Organometallic compound and organic light-emitting device including same
The development of an organometallic compound with specific metal-ligand configurations addresses the efficiency and longevity issues in organic light-emitting devices by enhancing electron donating properties and stabilizing the metal-ligand bond, resulting in improved device performance.
Patent Information
- Application Number
- JP2020081279
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2019-05-10
- Filing Date
- 2020-05-01
- Publication Date
- 2024-12-17
- Estimated Expiration
- 2040-05-01
AI Technical Summary
Existing organic light-emitting devices lack efficient organometallic compounds that enhance performance in terms of efficiency and longevity.
Development of an organometallic compound represented by Chemical Formula 1, featuring specific metal-ligand configurations, which improves electron donating properties and stabilizes the bond between metal and ligand, leading to higher efficiency and longer life of organic light-emitting devices.
The organometallic compound enhances the efficiency and extends the lifespan of organic light-emitting devices by improving electron donating properties and stabilizing the metal-ligand bond, resulting in improved performance.
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Abstract
Description
[Technical field]
[0001] The present invention relates to an organometallic compound and an organic light-emitting device containing the same. [Background technology]
[0002] Organic light-emitting devices are self-luminous devices that, compared with conventional devices, have a wider viewing angle, superior contrast, shorter response time, superior luminance, driving voltage and response speed characteristics, and are capable of multiple colors.
[0003] The organic light emitting device may have a structure in which a first electrode is disposed on the 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 the holes and electrons recombine in the light emitting layer region to generate excitons. Light is generated as the excitons change from an excited state to a ground state. Summary of the Invention [Problem to be solved by the invention]
[0004] An object of the present invention is to provide a novel organometallic compound and an organic light-emitting device containing the same. [Means for solving the problem]
[0005] According to one aspect, there is provided an organometallic compound represented by the following formula 1: M(L 1 ) n1 (L 2 ) n2 1 In Formula 1, M is selected from the group consisting of iridium (Ir), rhodium (Rh), cobalt (Co) and meitnerium (Mt); L 1is a ligand represented by the chemical formula 2-1, n1 is 1, 2 or 3, and when n1 is 2 or more, two or more L 1 may be the same or different from each other, L 2 is an organic ligand, n2 is 0, 1 or 2, and when n2 is 2 or more, two or more L 2 may be the same or different from each other, n1+n2 is 2 or 3, [ka] 2-1 In chemical formula 2-1, A 1 is C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, X 1 ~X 4 are independent of each other, C(R 2 ) or N, R 1 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 C6 -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 1 )(Q 2 )(Q 3 ), -N(Q 1 )(Q 2 ), -B(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q1)(Q2), R 2 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 C6 -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 1 )(Q 2 )(Q 3 ), -N(Q 1 )(Q 2 ), -B(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q1)(Q2), b1 is selected from the group consisting of integers from 1 to 10; The above 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 -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 1 -C 60At least one substituent which substitutes a substituent selected from a heteroaryl group, a substituted monovalent non-aromatic fused polycyclic group, and a substituted monovalent non-aromatic fused polycyclic heterocyclic group is 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 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 ), -P(Q11)(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, C2 -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 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 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 heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -P(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 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 ), -P(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 3 , Q 11 ~Q13 , 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 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heterocyclic polycyclic groups; C substituted with at least one selected from deuterium, -F and a cyano group 1 -C 60 Alkyl group; C substituted with at least one selected from deuterium, -F and cyano group 6 -C 60 selected from among an aryl group, a biphenylyl group, or a terphenylyl group, * indicates the binding site for M.
[0006] According to another embodiment, a liquid crystal display device includes a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer including an emitting layer, An organic light emitting device is provided that includes one or more organometallic compounds represented by Chemical Formula 1. Effect of the Invention
[0007] Organic light emitting devices including the organometallic compounds of the present invention can have high efficiency and long life. [Brief description of the drawings]
[0008] [Figure 1] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. [Diagram 2] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. [Diagram 3] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. [Figure 4] 1 is a schematic diagram illustrating a structure of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0009] The organometallic compound of the present invention is represented by the following formula 1: M(L 1 ) n1 (L 2 ) n2 1 In Formula 1, M is selected from the group consisting of iridium (Ir), rhodium (Rh), cobalt (Co) and meitnerium (Mt). In formula 1, L 1 is a ligand represented by the chemical formula 2-1, n1 is 1, 2 or 3, and when n1 is 2 or more, two or more L 1 may be the same or different, L 2 is an organic ligand, n2 is 0, 1 or 2, and when n2 is 2 or more, two or more L 2 may be the same or different, n1+n2 is 2 or 3. [ka] 2-1
[0010] According to one embodiment, n1 is 1, n2 is 1, and L 2 may be a tetracoordinate ligand.
[0011] In chemical formula 2-1, A 1 is C 5 -C 60 Carbocyclic structures and C 1 -C 60 The heterocyclic structure is selected from the group consisting of aryl, aryloxy ...
[0012] In Chemical Formula 2-1, * is a bonding site with M.
[0013] According to one embodiment, in formula 2-1, A 1 may be a ring structure that may be selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, thiophene, furan, pyrrole, indole, indene, benzosilole, benzothiophene, benzofuran, carbazole, fluorene, dibenzosilole, dibenzothiophene, dibenzofuran, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline, 5,6,7,8-tetrahydroquinoline, and benzoquinazoline.
[0014] For example, A 1 may be, but is not limited to, benzene or pyridine.
[0015] In chemical formula 2-1, X 1 ~X 4 are independent of each other, C(R 2 ) or N.
[0016] According to one embodiment, in formula 2-1, X 1 ~X 4 is C(R 2 ) may also be used.
[0017] In chemical formula 2-1, R 1 , independently of each other, 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 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 1 )(Q 2 )(Q 3 ), -N(Q 1 )(Q2 ), -B(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 )(Q 2 ) is selected. In chemical formula 2-1, R 2 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 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60Heteroaryl 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 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 )(Q 2 ) is selected.
[0018] According to one embodiment, in formula 2-1, R 1 are each independently 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 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, -Si(Q31 )(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 ) replaced with at least one selected from 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group groups, indolyl groups, indazolyl groups, purinyl groups, quinolinyl groups, isoquinolinyl groups, benzoquinolinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, carbazolyl groups, acridinyl groups, phenanthrolinyl groups, benzimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, oxadiazolyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, imidazopyridinyl groups and imidazopyrimidinyl groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindo group, -aryl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, acridinyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl 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 )(Q32 a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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 pyridazin ... nyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, acridinyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and -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 ), -P(Q 1 )(Q 2 ) and -P(=O)(Q 1 )(Q 2 ); R 2 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, C2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl 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 ) replaced with at least one selected from 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group groups, indolyl groups, indazolyl groups, purinyl groups, quinolinyl groups, isoquinolinyl groups, benzoquinolinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, carbazolyl groups, acridinyl groups, phenanthrolinyl groups, benzimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, oxadiazolyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, imidazopyridinyl groups and imidazopyrimidinyl groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindo group, -aryl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, acridinyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl 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 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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 pyridazin ... nyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, acridinyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and -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 ), -P(Q 1 )(Q 2 ) and -P(=O)(Q 1 )(Q 2 ); Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 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 20 Aryl group, C 1 -C 20 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; C substituted with at least one selected from deuterium, -F and a cyano group 1 -C 20 Alkyl groups; C substituted with at least one selected from deuterium, -F and a cyano group 6 -C 20 Aryl groups; and biphenylyl groups and terphenylyl groups.
[0019] For example, R 1 may be, but is not limited to, -F.
[0020] According to one embodiment, i) in formula 2-1, X 1 and X 2 is C(R 2 ) and R 2 is hydrogen, or ii) In formula 2-1, X 3 and X 4 is C(R 2 ) and R 2 may be a methyl group, a t-butyl group or an iso-propyl group.
[0021] In Chemical Formula 2-1, b1 is selected from integers of 1 to 10. When b1 is 2 or more, R 1 may be the same or different, In chemical formula 2-1, b1 R 1 In the formula, two adjacent ones are optionally bonded to each other and each is a substituted or unsubstituted C 5 -C 30 Carbocyclic ring structure or substituted or unsubstituted C 1 -C 30 Heterocyclic structures can be formed.
[0022] According to one embodiment, L 1 may be a ligand selected from the groups represented by the following chemical formulas 2-1(1) and 2-1(2): [ka] 2-1(1) [ka] 2-1(2) In the chemical formulas 2-1(1) and 2-1(2), R 1a ~R 1d , and R 2a ~R 2d For an explanation of 1 and R 2 Please refer to the explanation of * indicates the binding site for M.
[0023] For example, in formulas 2-1(1) and 2-1(2), R 1b and R 1d may be, but is not limited to, hydrogen or -F.
[0024] According to one embodiment, L 2 may be a ligand represented by formula 2-2 or 2-3: [ka] 2-2 [ka] 2-3 Chemical formula 2-2 or 2-3: X 21 and X 22 are independent of each other, C(R 23 ) or N, X 23 and X 24 are independent of each other, C(R 24 ) or N, A 11 ~A 14 , A 21 and A 22 , R 11 ~R 16 , R 21 ~R 26 , b11 to b14, b21 to b22, and * are the same as those in the above A 1 , R 1 See explanations for b1 and *. n11 and n21 are each independently selected from integers of 2 to 6.
[0025] According to one embodiment, in the formula 2-2 or 2-3, A 11 ~A 14 , A 21 and A 22may each independently be a ring structure selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, thiophene, furan, pyrrole, indole, indene, benzosilole, benzothiophene, benzofuran, carbazole, fluorene, dibenzosilole, dibenzothiophene, dibenzofuran, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline, 5,6,7,8-tetrahydroquinoline, and benzoquinazoline.
[0026] For example, in chemical formula 2-2, A 11 ~A 14 may each independently be a ring structure selected from benzene, pyridine, and pyrazine, but is not limited thereto.
[0027] For example, in chemical formula 2-2, A 11 ~A 12 may be, but is not limited to, a benzene ring.
[0028] For example, in formula 2-3, A 21 and A 22 may be, but is not limited to, a benzene ring.
[0029] According to one embodiment, in formula 2-2, X 21 and X 22 is C(R 23 ) and in formula 2-3, X 23 and X 24 is C(R 24 ) may also be used.
[0030] According to one embodiment, in formula 2-2 or 2-3, R 11 ~R 14 , and R 21 ~R 24 are each independently 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 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 alkoxy groups; R 15 ~R 16 , and R 25 ~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, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 alkoxy groups; R 11 ~R 16 , and R 21 ~R 26 are, independently of each other, deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, -Si(Q 31 )(Q32 )(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 ) replaced with at least one selected from 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group groups, indolyl groups, indazolyl groups, purinyl groups, quinolinyl groups, isoquinolinyl groups, benzoquinolinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, carbazolyl groups, acridinyl groups, phenanthrolinyl groups, benzimidazolyl groups, benzofuranyl groups, benzothiophenyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, oxadiazolyl groups, triazinyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, benzocarbazolyl groups, dibenzocarbazolyl groups, imidazopyridinyl groups and imidazopyrimidinyl groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2, -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindo group, -aryl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, acridinyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl 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 32a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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 pyridazin ... nyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, acridinyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and -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 ), -P(Q 1 )(Q 2 ) and -P(=O)(Q 1 )(Q 2 ); Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 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 20 Aryl group, C 1 -C 20 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; C substituted with at least one selected from deuterium, -F and a cyano group 1 -C 20 Alkyl groups; C substituted with at least one selected from deuterium, -F and a cyano group 6 -C 20 Aryl groups; and biphenyl groups and terphenyl groups.
[0031] For example, in formula 2-2, R 11 and R 12 may be, independently of each other, hydrogen, -F, -Cl, -Br, -I, a methyl group, or an iso-propyl group, but are not limited thereto.
[0032] For example, in formula 2-2, R 13 ~R 16 may be, but is not limited to, hydrogen.
[0033] For example, in formula 2-3, R 21 and R 22 may be, independently of each other, hydrogen, -F, -Cl, -Br, -I, a methyl group, or an iso-propyl group, but are not limited thereto.
[0034] For example, in formula 2-3, R 25 and R 26 may be, but is not limited to, hydrogen.
[0035] For example, n11 in Chemical Formula 2-2 may be 4, and n21 in Chemical Formula 2-3 may be 4, but is not limited thereto.
[0036] For example, in formula 2-3, X 21 and X 22 is C(R 23 ) and X 23 and X 24 is C(R 24 ) and R 23 and R 24 are identical to each other, and R 23 and R 24 may be, but is not limited to, hydrogen or a methyl group.
[0037] According to one embodiment, L 2 may be a ligand selected from groups represented by the following chemical formulas 2-2(1) to 2-2(3) and chemical formula 2-3(1): [ka] 2-2(1) [ka] 2-2(2) [ka] 2-2(3) [ka] 2-3(1) In chemical formulas 2-2(1) to 2-2(3) and chemical formula 2-3(1), R11a ~R 11d , R 12a ~R 12d , R 13a ~R 13d , R 14a ~R 14d , R 21a ~R 21d , R 22a ~R 22d , R 23a ~R 23b , and R 24a ~R 24b For an explanation of 11 ~R 16 , R 21 ~R 26 , see the explanation for n11 and n21, * indicates the binding site for M.
[0038] According to one embodiment, the organometallic compound may be selected from the following compounds BD1 to BD59, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka]
[0039] The organometallic compound represented by Chemical Formula 1 contains an imidazopyrazine-based ligand represented by Chemical Formula 2-1, which improves the electron donating property, improves the bond dissociation energy (BDE) of the compound, and stabilizes the bond between the metal and the ligand. Therefore, the life of electronic devices (e.g., organic light-emitting devices) containing the organometallic compound is improved.
[0040] In addition, the organometallic compound represented by Chemical Formula 1 can improve the electron donating property, improve the bond dissociation energy (BDE) of the compound, and stabilize the bond between the metal and the ligand by including an imidazole-based tetracoordinate ligand represented by Chemical Formula 2-2 or 2-3, thereby improving the life of electronic devices (e.g., organic light-emitting devices) that include the organometallic compound.
[0041] The organometallic compound can emit blue light. For example, the organometallic compound can emit blue light (back-emission CIE 1000 nm) having a maximum emission wavelength of 440 nm or more and 490 nm or less. x,y The color coordinates of the organic light emitting device may be, but are not limited to, 0.05, 0.3 to 0.18, 0.08. Therefore, the organometallic compound represented by Chemical Formula 1 may be useful for preparing an organic light emitting device that emits blue light.
[0042] 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.
[0043] At least one of the organometallic compounds represented by Chemical Formula 1 is used between a pair of electrodes of an organic light emitting device. For example, the organometallic compound is included in an emission layer. The organometallic compound included in the emission layer may act as a dopant. Alternatively, the organometallic compound represented by Chemical Formula 1 may be used as a capping material located outside a pair of electrodes of the organic light emitting device.
[0044] Thus, there is provided an organic light-emitting device comprising a first electrode, a second electrode opposed to the first electrode, and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, the organic light-emitting device comprising one or more of the organometallic compounds described above.
[0045] In this specification, "(the organic layer) contains one or more organometallic compounds" can also be interpreted as "(the organic layer) may contain one organometallic compound belonging to the category of Chemical Formula 1, or two or more different organometallic compounds belonging to the category of Chemical Formula 1."
[0046] For example, the organic layer may contain only compound 1 as an organometallic compound. In this case, compound 1 may be present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may contain the above-mentioned compound 1 and compound 2 as organometallic compounds. In this case, compound 1 and compound 2 may be present in the same layer (for example, compound 1 and compound 2 are both present in the light-emitting layer) or may be present in different layers (for example, compound 1 is present in the light-emitting layer and compound 2 is present in the electron transport region).
[0047] According to one embodiment, 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 assist layer, an electron blocking layer, or any combination thereof; The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0048] In this specification, the term "organic layer" refers to a single and / or multiple layers interposed between a first electrode and a second electrode in an organic light-emitting device. The material contained in the "organic layer" is not limited to an organic material.
[0049] According to one embodiment, the light-emitting layer may include an organometallic compound.
[0050] According to one embodiment, the light-emitting layer further comprises one or more of a second compound and a third compound; the organometallic compound, the second compound, and the third compound are different from one another; When the light-emitting layer contains both the second compound and the third compound, the second compound and the third compound form an exciplex, The organometallic compound and the second compound and / or the third compound do not form an exciplex.
[0051] For example, the light-emitting layer may include both the second compound and the third compound, or the light-emitting layer may include the second compound and not the third compound, or the light-emitting layer may include the third compound and not the second compound.
[0052] According to one embodiment, the second compound is represented by the following formula 3: The third compound is represented by the following formula 4: [ka] 3 [ka] 4 In formulas 3 and 4, X 31 is C(R 31 ) and N, 32 is C(R 32 ) and N, 33 is C(R 33 ) and N, 34 is C(R 34 ) and N, 35 is C(R 35 ) and N, 36 is C(R 36 ) and N, 31 ~X 36 At least one of is N, 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 -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 C 1 -C 60 Heteroaryloxy groups, substituted or unsubstituted C 1 -C 60 Heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q2 ), -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 ) b37 is a group represented by L 31 is a substituted or unsubstituted C 5 -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 6 -C 60Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio groups, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy groups, substituted or unsubstituted C 1 -C 60 Heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), b37 is selected from the group consisting of integers from 1 to 10; A 41 and A 42 are independent of each other, C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, X 41 is a single bond, O, S, B(R 43 ), N(R 43 ), C(R 43 )(R 44 ) and Si(R 43 )(R 44 ), and X 42 is a single bond, O, S, B(R 45 ), N(R 45 ), C(R 45 )(R 46 ) and Si(R45 )(R 46 ), and X 41 and X 42 but at the same time not a single bond, R 41 ~R 46 are independent of each other, *-(L 41 ) a41 -(R 47 ) b47 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 -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 C 1 -C 60 Heteroaryloxy groups, substituted or unsubstituted C 1 -C 60 Heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q2 )(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 41 ~R 46 At least one of the following is *-(L 41 ) a41 -(R 47 ) b47 is a group represented by L 41 is a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 heterocyclic groups, a41 is selected from integers of 0 to 6; R 47 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 10Heterocycloalkenyl 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 C 1 -C 60 Heteroaryloxy groups, substituted or unsubstituted C 1 -C 60 Heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 ), -B(Q 1 )(Q 2 ), -N(Q 1 )(Q 2 ), -P(Q 1 )(Q 2 ), -C(=O)(Q 1 ), -S(=O)(Q 1 ), -S(=O) 2 (Q 1 ), -P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), b47 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 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 groups, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 is selected from the group consisting of a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group; * indicates a bonding site with an adjacent atom.
[0053] For example, X 31 C(R 31 ) and X 33 C(R 33 ) and X 35 C(R 35 ) or X 32 C(R 32 ) and X 34 C(R 34 ) and X 36 C(R 36 ) may also be used.
[0054] For example, a41 may be 1 or greater.
[0055] For example, the second compound may be selected from among ETH1 to ETH80 below, and the third compound may be selected from among HTH1 to HTH28 below: [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0056] According to one embodiment, in a time-resolved electroluminescence (TREL) spectrum of the organic light-emitting device, the decay time of delayed fluorescence may be 50 ns or more.
[0057] As described above, the second compound and the third compound can form an exciplex, and the exciplex has a maximum emission wavelength (λ 2 ) in its photoluminescence (PL) spectrum. max ) may be greater than or equal to 390 nm and less than or equal to 500 nm.
[0058] Furthermore, in the emission spectrum of the exciplex, the maximum emission wavelength of the organometallic compound can be suppressed to 5 nm to 10 nm.
[0059] The absolute value difference between the LUMO (lowest unoccupied molecular orbital) energy level of the organometallic compound and the LUMO energy level of the second compound or the third compound may be 0.1 eV to 10 eV.
[0060] The absolute difference between the HOMO energy level of the organometallic compound and the HOMO energy level of the second compound or the third compound may be 1.25 eV or less.
[0061] According to another aspect, there is provided a flat panel display device including an organic light emitting device and a thin film transistor.
[0062] According to one embodiment, the thin film transistor includes a source electrode and a drain electrode, and the first electrode of the organic light emitting element is also electrically connected to the source electrode or the drain electrode.
[0063] [Explanation of Figure 1] 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0064] Hereinafter, a structure and a method for manufacturing an organic light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG.
[0065] [First electrode 110] 1, a substrate may be additionally 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.
[0066] The first electrode 110 may be formed by providing a first electrode material on the substrate using, for example, a deposition method or a sputtering method. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function so that holes can be easily injected.
[0067] The first electrode 110 may be 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 Alternatively, to form the first electrode 110, which is a semi-transmissive electrode or a reflective electrode, the material for the first electrode may be 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.
[0068] 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, but not limited to, a three-layer structure of ITO / Ag / ITO.
[0069] [Organic layer 150] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes an emitting layer.
[0070] The organic layer 150 may further include a hole transport region interposed between the first electrode 110 and the light emitting layer, and an electron transport region interposed between the light emitting layer and the second electrode 190.
[0071] [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.
[0072] 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).
[0073] 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 thereto.
[0074] 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(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following formula 201, and a compound represented by the following formula 202: [ka] [ka] [ka] 201 [ka] 202 In chemical formulas 201 and 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 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; 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 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 It may be selected from among a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0075] For example, in formula 202, R 201 and R 202 are optionally linked to each other via a single bond, a dimethyl group, a methylene group, or a diphenyl group, a methylene group, to form R 203 and R 204 are optionally bonded to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
[0076] According to one embodiment, in formulas 201 and 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 10Phenyl 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 32 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, 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 -C10 It may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0077] According to another embodiment, xa1 to xa4 may be 0, 1 or 2, independently of each other.
[0078] According to yet other embodiments, xa5 may be 1, 2, 3 or 4.
[0079] According to yet another embodiment, R 201 ~R 204 , and Q 201 are 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 10Phenyl 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 32 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, or a chrysenyl group, each of which is substituted with at least one selected from the group consisting of , naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, thiophenyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl groups; The aforementioned Q 31 ~Q 33 For the explanation of the above, please refer to the description in this specification.
[0080] According to yet another embodiment, in formula 201, R 201 ~R 203 In which at least one, independently of the others, 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 10 The phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one selected from the group consisting of a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; but is not limited thereto.
[0081] According to yet another embodiment, in formula 202, i) R 201 and R 202 are also bonded to each other via a single bond, and / or ii) R 203 and R 204 are also bonded to each other via a single bond.
[0082] According to yet another embodiment, 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 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenylyl group, terphenylyl group, C 1 -C 10 The 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 thereto.
[0083] The compound of formula 201 may be represented by the following formula 201A: [ka] 201A
[0084] For example, the compound represented by formula 201 may be represented by the following formula 201A(1), but is not limited thereto: [ka] 201A(1)
[0085] As yet another example, the compound represented by formula 201 may be represented by, but is not limited to, the following formula 201A-1: [ka] 201A-1
[0086] Meanwhile, the compound represented by formula 202 may be represented by the following formula 202A: [ka] 202A
[0087] According to yet another embodiment, the compound represented by formula 202 may be represented by formula 202A-1: [ka] 202A-1
[0088] Chemical formulas 201A, 201A(1), 201A-1, 202A and 202A-1, L 201 ~L 203 , xa1 to xa3, xa5, and R 202 ~R 204 For the description of R 211 and R 212 For the explanation of R203, refer to the explanation of R203 in this specification. 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, biphenylyl group, terphenylyl group, C 1 -C 10Phenyl 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 , 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.
[0089] The hole transport region may include at least one compound selected from the following compounds HT1 to HT39, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0090] The thickness of the hole transport region may be about 10 nm to about 1,000 nm, for example, about 10 nm to about 100 nm. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about 10 nm to about 900 nm, for example, about 10 nm to about 100 nm, and the thickness of the hole transport layer may be 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, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage.
[0091] The light emitting auxiliary layer is a layer that compensates for an optical resonance distance according to the wavelength of light emitted from the light emitting layer to improve 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 include the above-mentioned materials.
[0092] [p-dopant] In addition to the above-mentioned materials, the hole transport region may further include a charge generating material to improve electrical conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.
[0093] The charge generating material can be, for example, a p-dopant.
[0094] According to one embodiment, the LUMO of the p-dopant is lower than -3.5 eV.
[0095] 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.
[0096] For example, the p-dopant is 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; 1,4,5,8,9,12-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and The compound may include at least one selected from the following compounds represented by the following formula 221; but is not limited thereto: <hat-cn>
change
[0097] [Light-emitting layer in organic layer 150] When the organic light emitting device 10 is a full-color organic light emitting device, the light emitting layer is patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each individual subpixel, or 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.
[0098] The light-emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant. The phosphorescent dopant may include an organometallic compound represented by Chemical Formula 1 herein.
[0099] In the light-emitting layer, the content of the dopant is generally selected in the range of about 0.01 parts by weight to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.
[0100] The thickness of the light-emitting layer may be 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.
[0101] [Host in the light-emitting layer] The host may include a second or third compound as described above.
[0102] In addition, the host may include a compound represented by the following formula 301: [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 301 In 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 may be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.
[0103] According to one embodiment, in formula 301, Ar 301 teeth, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, indenoanthracenyl, 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, 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 a naphthyl 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, a dibenzofuranyl group and a dibenzothiophenyl group; Q 31 ~Q 33 are independent of each other, C 1 -C 10 Alkyl group, C 1 -C 10 It may be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group.
[0104] In the formula 301, if xb11 is 2 or more, 2 or more Ar 301 are also bonded to each other via a single bond.
[0105] According to other embodiments, the compound represented by formula 301 may be represented by formula 301-1 or 301-2: [ka] 301-1 [ka] 301-2 Chemical formula 301-1 to 301-2: A 301 ~A 304 are ring structures selected independently from 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 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, biphenyl group, terphenyl 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.
[0106] For example, in formulas 301, 301-1 and 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.
[0107] As another example, in formulas 301, 301-1 and 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.
[0108] 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.
[0109] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-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), and the following compounds H1 to H55, but is not limited thereto: [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0110] Alternatively, the host may include at least one of a silicon-containing compound (eg, BCPDS used in the examples below) and a phosphine oxide-containing compound (eg, POPCPA used in the examples below).
[0111] The host may include only one type of compound, or may include two or more different compounds (for example, the host in the following example is composed of BCPDS and POPCPA).
[0112] [Phosphorescent dopants included in the light-emitting layer of organic layer 150] The phosphorescent dopant herein may include an organometallic compound represented by Formula 1:
[0113] The phosphorescent dopant may further include an organometallic complex represented by the following formula 401: M'(L 401 ) xc1 (L 402 ) xc2 401 In chemical formula 401, 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, two or more L401 may be the same or different from each other; 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, [ka] 402 In the chemical formula 402, X 401 ~X 404 are, independently of each other, nitrogen or carbon; X 401 and X 403 are linked via a single or double bond, and X 402 and X 404 is linked via a single or double bond, A 401 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=*', and the above Q 411 and Q 412 is hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; X 406 is a single bond, O or S, R 401 and R 402 are each independently 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, and 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 binding sites with M' in chemical formula 401.
[0114] According to one embodiment, in formula 402, A 401 and A 402 may each independently be 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.
[0115] According to another embodiment, in formula 402, i) X 401 is nitrogen, and X 402 is carbon, or ii) X 401 and X 402 and may both be nitrogen.
[0116] According to yet another embodiment, in formula 402, R 401 and R 402 are independent of each other, 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, biphenyl group, terphenyl 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 may be selected from, but is not limited to, an alkoxy group, a phenyl group, a biphenylyl group, and a naphthyl group.
[0117] According to yet another embodiment, in formula 401, when xc1 is 2 or more, 2 or more L 401 In this case, two A 401 is optionally a linking group, X 407 or two A 402 is optionally a linking group, X 408 (See compounds PD1 to PD4 and 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 biphenyl group, a terphenyl group, or a naphthyl group. Chemical Formula 401 L 402 may be any monovalent, divalent or trivalent organic ligand. For example, L 402 may be selected from, but is not limited to, halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., picolinates), -C(=O), isonitriles, -CN, and phosphorous-containing materials (e.g., phosphines, phosphites).
[0118] Alternatively, the phosphorescent dopant may be selected from, for example, but not limited to, the following compounds PD1 to PD25: [ka] [ka] [ka]
[0119] [Fluorescent dopants in the light-emitting layer] The fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0120] The fluorescent dopant may include a compound represented by formula 501: [ka] 501 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 heteropolycyclic group; xd4 may be selected from integers from 1 to 6.
[0121] According to one embodiment, the compound represented by formula 501 is Ar 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 may be selected from the group consisting of naphthalenyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, indenoanthracenyl, and indenophenanthrenyl groups, each of which is substituted with at least one selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl, and naphthyl groups.
[0122] According to another embodiment, in formula 501, L 501 ~L 503 are independent of each other, phenylene groups, naphthylene groups, fluorenylene groups, spiro-bifluorenylene groups, benzofluorenylene groups, dibenzofluorenylene groups, phenanthrenylene groups, anthracenylene groups, fluoranthenylene groups, triphenylenylene groups, pyrenylene groups, chrysenylene groups, perylenylene groups, pentaphenylene groups, hexacenylene groups, pentacenylene 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, 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, 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 and 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, a pyridinylene group;
[0123] According to yet another embodiment, 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,
[0124] The aforementioned Q 31 ~Q 33 is C 1 -C 10 Alkyl group, C 1 -C 10 It may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0125] According to yet another embodiment, xd4 in formula 501 may be 2, but is not limited thereto.
[0126] For example, the fluorescent dopant may be selected from the following compounds FD1 to FD22: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0127] Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto: [ka] [ka]
[0128] [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.
[0129] The electron transport region may include at least one layer selected from, but is not limited to, a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer (ETL), and an electron injection layer.
[0130] For example, the electron transport region may have a structure such as, but is not limited to, an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in this order from the light emitting layer.
[0131] An 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.
[0132] A "π-electron deficient nitrogen-containing ring" is a C ring having at least one *-N=*' moiety as a ring-forming moiety. 1 -C 60 It means a heterocyclic group.
[0133] For example, the "π-electron deficient nitrogen-containing ring" is i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' moiety are condensed with each other, or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups having at least one *-N=*' moiety and at least one C 5 -C 60 A heteropolycyclic group in which carbocyclic groups are condensed with each other may also be used.
[0134] Specific examples of the π-electron deficient nitrogen-containing ring include ring structures such as 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, but are not limited to these.
[0135] For example, the electron transport region may include a compound represented by formula 601 below. [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 601 In 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.
[0136] According to one embodiment, xe11 Ar 601 , and xe21 R 601 At least one of the above may contain a π-electron deficient nitrogen-containing ring as described above.
[0137] According to one embodiment, the ring Ar 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 , 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; 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 azine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole group, 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 may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0138] In the formula 601, if xe11 is 2 or more, 2 or more Ar 601 are also bonded to each other via a single bond.
[0139] According to another embodiment, the compound represented by formula 601 is Ar 601 may be anthracene.
[0140] According to yet another embodiment, the compound represented by 601 may be represented by the following formula 601-1: [ka] 601-1 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 ~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 independent 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 may be selected from the group consisting of alkoxy, phenyl, biphenylyl, terphenylyl and naphthyl groups.
[0141] According to one embodiment, in formulas 601 and 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, biphenyl group, terphenyl 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, benzocarbazo an aryl 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 hexa ... a sacenylene 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; may be selected from the group consisting of, but not limited to, azacarbazolylene group, benzoxazolylene group, isobenzoxazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group.
[0142] According to another embodiment, in formulae 601 and 601-1, xe1 and xe611 through xe613 may be 0, 1, or 2, independently of each other.
[0143] According to yet another embodiment, in formulas 601 and 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.
[0144] The electron transport region may include 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]
[0145] Alternatively, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ. [ka]
[0146] As yet another example, the electron transport region can use compounds such as, but not limited to, phosphine oxide-containing compounds, and according to one embodiment, the phosphine oxide-containing compounds are used in the hole blocking layer of the electron transport region, but are not limited to such compounds.
[0147] The thickness of the buffer layer, the hole blocking layer, or the electron control layer may be, independently of one another, 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.
[0148] The thickness of the electron transport layer may be 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, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.
[0149] 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.
[0150] 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 may be selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the metal ion of the alkaline earth metal complex may be 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 may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but are not limited thereto.
[0151] 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]
[0152] 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.
[0153] 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.
[0154] 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.
[0155] The alkali metal may be selected from Li, Na, K, Rb and Cs. According to one embodiment, the alkali metal may be Li, Na or Cs. According to another embodiment, the alkali metal may be Li or Cs, but is not limited thereto.
[0156] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0157] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0158] 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.
[0159] 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. According to one embodiment, the alkali metal compound is LiF, Li 2 It may be selected from among O, NaF, LiI, NaI, CsI, KI, but is not limited thereto.
[0160] The alkaline earth metal compound is BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1), Ba x Ca 1-x O(0 < x < 1), and may be selected from among such alkaline earth metal compounds. According to one embodiment, the alkaline earth metal compound may be selected from among BaO, SrO, and CaO, but is not limited thereto.
[0161] The rare earth metal compound is YbF 3 、ScF 3 、ScO 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 and TbF 3 and may be selected from among them. According to one embodiment, the rare earth metal compound is YbF 3 、ScF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3 and may be selected from among them, but is not limited thereto.
[0162] The above-mentioned alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes include ions of the above-mentioned alkali metals, alkaline earth metals and rare earth metals, and the ligands coordinated to the metal ions of the above-mentioned alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but are not limited thereto.
[0163] 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 composed of an organic substance.
[0164] 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, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
[0165] [Second electrode 190] The second electrode 190 is disposed on the organic layer 150. The second electrode 190 may be a cathode, which is an electron injecting electrode. In this case, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, each having a low work function.
[0166] 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 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0167] The second electrode 190 can have a single-layer structure having a single layer, or a multi-layer structure having multiple layers.
[0168] [Explanation of Figures 2 to 4] In addition, the organic light-emitting device 20 in FIG. 2 has a structure in which a first capping portion 210, a first electrode 110, an organic layer 150, and a second electrode 190 are stacked in order, the organic light-emitting device 30 in FIG. 3 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping portion 220 are stacked in order, and the organic light-emitting device 40 in FIG. 4 has a structure in which a first capping portion 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping portion 220 are stacked in order.
[0169] 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.
[0170] Light generated in the light-emitting layer in the organic layer 150 of the organic light-emitting element 20, 40 is extracted to the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping portion 210, and light generated in the light-emitting layer in the organic layer 150 of the organic light-emitting element 30, 40 is extracted to the outside through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping portion 220.
[0171] The first and second capping parts 210 and 220 improve the external light emission efficiency according to the principle of constructive interference.
[0172] The first capping part 210 and the second capping part 220 may be, independently of each other, an organic capping part made of an organic material, an inorganic capping part made of an inorganic material, or a composite capping part including an organic material and an inorganic material.
[0173] At least one of the first capping portion 210 and the second capping portion 220 may independently include at least one material selected from a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. The carbocyclic compound, the heterocyclic compound, and the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. According to an embodiment, at least one of the first capping portion 210 and the second capping portion 220 may independently include an amine-based compound.
[0174] According to another embodiment, at least one of the first capping portion 210 and the second capping portion 220 may include, independently of one another, a compound represented by Formula 201 or a compound represented by Formula 202.
[0175] According to yet another embodiment, at least one of the first capping portion 210 and the second capping portion 220 may, independently of each other, comprise a compound selected from the aforementioned compounds HT28 to HT33 and the following compounds CP1 to CP5, but is not limited thereto. [ka]
[0176] The organic light-emitting device has been described above with reference to FIGS. 1 to 4, but is not limited thereto.
[0177] Each layer included in the hole transport region, the light emitting layer, and the electron transport region can be 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) method.
[0178] 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 the vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., a deposition time of about 10 -8 Torr ~ approx. 10 -3 The vacuum level of torr and the deposition rate range of about 0.1 nm / sec to about 10 nm / sec may be selected in consideration of the material contained in the layer to be formed and the structure of the layer to be formed.
[0179] 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 the spin coating method, the coating conditions may be selected, for example, within a coating speed range of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature range of about 80°C to 200°C, taking into consideration the materials included in the layer to be formed and the structure of the layer to be formed.
[0180] [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.
[0181] In this specification, C 2 -C 60 The alkenyl group is 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 alkenyl.
[0182] In this specification, C 2 -C 60 The alkynyl group is 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.
[0183] In this specification, C 1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is C 1 -C 60 Specific examples of the aryl group include methoxy, ethoxy, and isopropyloxy groups.
[0184] 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 C 3 -C 10 It means a divalent group having the same structure as a cycloalkyl group.
[0185] 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.
[0186] In this specification, C 3 -C 10 The cycloalkenyl group is C 3 -C 10 It means a monovalent monocyclic group that has at least one double bond in the ring but does not have 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.
[0187] 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 10 Specific 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.
[0188] 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 more than one ring, the two or more rings are fused together.
[0189] In this specification, C 1 -C 60 The heteroaryl group contains at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom, and 1 -C 60 means a monovalent group having a heterocyclic aromatic system, C 1 -C 60 The heteroarylene group contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 -C 60 C 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 When the heteroaryl group and the C1-C60 heteroarylene group contain more than one ring, the two or more rings are fused together.
[0190] In this specification, C 6 -C 60 The aryloxy group is -OA. 102 (Here, A 102 is C 6 -C 60 aryl group), C 6 -C 60 The arylthio group is -SA 103 (Here, A 103 is C 6 -C 60 aryl group).
[0191] In the present specification, the monovalent 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-forming atoms are only carbon atoms, and the entire molecule is non-aromatic. Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. In the present specification, the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0192] In the present specification, the monovalent non-aromatic hetero-condensed polycyclic group means 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 hetero-condensed polycyclic group include a carbazolyl group. In the present specification, the divalent non-aromatic hetero-condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.
[0193] In this specification, C 4 -C 60 A carbocyclic group refers to a monocyclic or polycyclic group having 4 to 60 carbon atoms and containing only carbon as ring-forming atoms. 4 -C 60 A carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 4 -C 60 A carbocyclic group may be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. 4 -C 60 Depending on the number of substituents attached to the carbocyclic group, 4 -C 60 The carbocyclic group may be a trivalent or tetravalent group and may be subject to a variety of modifications.
[0194] In this specification, C 2 -C 60 Heterocyclic groups are C 4 -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 2 to 60 carbon atoms) as ring-forming atoms.
[0195] As used herein, the aforementioned substituted C 4 -C 60 Carbocyclic groups, substituted C 2 -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 -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 1 -C 60 At least one of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group is 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 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 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 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 21 )(Q 22 )(Q23), -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 and monovalent non-aromatic condensed heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q31)(Q 32 ), -C(=O)(Q 31 ), -S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ); 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 1 -C 60 C substituted with at least one selected from the group consisting of heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic heterocyclic condensed polycyclic groups, deuterium, -F and cyano groups 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 may be selected from aryl groups, biphenyl groups, and terphenyl groups.
[0196] 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.
[0197] 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 60 It belongs to the "substituted phenyl group" which is an "aryl group."
[0198] 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."
[0199] In this specification, unless otherwise defined, *, *' and *" refer to bonding sites between adjacent atoms in the chemical formula. EXAMPLES
[0200] The compound and the organic light-emitting device according to an 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.
[0201] [Synthesis example] Synthesis Example 1: Synthesis of Compound BD1 [ka]
[0202] Synthesis of intermediate compound [BD1-A] Iodobenzene (1.0eq), imidazole (1.2eq), CuI (0.01eq), K 2 CO 3 (2.0eq) and L-proline (0.02eq) were dissolved in dimethylsulfoanate (0.1M) and stirred at 160°C for 48 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 [BD1-A] (yield 65%).
[0203] Synthesis of intermediate compound [BD1-B] The intermediate compound [BD1-A] (2.0 eq) and diiodobutane (1.0 eq) were dissolved in toluene (1.0 eq) and stirred at 120°C for 12 hours. The reaction mixture was cooled to room temperature, and then filtered while washing with toluene to obtain a solid. The obtained solid was dried to synthesize the intermediate compound [BD1-B] (yield 59%).
[0204] Synthesis of intermediate compound [BD1-C] Intermediate compound [BD1-B] (1.0 eq), [Ir(COD)OMe] 2 (1.1eq), Ag 2 O (0.5eq) and sodium tert-butoxide (3.0eq) were dissolved in 2-ethoxyethanol (0.5M) and stirred at 120°C for 10 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 [BD1-C] (yield 21%).
[0205] Synthesis of intermediate compound [BD1-D] Intermediate compound [BD1-C] (1.0 eq) and silver triflate (1.2 eq) were dissolved in acetone (1.0 M) and stirred at room temperature for 4 hours. After removing most of the solvent from the reaction mixture under reduced pressure, acetonitrile (20 eq) was added and stirred for 0.5 hours. After removing the solvent under reduced pressure, the mixture was concentrated to synthesize intermediate compound [BD1-D] (yield 81%).
[0206] Synthesis of intermediate compound [BD1-E] 3-Bromopyrazine-2-amine (1.0eq), phenylboronic acid (1.2eq), K 2 CO 3 (2.0eq) and Pd(PPh 3 ) 4 (0.02eq) was dissolved in toluene (0.1M) and stirred at 120°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 organic layer was dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize intermediate compound [BD1-E] (yield 84%).
[0207] Synthesis of intermediate compound [BD1-F] The intermediate compound [BD1-E] (1.0 eq) was dissolved in ethanol (0.1 M), and 3-chlorobutan-2-one (1.1 eq) was slowly added dropwise thereto, followed by stirring at 80° C. for 24 hours.
[0208] After cooling the reaction mixture to room temperature, the mixture was extracted three times with dichloromethane and water to obtain an organic layer, which was then dried over magnesium sulfate, concentrated, and subjected to column chromatography to synthesize the intermediate compound [BD1-F] (yield 58%).
[0209] Synthesis of compound BD1 Intermediate compound [BD1-D], Intermediate compound [BD1-F], K 2 CO 3 (10.0eq) was dissolved in 2-ethoxyethanol (0.05M) and stirred at 120°C for 10 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 compound [BD1] (yield 61%).
[0210] 1 H NMR (400MHz, DMSO-d6): δ=8.82(d,1H), 8.61(d,1H), 8.33(d,1H), 7.54(m,3H), 7.23(m,4H), 6.77(m,2H), 6.67( m,2H), 5.21(d,2H), 5.06(d,2H), 3.17(m,2H), 3.01(m,2H), 2.55(s,3H), 2.23(s,3H), 1.53(m,2H), 1.50(m,2H) LCMS.Calcd for C 36 H 34 IrN 7 ([M]+):m / z 756.93.found:m / z 757.25
[0211] Synthesis Example 2: Synthesis of compound BD2 [ka]
[0212] Synthesis of intermediate compound [BD2-A] The intermediate compound [BD1-A] was synthesized in the same manner as the intermediate compound [BD1-A], except that dimethylimidazole was used instead of imidazole (yield 58%).
[0213] Synthesis of intermediate compound [BD2-B] The intermediate compound [BD1-B] was synthesized in the same manner as the intermediate compound [BD1-B], except that the intermediate compound [BD2-A] was used instead of the intermediate compound [BD1-A] (yield 51%).
[0214] Synthesis of intermediate compound [BD2-C] The intermediate compound [BD1-C] was synthesized in the same manner as the intermediate compound [BD1-C], except that the intermediate compound [BD2-B] was used instead of the intermediate compound [BD1-B] (yield 81%).
[0215] Synthesis of intermediate compound [BD2-D] The intermediate compound [BD1-D] was synthesized in the same manner as the intermediate compound [BD1-D] (yield 37%), except that the intermediate compound [BD2-C] was used instead of the intermediate compound [BD1-C].
[0216] Synthesis of compound BD2 The compound was synthesized in the same manner as compound [BD1], except that intermediate compound [BD2-D] was used instead of intermediate compound [BD1-D] (yield 64%).
[0217] 1 H NMR (400MHz, DMSO-d6): δ=8.82(d,1H), 8.61(d,1H), 8.33(d,1H), 7.54(m,3H), 7.23(m,4H), 6.77(m,2H), 6.67(m,2H), 3.17(m,2H), 3.01(m,2H), 2.55(s,3H), 2.36(s,12H), 2.23(s,3H), 1.53(m,2H), 1.50(m,2H) LCMS.Calcd for C 40 H 42 IrN 7 ([M]+):m / z 813.04found:m / z 813.31
[0218] Synthesis Example 3: Synthesis of compound BD3 [ka]
[0219] Synthesis of intermediate compound [BD3-A] The intermediate compound [BD1-A] was synthesized in the same manner as the intermediate compound [BD1-A], except that benzimidazole was used instead of imidazole (yield 55%).
[0220] Synthesis of intermediate compound [BD3-B] The intermediate compound [BD1-B] was synthesized in the same manner as the intermediate compound [BD1-B], except that the intermediate compound [BD3-A] was used instead of the intermediate compound [BD1-A] (yield 54%).
[0221] Synthesis of intermediate compound [BD3-C] The intermediate compound [BD1-C] was synthesized in the same manner as the intermediate compound [BD1-C], except that the intermediate compound [BD3-B] was used instead of the intermediate compound [BD1-B] (yield 74%). Synthesis of intermediate compound [BD3-D] The intermediate compound [BD1-D] was synthesized in the same manner as the intermediate compound [BD1-D] (yield 41%), except that the intermediate compound [BD3-C] was used instead of the intermediate compound [BD1-C].
[0222] Synthesis of compound BD3 The compound was synthesized in the same manner as compound [BD1], except that intermediate compound [BD3-D] was used instead of intermediate compound [BD1-D] (yield 61%).
[0223] 1 H NMR (400MHz, DMSO-d6): δ=8.82(d,1H), 8.61(d,1H), 8.33(d,1H), 7.54(m,3H), 7.23(m,4H), 7.00(d,1H), 6.90(m,1H) , 6.77(m,2H), 6.67(m,2H), 6.53(m,2H), 3.17(m,2H), 3.01(m,2H), 2.55(s,3H), 2.23(s,3H), 1.53(m,2H), 1.50(m,2H) Found: m / z 857.28
[0224] Example 1 Corning 15 Ω / cm SiO2 was used as the substrate and anode. 2 A glass substrate on which ITO (120 nm) was formed was cut to a size of 50 mm × 50 mm × 0.7 mm, and ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, and then irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning, and the glass substrate was then placed in a vacuum deposition apparatus.
[0225] 2-TNATA was vacuum-deposited on top of the ITO anode formed on the organic substrate to form a 60 nm-thick hole injection layer, and NPB was vacuum-deposited on top of the hole injection layer to form a 30 nm-thick hole transport layer.
[0226] On top of the hole transport layer, cohosts ETH1 and HTH1 (the weight ratio of ETH1 to HTH1 was 1:1) and a dopant compound BD1 were co-deposited so that the weight ratio of the cohost to the dopant was 90:10, to form a 30 nm-thick light-emitting layer.
[0227] Diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1) was evaporated on top of the light-emitting layer to form a 5 nm thick hole-blocking layer, Alq3 was evaporated on top of the hole-blocking layer to form a 30 nm thick electron-transporting layer, LiF was evaporated on top of the electron-transporting layer to form a 1 nm thick electron-injecting layer, and then Al was vacuum-evaporated on top of the electron-injecting layer to form a 300 nm thick cathode, thereby producing an organic light-emitting device. [ka] [ka]
[0228] Examples 2 to 5 and Comparative Examples 1 to 4 An organic light emitting device was prepared in the same manner as in Example 1, except that, in forming the light emitting layer, the compounds shown in Table 1 were used as the dopant instead of Compound 1.
[0229] Evaluation example 1 The driving voltage, current density, luminance, luminous efficiency, emitted light and maximum emission wavelength of the organic light-emitting devices fabricated in the above-mentioned Examples 1 to 5 and Comparative Examples 1 to 4 were measured using a Keithley SMU 236 and a luminance meter PR650. The results are shown in Table 1. [Table 1]
[0230] <Compound A> [ka] <Compound B> [ka] <Compound C> [ka] <Compound D> [ka]
[0231] Referring to Table 1, it was confirmed that the organic light-emitting devices of Examples 1 to 5 had a lower driving voltage and higher luminance, luminous efficiency, and life span than the organic light-emitting devices of Comparative Examples 1 to 4. [Explanation of symbols]
[0232] 10 Organic light-emitting device 110 1st electrode 150 Organic layer 190 2nd electrode 210 1st Capping Section 220 2nd Capping Section
Claims
1. An organometallic compound represented by the following chemical formula 1: M(L 1 ) n1 (L 2 ) n2 ・・・1 In the formula 1, M is selected from the group consisting of iridium (Ir), rhodium (Rh), cobalt (Co) and meitnerium (Mt); L 1 is a ligand represented by the following chemical formula 2-1, n1 is 1, 2 or 3, and when n1 is 2 or more, two or more L 1 are identical or different from each other, L 2 is a ligand represented by the following chemical formula 2-2 or 2-3, n2 is 0, 1 or 2, and when n2 is 2 or more, two or more L 2 are identical or different from each other, n1+n2 is 2 or 3; 【Chemistry 1】 ・・・2-1 In the above Chemical Formula 2-1, A 1 is selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene; X 1 ~X 4 are each independently C(R 2 ) and R 1 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 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -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 ), -P(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 ) (Q 2 ) is selected from R 2 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 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -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 ), -P(Q 1 ) (Q 2 ), -C(=O)(Q 1 ), -S(=O) 2 (Q 1 ), and -P(=O)(Q 1 ) (Q 2 ) is selected from b1 is selected from the group consisting of integers from 1 to 10; The above-mentioned substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl Groups, Substituted C 2 -C 60 Alkynyl Group, 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 -C 10 Heterocycloalkenyl Groups, Substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio group, substituted C 1 -C 60 At least one substituent of a group selected from a heteroaryl group, a substituted monovalent non-aromatic fused polycyclic group, and a substituted monovalent non-aromatic fused polycyclic heterocyclic group is 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 ), -P(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, 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 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 21 ) (Q 22 ) (Q 23 ), -N(Q 21 ) (Q 22 ), -B(Q 21 ) (Q 22 ), -P(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, 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 ), -P(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 3 , 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 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group; a C substituted with at least one selected from deuterium, -F and a cyano group; 1 -C 60 an alkyl group; a C substituted with at least one selected from the group consisting of deuterium, -F and a cyano group; 6 -C 60 an aryl group; or a biphenylyl group or a terphenylyl group, * is the binding site for M, 【Chemistry 4】 ・・・2-2 【Chemistry 5】 ・・・2-3 In the above Chemical Formula 2-2 or 2-3, X 21 and X 22 are each independently C(R 23 ) and X 23 and X 24 are each independently C(R 24 ) and A 11 ~A 14 , and A 21 and A 22 are, independently of one another, a ring structure selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, thiophene, furan, pyrrole, indole, indene, benzosilole, benzothiophene, benzofuran, carbazole, fluorene, dibenzosilole, dibenzothiophene, dibenzofuran, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline, 5,6,7,8-tetrahydroquinoline, and benzoquinazoline; b11 to b14, b21 to b22, and * refer to the explanations for b1 and * in Chemical Formula 1 above, respectively; In the above formulas 2-2 and 2-3, R 11 ~R 12 , and R 21 ~R 22 are each independently selected from the group consisting of hydrogen, -F, -Cl, -Br, -I, a methyl group, and an isopropyl group; R 13 ~R 16 , and R 25 ~R 26 are hydrogen, R 23 ~R 24 are each independently selected from hydrogen and a methyl group; n11 and n21 are each 4.
2. The organometallic compound of claim 1 , wherein n1 is 1 and n2 is 1 in Formula 1.
3. In the above formula 2-1, R 1 and R 2 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 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group and C 1 -C 20 Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl 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 C is substituted with at least one selected from 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group and C 1 -C 20 Alkoxy group; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, a zolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, A triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindo group, an alkyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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 pyridazin ... nyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, acridinyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl and imidazopyrimidinyl groups; and -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 ), -P(Q 1 ) (Q 2 ) and -P(=O)(Q 1 ) (Q 2 ); Q 1 ~Q 3 , and Q 31 ~Q 33 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 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 20 Aryl group, C 1 -C 20 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; C substituted with at least one selected from deuterium, -F and a cyano group 1 -C 20 Alkyl groups; C substituted with at least one selected from deuterium, -F and a cyano group 6 -C 20 Aryl groups; and 2. The organometallic compound of claim 1, wherein the aryl group is selected from the group consisting of a biphenyl group and a terphenyl group.
4. i) In the above formula 2-1, X 1 and X 2 is C(R 2 ) and R 2 is hydrogen, or ii) In the formula 2-1, X 3 and X 4 is C(R 2 ) and R 2 2. The organometallic compound according to claim 1, wherein is a methyl group, a t-butyl group, or an iso-propyl group.
5. Said L 1 is a ligand selected from the groups represented by the following chemical formulas 2-1(1) and 2-1(2): 【Chemistry 2】 ・・・2-1(1) 【Chemistry 3】 ・・・2-1(2) In the above chemical formulas 2-1(1) and 2-1(2), R 1a ~R 1d , and R 2a ~R 2d The explanation for R is given in claim 1. 1 and R 2 Please refer to the explanation of * denotes the binding site for M.
6. Said L 2 is a ligand selected from the groups represented by the following chemical formulas 2-2(1) to 2-2(3) and 2-3(1): 【Chemistry 6】 ・・・2-2(1) 【Chemistry 7】 ・・・2-2(2) 【Chemistry 8】 ・・・2-2(3) 【Chemistry 9】 ・・・2-3(1) In the above chemical formulas 2-2(1) to 2-2(3) and chemical formula 2-3(1), R 11a ~R 11d , R 12a ~R 12d , R 13a ~R 13d , R 14a ~R 14d , R 21a ~R 21d , R 22a ~R 22d , R 23a ~R 23b , and R 24a ~R 24b The explanation for R is given in claim 1. 11 ~R 16 , R 21 ~R 26 , n11 and n21, * denotes the binding site for M.
7. The organometallic compound according to claim 1, characterized in that the organometallic compound is selected from the following compounds BD1 to BD59: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】
8. 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; The light-emitting layer comprises one or more organometallic compounds according to any one of claims 1 to 7, the light-emitting layer further comprises one or more of a second compound and a third compound; the organometallic compound, the second compound, and the third compound are different from one another, When the light-emitting layer contains both a second compound and a third compound, the second compound and the third compound form an exciplex, The organic light-emitting device in which the organometallic compound and the second compound and / or the third compound do not form an exciplex.
9. The organic light emitting device according to claim 8 , wherein the second compound and the third compound form an exciplex, and the exciplex has an emission spectrum with a maximum emission wavelength of 390 nm or more and 500 nm or less.
10. The organic light emitting device according to claim 8, wherein an absolute value difference between a LUMO energy level of the organometallic compound and a LUMO energy level of the second compound or the third compound is 0.1 eV to 10 eV.
11. The organic light emitting device according to claim 8 , wherein an absolute value difference between a HOMO energy level of the organometallic compound and a HOMO energy level of the second compound or the third compound is 1.25 eV or less.
12. The second compound is represented by the following formula 3: The organic light emitting device according to claim 8 , wherein the third compound is represented by the following formula 4: 【Chemistry 16】 ・・・3 【Chemistry 17】 ・・・4 In the above formulas 3 and 4, X 31 is C(R 31 ) and N; X 32 is C(R 32 ) and N; X 33 is C(R 33 ) and N; X 34 is C(R 34 ) and N; X 35 is C(R 35 ) and N; X 36 is C(R 36 ) and N; X 31 ~X 36 At least one of is N; R 31 ~R 36 are each independently *-(L 31 ) a31 - (R 37 ) b37 a group represented by the formula (I), 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 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -C 60 Heteroaryl group, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 a heteroarylthio 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 ), -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 ), where R 31 ~R 36 At least one of the following is *-(L 31 ) a31 - (R 37 ) b37 is a group represented by L 31 is a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 heterocyclic groups, a31 is selected from the group consisting of integers from 0 to 6; R 37 is 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -C 60 Heteroaryl group, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 a heteroarylthio 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 ), -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 ) is selected from b37 is selected from the group consisting of integers from 1 to 10; A 41 and A 42 are, independently of each other, C 5 -C 60 Carbocyclic groups and C 1 -C 60 heterocyclic groups, X 41 is a single bond, O, S, B (R 43 ), N(R 43 ), C(R 43 ) (R 44 ) and Si(R 43 ) (R 44 ), and X 42 is a single bond, O, S, B (R 45 ), N(R 45 ), C(R 45 ) (R 46 ) and Si(R 45 ) (R 46 ), and X 41 and X 42 but at the same time not a single bond, R 41 ~R 42 are each independently *-(L 41 ) a41 - (R 47 ) b47 a group represented by the formula (I), 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 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -C 60 Heteroaryl group, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 a heteroarylthio 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 ), -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 ), where R 41 ~R 46 At least one of the following is *-(L 41 ) a41 - (R 47 ) b47 is a group represented by R 43 ~R 46 are each independently *-(L 41 ) a41 - (R 47 ) b47 a group represented by the formula (I), 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 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -C 60 Heteroaryl group, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 a heteroarylthio 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 ), -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 ), where R 41 ~R 46 At least one of the following is *-(L 41 ) a41 - (R 47 ) b47 is a group represented by L 41 is a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 heterocyclic groups, a41 is selected from the group consisting of integers from 0 to 6; R 47 is 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 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -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 1 -C 60 Heteroaryl group, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 a heteroarylthio 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 ), -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 ) is selected from b47 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 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, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 is selected from the group consisting of a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenylyl group, and a terphenylyl group; * indicates a bonding site with an adjacent atom.
13. The organic light emitting device according to claim 8, wherein the second compound is selected from the following ETH1 to ETH80, and the third compound is selected from the following HTH1 to HTH28: 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】
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