 1 to 3 and Comparative Examples 1 to 3 had a luminance of 1,000 cd / m 2 Driving voltage (V) and current density (mA / cm 2 ), luminous efficiency (cd / A), maximum emission wavelength (nm) and lifetime (T 90 ) were measured using a Keithley MU 236 and a luminance meter PR650, respectively, and the results are shown in Table 2. In Table 2, the life (T 90 ) is a measurement of the time it takes for the brightness to reach 90% of its initial brightness. [Table 2] [ka]
[0300] It can be seen from Table 2 that the current efficiency and lifetime of the organic electroluminescent devices of Examples 1-3 are superior to those of the organic electroluminescent devices of Comparative Examples 1-3.
[0301] Although the present invention has been described above with reference to the embodiments shown in the drawings, they are merely illustrative, and those skilled in the art will understand that various modifications and equivalent embodiments are possible therefrom. Therefore, the true technical scope of the present invention is defined by the technical ideas of the claims. [Explanation of symbols]
[0302] 10,20,30,40 Organic electroluminescent device 110 1st electrode 150 Organic layer 190 2nd electrode 210 First capping layer 220 Second Capping Layer
Claims
1. A first electrode; a second electrode facing the first electrode; an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer; An organic electroluminescent device comprising one or more organometallic compounds represented by the following chemical formula 1: M(L a ) n1 (L b ) n2 ・・・(Chemical formula 1) (In the above Chemical Formula 1, M is iridium; L a is selected from ligands represented by the following chemical formula 2: 【Chemistry 1】 ...(chemical formula 2) n1 is 1, L b is selected from ligands represented by the following formula 3: 【Chemistry 2】 ...(chemical formula 3) n2 is 1, L a and L b are different from each other, In the above Chemical Formula 2, A 1 and A 2 are, independently of each other, a C 6 carbocyclic group; X 1 , X 2 , X 3 , X 4 is C, Y 1 and Y 2 is C, T 1 , T 2 and T 3 are each independently a single bond or *-O-*', b1 to b3 are 1, R 1 R 1 to R 3 are each independently hydrogen or a substituted or unsubstituted C 1 -C 60 alkyl group; The R 1 ~R 3 may optionally be connected to adjacent groups by a single bond, -C(Q 4 ) (Q 5 ) -, -Si(Q 4 ) (Q 5 )-, -O-, -S-, -N(Q 4 ) -, -B(Q 4 )-, C(=O)-, -S(=O) 2 -, -S(=O)(Q 4 ) (Q 5 )- and P(=O)(Q 4 )-, and substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 forming a heterocyclic group or not bonding, a1 and a2 are each independently an integer selected from 0 to 10; a3 is 0, 1 or 2; The substituted C 5 -C30 carbocyclic group, substituted C 1 -C30 heterocyclic group, substituted C 1 -C 60 The substituents of the alkyl group are Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group and C 1 -C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, 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 C is substituted with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group and C 1 -C 60 Alkoxy group; C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, biphenylyl groups, and terphenylyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, biphenylyl group, terphenylyl 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 C is substituted with at least one selected from 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups, and terphenylyl groups; and -Si(Q 31 ) (Q 32 ) (Q 33 ), -N(Q 31 ) (Q 32 ), -B(Q 31 ) (Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 ) (Q 32 ); Q 1 ~Q 5 , Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 C substituted with alkyl group 6 -C 60 Aryl group, C 1 -C 60 is selected from the group consisting of heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups, and terphenylyl groups; * 1. * 2 and * 3 is a bonding position with the central metal M of Chemical Formula 1, * and *' are bonding positions to adjacent atoms, In the above Chemical Formula 3, A 11 is selected from the group consisting of a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group; L 1 and L 2 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R 14 )(R 15 )-*', *-Si(R 14 )(R 15 )-*', *-B(R 14 )-*', *-N(R 14 )-*' and *-P(R 14 )-*'; c1 and c2 are each independently 1, 2 or 3; X 11 , X 12 , X 13 and X 14 are each independently C or N; Y 11 is C or N; T 11 , T 12 and T 13 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*', *-Si(R 16 )(R 17 )-*', *-B(R 16 )-*', *-N(R 16 )-*' and *-P(R 16 )-*'; b11, b12 and b13 are each independently 1, 2 or 3; R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 each independently represent a hydrogen atom, a deuterium atom, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 selected from among heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 aryl groups, substituted or unsubstituted C 6 -C 60 aryloxy groups, substituted or unsubstituted C 6 -C 60 arylthio groups, substituted or unsubstituted C 2 -C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, -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 ); R 11 to R 13 are optionally bonded to adjacent groups via a single bond, -C(Q 4 )(Q 5 )-, -Si(Q 4 )(Q 5 )-, -O-, -S-, -N(Q 4 )-, -B(Q 4 )-, C(═O)-, -S(═O) 2 -, -S(═O)(Q 4 )(Q 5 )- or P(═O)(Q 4 )- to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, or are not bonded to each other; a11 is an integer selected from 0 to 10; a12 and a13 are each independently 0, 1, 2 or 3; The substituted C 5 -C 60 carbocyclic group, substituted C 1 -C 60 heterocyclic group, substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 2 -C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 heteroaryl group, 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 ), a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group substituted with at least one selected from the group consisting of -S(=O) 2 (Q 11 ), -S(=O) 2 (Q 11 ), and -P(=O)(Q 11 )(Q 12 ); C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, biphenylyl group and terphenylyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 10 aryloxy ...cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 cycloalkenyl group, a C 1 -C 10 60 arylthio groups, C 1 -C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups and terphenylyl groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(═O)(Q 31 ), -S(═O) 2 (Q 31 ) and -P(═O)(Q 31 )(Q 32 ); Q 1 to Q 5 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 substituted with a C 1 -C 60 alkyl group, selected from the group consisting of aryl groups, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenylyl groups, and terphenylyl groups; *1, *2 and *3 are bonding positions with the central metal M of Chemical Formula 1, * and *' are the bonding positions with adjacent atoms.)
2. the first electrode is an anode; the second electrode is a cathode; the organic layer further includes a hole transport region interposed between the first electrode and the light emitting layer, and an electron transport region interposed between the light emitting layer and the second electrode; the hole transport region includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof; The organic electroluminescent device of claim 1 , wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
3. The organic electroluminescent device according to claim 1 , wherein the light-emitting layer comprises the organometallic compound.
4. the light-emitting layer further comprises a host compound; the organometallic compound contained in the light-emitting layer is a dopant; The organic electroluminescent device according to claim 3 , wherein the content of the host compound in the light-emitting layer is greater than the content of the organometallic compound in the light-emitting layer.
5. the host compound includes a second compound and a third compound, the organometallic compound, the second compound, and the third compound are different from one another; the second compound and the third compound form an exciplex; The organic electroluminescent device according to claim 4 , wherein the organometallic compound and the second compound and / or the third compound do not form an exciplex.
6. an absolute value difference between a LUMO energy level of the organometallic compound and a LUMO energy level of the host compound is 0.1 to 1.0 eV; 5. The organic electroluminescent device according to claim 4, wherein a difference in absolute value between a HOMO energy level of the organometallic compound and a HOMO energy level of the host compound is 1.25 eV or less.
7. the light-emitting layer is a first color-emitting light-emitting layer, Between the first electrode and the second electrode, i) at least one second color light emitting light emitting layer is additionally included, or ii) at least one second color light emitting light emitting layer and at least one third color light emitting light emitting layer are additionally included, a maximum emission wavelength of the first color light, a maximum emission wavelength of the second color light, and a maximum emission wavelength of the third color light are the same or different from each other; a mixed color light obtained by mixing the first color light and the second color light, or the first color light, The organic electroluminescent device of claim 1 , wherein the second color light and the third color light are mixed together to emit mixed light.
8. An organometallic compound represented by the following chemical formula 1. M(L a ) n1 (L b ) n2 ・・・(Chemical formula 1) (In the above Chemical Formula 1, M is iridium; L a is selected from ligands represented by the following chemical formula 2: 【Chemistry 3】 ...(chemical formula 2) n1 is 1, L b is selected from ligands represented by the following formula 3: 【Chemistry 4】 ...(chemical formula 3) n2 is 1, L a and L b are different from each other, In Chemical Formula 2, A 1 and A 2 are, independently of each other, a C 6 carbocyclic group; X 1 , X 2 , X 3 , X 4 is C, Y 1 and Y 2 is C, T 1 , T 2 and T 3 are each independently a single bond or *-O-*', b1 to b3 are 1, R 1 R 1 to R 3 are each independently hydrogen or a substituted or unsubstituted C 1 -C 60 alkyl group; The R 1 ~R 3 may optionally be connected to adjacent groups by a single bond, -C(Q 4 ) (Q 5 ) -, -Si(Q 4 ) (Q 5 )-, -O-, -S-, -N(Q 4 ) -, -B(Q 4 )-, C(=O)-, -S(=O) 2 -, -S(=O)(Q 4 ) (Q 5 )- and P(=O)(Q 4 )-, and substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 forming a heterocyclic group or not bonding, a1 and a2 are each independently an integer selected from 0 to 10; a3 is 0, 1 or 2; The substituted C 5 -C30 carbocyclic group, substituted C 1 -C30 heterocyclic group, substituted C 1 -C 60 The substituents of the alkyl group are Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group and C 1 -C 60 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, 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 C is substituted with at least one selected from 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group and C 1 -C 60 Alkoxy group; C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocondensed polycyclic groups, biphenylyl groups, and terphenylyl groups; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, biphenylyl group, terphenylyl 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 C is substituted with at least one selected from 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups, and terphenylyl groups; and -Si(Q 31 ) (Q 32 ) (Q 33 ), -N(Q 31 ) (Q 32 ), -B(Q 31 ) (Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 ) (Q 32 ); Q 1 ~Q 5 , Q 11 ~Q 13 , Q 21 ~Q 23 , and Q 31 ~Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl group, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 C substituted with alkyl group 6 -C 60 Aryl group, C 1 -C 60 is selected from the group consisting of heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups, and terphenylyl groups; * 1. * 2 and * 3 is a bonding position with the central metal M of Chemical Formula 1, * and *' are bonding positions to adjacent atoms, In the above Chemical Formula 3, A 11 is selected from the group consisting of a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group; L 1 and L 2 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R 14 )(R 15 )-*', *-Si(R 14 )(R 15 )-*', *-B(R 14 )-*', *-N(R 14 )-*' and *-P(R 14 )-*'; c1 and c2 are each independently 1, 2 or 3; X 11 , X 12 , X 13 and X 14 are each independently C or N; Y 11 is C or N; T 11 , T 12 and T 13 are each independently selected from a single bond, *-O-*', *-S-*', *-C(R 16 )(R 17 )-*', *-Si(R 16 )(R 17 )-*', *-B(R 16 )-*', *-N(R 16 )-*' and *-P(R 16 )-*'; b11, b12 and b13 are each independently 1, 2 or 3; R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 each independently represent a hydrogen atom, a deuterium atom, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 selected from among heterocycloalkenyl groups, substituted or unsubstituted C 6 -C 60 aryl groups, substituted or unsubstituted C 6 -C 60 aryloxy groups, substituted or unsubstituted C 6 -C 60 arylthio groups, substituted or unsubstituted C 2 -C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, -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 ); R 11 to R 13 are optionally bonded to adjacent groups via a single bond, -C(Q 4 )(Q 5 )-, -Si(Q 4 )(Q 5 )-, -O-, -S-, -N(Q 4 )-, -B(Q 4 )-, C(═O)-, -S(═O) 2 -, -S(═O)(Q 4 )(Q 5 )- or P(═O)(Q 4 )- to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, or are not bonded to each other; a11 is an integer selected from 0 to 10; a12 and a13 are each independently 0, 1, 2 or 3; The substituted C 5 -C 60 carbocyclic group, substituted C 1 -C 60 heterocyclic group, substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 2 -C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 heteroaryl group, 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 ), a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group substituted with at least one selected from the group consisting of -S(=O) 2 (Q 11 ), -S(=O) 2 (Q 11 ), and -P(=O)(Q 11 )(Q 12 ); C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, biphenylyl group and terphenylyl group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 6 -C 60 aryloxy group, C 6 -C 60 arylthio group, C 1 -C 60 a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 10 aryloxy ...cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 aryloxy group, a C 6 -C 10 cycloalkenyl group, a C 1 -C 10 60 arylthio groups, C 1 -C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenylyl groups and terphenylyl groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(═O)(Q 31 ), -S(═O) 2 (Q 31 ) and -P(═O)(Q 31 )(Q 32 ); Q 1 to Q 5 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 substituted with a C 1 -C 60 alkyl group, selected from the group consisting of aryl groups, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic hetero-fused polycyclic groups, biphenylyl groups, and terphenylyl groups; *1, *2 and *3 are bonding positions with the central metal M of Chemical Formula 1, * and *' are the bonding positions with adjacent atoms.)
9. Said T 1 and T 2 At least one of the groups is *-O-*', Said T 3 The organometallic compound of claim 8 , wherein is a single bond.
10. The R 1 to R3 are each independently Hydrogen, and C1-C 20 Alkyl groups; C substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenylyl group, and a terphenylyl group; 1 -C 20 Alkyl groups; 9. The organometallic compound of claim 8, wherein
11. The organometallic compound according to claim 8, wherein the chemical formula 2 is represented by the following chemical formula 2-1 or 2-2. 【Chemistry 5】 ...(Chemical formula 2-1) 【Chemistry 6】 ...(Chemical formula 2-2) (In the above Chemical Formula 2-1 and Chemical Formula 2-2, R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are each independently hydrogen or a substituted or unsubstituted C 1 -C 60 alkyl group.
12. The organometallic compound according to claim 8, wherein the formula 3 is represented by any one of the following formulas 3-1 and 3-2: 【Chemistry 7】 ...(Chemical formula 3-1) 【Chemistry 8】 ...(Chemical formula 3-2) (In the above Chemical Formula 3-1 and Chemical Formula 3-2, A 11 is C 6 -C 60 Aryl groups and C 1 -C 60 heteroaryl groups, L 1 and L 2 are each independently a single bond, *-O-*', *-S-*', *-C(R 14 ) (R 15 )-*', *-Si(R 14 ) (R 15 )-*', *-B(R 14 )-*', *-N(R 14 )-*' and *-P(R 14 )-*', c1 and c2 are each independently 1, 2 or 3; Y 11 is C or N, T 11 , T 12 and T 13 are each independently a single bond, *-O-*', *-S-*', *-C(R 16 ) (R 17 )-*', *-Si(R 16 ) (R 17 )-*', *-B(R 16 )-*', *-N(R 16 )-*' and *-P(R 16 )-*', b11, b12 and b13 are each independently 1, 2 or 3; R 11 , R 12a , R 12b , R 12c , R 12d , R 12e , R 12f , R 12g , R 13a , R 13b , R 13c , R 13d , R 13e , R 13f , R 13g , R 14 , R 15 , R 16 and R 17 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 Alkyl group, substituted or unsubstituted C 2 -C 60 Alkenyl group, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy group, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 2 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy group, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 2 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a 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 ) is selected from The R 11 , R 12a , R 12b , R 12c , R 12d , R 12e , R 12f , R 12g , R 13a , R 13b , R 13c , R 13d , R 13e , R 13f , R 13g may optionally be connected to adjacent groups by a single bond, -C(Q 4 ) (Q 5 ) -, -Si(Q 4 ) (Q 5 )-, -O-, -S-, -N(Q 4 ) -, -B(Q 4 )-, C(=O)-, -S(=O) 2 -, -S(=O)(Q 4 ) (Q 5 )- and P(=O)(Q 4 )-, and substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 forming a heterocyclic group or not bonding, a11 is an integer selected from 0 to 10.
13. The organometallic compound according to claim 8, which is selected from the following compounds BD1 to BD48. 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】
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