Organometallic compound, organic light-emitting device including the same, and electronic device including the organic light-emitting device

Abstract

To provide an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.SOLUTION: An organometallic compound is represented by Chemical Formula 1: M(L1)n1(L2)n2. In the Chemical Formula 1, for the explanations of M, L1, L2, n1, and n2, refer to the corresponding descriptions in the Specifications.SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present invention relates to an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device. [Background technology]

[0002] An organic light emitting device is a self-emitting device that has excellent characteristics such as viewing angle, response time, brightness, driving voltage, and response speed, and is capable of being made multicolored.

[0003] According to one example, an organic light emitting device includes an anode, a cathode, and an organic layer including an emitting layer disposed between the anode and the cathode. A hole transport region is provided between the anode and the emitting layer, and an electron transport region is provided between the emitting layer and the cathode. Holes injected from the anode move to the emitting layer via the hole transport region, and electrons injected from the cathode move to the emitting layer via the electron transport region. The holes and electrons recombine in the emitting layer region to generate excitons. Light is generated as the excitons change from an excited state to a ground state. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2017-39713 A Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention has been made in view of the above-mentioned conventional techniques, and an object of the present invention is to provide a novel organometallic compound, an organic light-emitting element using the same, and an electronic device including the organic light-emitting element. [Means for solving the problem]

[0006] In order to achieve the above object, an organometallic compound according to one embodiment of the present invention is represented by the following chemical formula 1. [C1] M(L 1 ) n1 (L 2 ) n2 In the above Chemical Formula 1, M is a transition metal; L 1 is a ligand represented by the following chemical formula 2: n1 is 1, 2, or 3; when n1 is 2 or more, 2 or more L 1 are the same or different from each other, L 2 is a monodentate, bidentate, tridentate, or tetradentate ligand; n2 is 0, 1, 2, 3, or 4; when n2 is 2 or more, 2 or more L 2 are the same or different from each other, L 1 and L 2 are different from each other, [ka] In the above Chemical Formula 2, A 21 or A 24 are each independently N or C; X 1 is O or S, L 13 is a single bond, at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 is a heterocyclic group, Ring CY 1 is C 5 -C 30 Carbocyclic group or C 1 -C 30 is a heterocyclic group, R 1 ~R 3 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, or -SF 5 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 1 -C 60 Alkylthio 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 group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, 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 group, substituted or unsubstituted C 1 -C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q 1 )(Q 2 ), -Si(Q 3 )(Q 4 )(Q 5 ), -Ge(Q 3 )(Q 4 )(Q 5 ), -B(Q 6 )(Q7 ), -P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ) and b1 is an integer from 0 to 20, b2 is an integer from 0 to 4, Multiple R 1 In the formula, two or more are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 Forming a heterocyclic group, In the plurality of R2, two or more are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 Forming a heterocyclic group, R 1 and R 2 are optionally linked together, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 Forming a heterocyclic group, R 10a For an explanation of 1 Please refer to the explanation on * and *' are binding sites with M in Chemical Formula 1, The substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C60 Alkoxy groups, substituted C 1 -C 60 Alkylthio 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 The heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituent of the substituted monovalent non-aromatic fused polycyclic heterocyclic group are each independently 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, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 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, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or any combination thereof, 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 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, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, 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, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or any combination thereof, substituted or unsubstituted, 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 -C60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or any combination thereof; Q 1 ~Q 9 , Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q 39 are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a deuterium, C 1 -C 60 Alkyl group, C 6 -C 60 aryl groups, or any combination thereof, substituted or unsubstituted 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 -C10 Heterocycloalkyl group; C 3 -C 10 Cycloalkenyl group; C 1 -C 10 Heterocycloalkenyl group; Deuterium, C 1 -C 60 Alkyl group, C 6 -C 60 aryl groups, or any combination thereof, substituted or unsubstituted C 6 -C 60 Aryl group; C 6 -C 60 Aryloxy group; C 6 -C 60 Arylthio group; C 1 -C 60 a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

[0007] According to another aspect, there is provided an organic light-emitting device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, the organic layer including one or more organometallic compounds represented by Chemical Formula 1.

[0008] The organometallic compound is contained in a light-emitting layer, and the organometallic compound contained in the light-emitting layer serves as a dopant.

[0009] In yet another aspect, there is provided an electronic device including the organic light emitting device. Effect of the Invention

[0010] The organometallic compounds of the present invention have excellent electrical properties, and electronic devices employing the organometallic compounds, such as organic light-emitting devices, have improved driving voltage, improved external quantum efficiency, and / or improved roll-off ratio. [Brief description of the drawings]

[0011] [Figure 1] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Specific examples of the embodiments of the present invention will be described in detail below.

[0013] The organometallic compound of the present invention is represented by the following Chemical Formula 1.

[0014] [C1] M(L 1 ) n1 (L 2 ) n2

[0015] In the above formula 1, M is a transition metal.

[0016] For example, M is a period 1 transition metal, a period 2 transition metal, or a period 3 transition metal.

[0017] As other examples, M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0018] According to one embodiment, M is Ir, Pt, Os, or Rh. In the above formula 1, L 1 is a ligand represented by the following chemical formula 2.

[0019] [ka]

[0020] For the explanation of Chemical Formula 2, please refer to the portions described in this specification.

[0021] In the above formula 1, n1 is L 1 n1 indicates the number of L 1are the same or different from each other. For example, n1 is 1 or 2.

[0022] In the above formula 1, L 2 is any organic ligand. For example, L 2 is a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand. 2 For the explanation of this, please refer to the parts described in this specification.

[0023] In the above formula 2, n2 is L 2 and is 0, 1, 2, 3, or 4. When n2 is 2 or more, two or more L2s are the same or different from each other. For example, n2 is 1 or 2.

[0024] In the above formula 1, L 1 and L 2 are different from each other.

[0025] According to one embodiment, in Formula 1, M is Ir or Os and n1+n2 is 3 or 4; or M is Pt and n1+n2 is 2.

[0026] According to another embodiment, in Formula 1, M is Ir; n1 and n2 are each independently 1 or 2; n1+n2 is 3.

[0027] According to yet another embodiment, in Formula 1, M is Ir; n1 is 3 and n2 is 0. Here, the three L 1 are identical to each other.

[0028] In the above formula 2, A 21 or A 24are each independently N or C. For example, A 21 or A 24 is C.

[0029] In the above formula 2, X 1 is O or S.

[0030] In the above formula 2, L 13 is a single bond, at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 It is a heterocyclic group.

[0031] For example, in the above formula 2, L 13 teeth, A single bond; or At least one R 10a a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group , a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isisoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group;

[0032] According to one embodiment, in Formula 2, L 13 teeth, A single bond; or At least one R 10a and n is a benzene group, a naphthalene group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group, each of which is substituted or unsubstituted by .

[0033] In the above formula 2, the ring CY 1 is C 5 -C 30 Carbocyclic group or C 1 -C 30 It is a heterocyclic group.

[0034] For example, in the above formula 2, the ring CY 1 is i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings and one or more second rings are fused to each other, the first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilol group, or a triazasilol group; The second ring is an adamantane group, a norbornane group (bicyclo[2.2.1]heptane group), a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0035] According to one embodiment, in Formula 2, the ring CY 1 is i) the first ring or ii) the second ring.

[0036] According to another embodiment, in Formula 2, the ring CY 1 is a fused ring in which two or more rings are fused together.

[0037] According to still another embodiment, in Formula 2, the ring CY 1 is iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings and one or more second rings are fused to each other.

[0038] According to one embodiment, in Formula 2, the ring CY 1is a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantane group, a norbornane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2] Octane group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, pyrrole group, borole group, phosphole group, cyclopentadiene group, silole group, germole group, thiophene group, selenophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermole group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzyl group, azabenzophosphole group, fluorene group, dibenzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, aza azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, azaborole group, azaphosphole group, azacyclopentadiene group, azasilole group, azagermole group, azaselenophene group, oxazole group, isisoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0039] According to another embodiment, in Formula 2, the ring CY 1 is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a quinazoline group, or a phenanthroline group.

[0040] In the above formula 2, R 1 ~R 3 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, or -SF 5 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 1 -C 60 Alkylthio 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 group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, 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 group, 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, -N(Q 1 )(Q 2 ), -Si(Q 3 )(Q 4 )(Q 5 ), -Ge(Q 3 )(Q 4 )(Q 5 ), -B(Q 6 )(Q 7 ), -P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ) Q 1 ~Q 9 For the explanation of this, please refer to the parts described in this specification.

[0041] For example, in the above formula 2, R 1 ~R 3 are each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl group, C 1 -C 20 Alkenyl group, C 1 -C 20 Alkoxy group or C 1 -C 20 Alkylthio 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, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantanyl groups, norbornanyl groups, norbornenyl groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, bicyclo[1.1.1]pentyl groups, bicyclo[2.1.1]hexyl groups, bicyclo[2.2.2]octyl groups, (C 1 -C 20 alkyl)cyclopentyl group, (C 1 -C 20 alkyl)cyclohexyl group, (C 1 -C 20 alkyl)cycloheptyl group, (C 1 -C 20 alkyl)cyclooctyl group, (C 1 -C 20 alkyl)adamantanyl group, (C 1 -C 20 alkyl)norbornanyl group, (C 1 -C 20 alkyl)norbornenyl group, (C 1 -C 20 alkyl)cyclopentenyl group, (C 1 -C 20 alkyl)cyclohexenyl group, (C 1 -C 20 alkyl)cycloheptenyl group, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl group, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl group, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C 1 -C 20 C substituted with an alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof; 1 -C 20 Alkyl group, C1 -C 20 Alkenyl group, C 1 -C 20 Alkoxy group or C 1 -C 20 Alkylthio 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, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 20 Alkyl groups, deuterated C 2 -C 20 Alkyl 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, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C 1 -C 20 alkyl)cyclopentyl group, (C 1 -C 20 alkyl)cyclohexyl group, (C 1 -C 20 alkyl)cycloheptyl group, (C 1 -C 20 alkyl)cyclooctyl group, (C 1 -C 20 alkyl)adamantanyl group, (C 1 -C 20 alkyl)norbornanyl group, (C 1 -C 20 alkyl)norbornenyl group, (C 1 -C 20 alkyl)cyclopentenyl group, (C 1 -C 20 alkyl)cyclohexenyl group, (C 1 -C20 alkyl)cycloheptenyl group, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl group, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl group, (C 1 -C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, terphenyl 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, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzo oxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or any combination thereof, substituted or unsubstituted, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20alkyl)phenyl group, biphenyl group, terphenyl 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, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinox a salinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl 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, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group; or -N(Q 1 )(Q 2 ), -Si(Q 3 )(Q 4 )(Q 5 ), -Ge(Q 3 )(Q 4 )(Q 5 ), -B(Q 6 )(Q 7 ), -P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ); and Q 1 ~Q 9 are each independently Deuterium, -F, -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CH 2 CH 3 , -CH 2 CD 3 , -CH 2 CD2 H, -CH 2 CDH 2 , -CHDCH 3 , -CHDCD 2 H, -CHDCDH 2 , -CHDCD 3 , -CD 2 CD 3 , -CD 2 CD 2 H, -C.D. 2 CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , -CH 2 CF 3 , -CH 2 CF 2 H, -CH 2 CFH 2 , -CHFCH 3 , -CHFCF 2 H, -CHFCFH 2 , -CHFCF 3 , -CF 2 CF 3 , -CF 2 CF 2 H or -CF 2 CFH 2 or Deuterium, -F, C 1 -C 10 an alkyl group, a phenyl group, or any combination thereof, substituted or unsubstituted, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl;

[0042] As another example, in the above formula 2, R 1 ~R 3 are each independently hydrogen, deuterium, -F, or -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2H, -CFH 2 , C 1 -C 10 Alkenyl group, C 2 -C 10 Alkenyl group, C 1 -C 10 Alkoxy group, C 1 -C 10 an alkylthio group, a group represented by one of the following chemical formulae 9-1 to 9-39, a group in which at least one hydrogen in the following chemical formulae 9-1 to 9-39 is replaced by deuterium, a group in which at least one hydrogen in the following chemical formulae 9-1 to 9-39 is replaced by -F, a group represented by one of the following chemical formulae 9-201 to 9-236, a group in which at least one hydrogen in the following chemical formulae 9-201 to 9-236 is replaced by deuterium, a group in which at least one hydrogen in the following chemical formulae 9-201 to 9-236 is replaced by -F, a group represented by one of the following chemical formulas 10-1 to 10-130, a group in which at least one hydrogen in the following chemical formulas 10-1 to 10-130 is replaced by deuterium, a group in which at least one hydrogen in the following chemical formulas 10-1 to 10-130 is replaced by -F, a group represented by one of the following chemical formulas 10-201 to 10-358, a group in which at least one hydrogen in the following chemical formulas 10-201 to 10-358 is replaced by deuterium, a group in which at least one hydrogen in the following chemical formulas 10-201 to 10-358 is replaced by -F, -Si(Q 3 )(Q 4 )(Q 5 ), or -Ge(Q 3 )(Q 4 )(Q 5 ) (However, Q 3 ~Q 5 The explanations for each of the above are referred to in the present specification.

[0043] [ka] [ka]

[0044] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0045] In the above chemical formulas 9-1 to 9-39, 9-201 to 9-236, 10-1 to 10-130, and 10-201 to 10-358, * is a bonding site with an adjacent atom, Ph is a phenyl group, and TMS and SiMe 3 is a trimethylsilyl group, and TMG and GeMe 3 is a trimethylgermyl group.

[0046] The above "groups in which at least one hydrogen in chemical formulae 9-1 to 9-39 is replaced with deuterium" and "groups in which at least one hydrogen in chemical formulae 9-201 to 9-236 is replaced with deuterium" are, for example, groups represented by the following chemical formulae 9-501 to 9-514 and 9-601 to 9-636.

[0047] [ka] [ka]

[0048] The above "groups in which at least one hydrogen atom in chemical formulae 9-1 to 9-39 is substituted with -F" and "groups in which at least one hydrogen atom in chemical formulae 9-201 to 9-236 is substituted with -F" are, for example, groups represented by the following chemical formulae 9-701 to 9-710.

[0049] [ka]

[0050] The above "groups in which at least one hydrogen in chemical formulas 10-1 to 10-130 has been replaced with deuterium" and "groups in which at least one hydrogen in chemical formulas 10-201 to 10-358 has been replaced with deuterium" are, for example, groups represented by the following chemical formulas 10-501 to 10-553.

[0051] [ka] [ka]

[0052] The above "groups in which at least one hydrogen atom in chemical formulae 10-1 to 10-130 is substituted with -F" and "groups in which at least one hydrogen atom in chemical formulae 10-201 to 10-358 is substituted with -F" are, for example, groups represented by the following chemical formulae 10-601 to 10-617.

[0053] [ka]

[0054] As yet another example, in the above formula 2, R 2 is hydrogen, deuterium, -F, cyano, substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, -Si(Q 3 )(Q 4 )(Q5 ), or -Ge(Q 3 )(Q 4 )(Q 5 ) or R 3 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 group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, 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 group, substituted or unsubstituted C 1 -C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0055] In the above formula 2, b1 is R 1 and is an integer from 0 to 20. When b1 is 2 or more, 2 or more R 1 are the same or different. For example, b1 is an integer of 0 to 10.

[0056] In the above formula 2, b2 is R 2 and is an integer from 0 to 4. When b2 is 2 or more, 2 or more R 2 are the same or different from each other. For example, b2 is 0, 1, or 2.

[0057] According to one embodiment, in Formula 2, [ka] The group represented by the following formulae 2(1) to 2(31) is represented by one of the following formulae 2(1) to 2(31).

[0058] [ka] [ka]

[0059] In the above chemical formulas 2(1) to 2(31), X 1 The explanation regarding is the same as that described in this specification, * is a binding site with M in the above Chemical Formula 1, *" is a bond site with an adjacent carbon atom.

[0060] According to another embodiment, in Formula 2, [ka] The group represented by the following formulae 2-1 to 2-57 is represented by one of them.

[0061] [ka] [ka] [ka]

[0062] In the above chemical formulas 2-1 to 2-57, X 1 The explanation regarding is the same as that described in this specification, R 11 ~R 16 The explanation regarding R 1 Although the explanation of R 11 ~R 16 Each of the is not hydrogen, * is a binding site with M in the above Chemical Formula 1, *" is a bond site with an adjacent carbon atom.

[0063] On the other hand, in the above chemical formula 1, L 2 is a bidentate ligand bonded to M in Chemical Formula 1 above via O, S, Se, N, C, P, Si, or As.

[0064] According to one embodiment, in Formula 1, L 2 is a bidentate ligand bonded to M in the above formula 1 via N and C, or a bidentate ligand bonded to M in the above formula 1 via two Os.

[0065] According to another embodiment, in Formula 1, L 2 is a group represented by one of the following chemical formulas 3A to 3F.

[0066] [ka]

[0067] In the above chemical formulas 3A to 3F, Y 13 is O, N, N(Z 1 ), P(Z 1 )(Z 2 ), or As(Z 1 )(Z 2 ) and Y 14 is O, N, N(Z 3 ), P(Z 3 )(Z 4 ), or As(Z 3 )(Z 4 ) and T 11 is a single bond, a double bond, *-C(Z 11 )(Z 12 )-*', *-C(Z 11 )=C(Z 12 )-*', *=C(Z 11 )-*', *-C(Z 11 )=*', *=C(Z 11)-C(Z 12 )=C(Z 13 )-*', *-C(Z 11 )=C(Z 12 )-C(Z 13 )=*',*-N(Z 11 )-*' or at least one Z 11 Substituted or unsubstituted C 5 -C 30 is a carbocyclic group, a11 is an integer from 1 to 10, and when a11 is 2 or more, T 11 are the same or different from each other, Y 11 and Y 12 are each independently C or N; T 21 is a single bond, a double bond, O, S, C(Z 11 )(Z 12 ), Si(Z 11 )(Z 12 ), or N(Z 11 ) and Ring CY 11 and CY 12 are each independently 5 -C 30 Carbocyclic group or C 1 -C 30 is a heterocyclic group, A 1 is P or As, Z 1 ~Z 4 , and Z 11 ~Z 13 The explanations for each are given in this specification as R 1 Please refer to the explanation on d1 and d2 are each independently an integer of 0 to 20; * and *' are respectively binding sites to M in Chemical Formula 1 above.

[0068] For example, the above chemical formula 3D [ka] is a group represented by one of the following chemical formulas CY11-1 to CY11-34, or The above chemical formulas 3C and 3D [ka] The group represented by the following formulas CY12-1 to CY12-34 is a group represented by one of the following formulas CY12-1 to CY12-34.

[0069] [ka]

[0070] [ka] [ka]

[0071] In the above chemical formulas CY11-1 to CY11-34 and the above chemical formulas CY12-1 to CY12-34, X 31 is S, N(Z 11 ), C(Z 11 )(Z 12 ), or Si(Z 11 )(Z 12 ) and X 41 is O, S, N(Z 21 ), C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ) and Y 11 , Y 12 , Z 1 , and Z 2 For the explanation of each of the above, please refer to the respective portions described in this specification. Z 11 ~Z 18 , and Z 21 ~Z 28 The explanations for each are given in this specification as R 1 Please refer to the explanation on d12 and d22 are each independently an integer of 0 to 2; d13 and d23 are each independently an integer of 0 to 3; d14 and d24 are each independently an integer of 0 to 4; d15 and d25 are each independently an integer of 0 to 5; d16 and d26 are each independently an integer of 0 to 6; In the above chemical formulae CY11-1 to CY11-34 and the above chemical formulae CY12-1 to CY12-34, * and *' respectively represent binding sites to M in the above chemical formula 1, and *" represents a binding site to an adjacent atom in the above chemical formula 3C, or a binding site to T21 in the above chemical formula 3D.

[0072] According to another embodiment, in Formula 1, L 2 is a ligand represented by the above formula 3D, in which Z 1 and Z 2 At least one of the following is independently selected from deuterium, -Si(Q 3 )(Q 4 )(Q 5 ), -Ge(Q 3 )(Q 4 )(Q 5 ), or C substituted with at least one deuterium 1 -C 60 It is an alkyl group.

[0073] According to yet another embodiment, in Formula 1, L 2 is a ligand represented by one of the following chemical formulas 3-1 and 3-101 to 3-112.

[0074] [ka]

[0075] [ka]

[0076] In the above chemical formula 3-1 and the above chemical formulas 3-101 to 3-112, Y 11 , Y 12 , Tamaki CY 12 , Z 1 ~Z 4 , Z 11 ~Z 13 For the explanation of d1, d2, and d3, please refer to the descriptions in this specification. Z 14 The description of Z 1 Please refer to the explanation on e2 is an integer from 0 to 2, e3 is an integer from 0 to 3, e4 is an integer from 0 to 4, * and *' are respectively binding sites to M in Chemical Formula 1 above.

[0077] For example, in the above formula 3-1, Y 11 is N and Y 12 is C.

[0078] As another example, in the above formula 3-1, Z 12 is -Si(Q 3 )(Q 4 )(Q 5 ), -Ge(Q 3 )(Q 4 )(Q 5 ), or C substituted with at least one deuterium 1 -C 60 It is an alkyl group.

[0079] As another example, in the above formula 3-1, Z 12 is -Si(Q 3 )(Q 4 )(Q 5 ) or -Ge(Q 3 )(Q 4 )(Q 5 ), and Z 13 is not hydrogen or a methyl group.

[0080] As yet another example, in the above formula 3-1, [ka] is a group represented by one of the following chemical formulas 3-1-1 to 3-1-16, or In the above formula 3-1, [ka] The group represented by the following formula 3-1(1) to 3-1(16) is a group represented by one of the following formulas 3-1(1) to 3-1(16).

[0081] [ka]

[0082] [ka]

[0083] In the above chemical formulas 3-1-1 to 3-1-16 and the above chemical formulas 3-1(1) to 3-1(16), Z 11 ~Z 14 For the explanation of 21 ~Z 24 The explanations for Z are given in this specification. 2 Although reference is made to the explanation of Z 11 ~Z 14 , and Z 21 ~Z 24 Each of the is not hydrogen, * and *' are binding sites with M in Chemical Formula 1 above, *" is a bond site with an adjacent atom.

[0084] In the above formula 2, i) a plurality of R 1 In the formula, two or more are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10aSubstituted or unsubstituted C 1 -C 30 ii) a plurality of R 2 In the formula, two or more are optionally linked together, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 forming a heterocyclic group; and iii) R 1 and R 2 are optionally linked together, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 It forms a heterocyclic group.

[0085] In this specification, R 10a The explanation regarding R 1 See the explanation regarding.

[0086] In the above Chemical Formula 2, * and *' are binding sites with M in the above Chemical Formula 1, respectively.

[0087] According to an embodiment, the organometallic compound represented by Formula 1 contains at least one deuterium.

[0088] For example, in the above formula 1, L 1 contains at least one deuterium.

[0089] As yet another example, in the above formula 1, n2 is not 0, L 2 contains at least one deuterium.

[0090] For example, the organometallic compound represented by the above chemical formula 1 is one of the following compounds 1 to 2023.

[0091]

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[0092] In the organometallic compound represented by the above chemical formula 1, L 1 is a ligand represented by the above formula 2, and L 1 The number n1 is 1, 2, or 3. That is, the organometallic compound is a ligand bound to a metal M, and necessarily includes at least one ligand represented by the above chemical formula 2.

[0093] In the ligand represented by the above chemical formula 2, ring A is a fused ring in which a 6-membered ring is fused to an imidazole ring, and ring B is X 1 A five-membered ring containing the ring CY 1 is a condensed ring in which A is condensed (see Chemical Formula 2A below). By including ring A having excellent stability and ring B having a long conjugation length, the stability of the organometallic compound represented by Chemical Formula 1 is improved, and the half-width of the emission peak of the PL (photoluminescence) spectrum and / or EL spectrum of the organometallic compound represented by Chemical Formula 1 is relatively small, and the life of an electronic device, for example, an organic light-emitting device, using the organometallic compound represented by Chemical Formula 1 is improved.

[0094] [ka]

[0095] In the organometallic compound represented by the above formula 1, the HOMO (highest occupied molecular orbital) energy level, the LUMO (lowest unoccupied molecular orbital) energy level, and S 1 Energy levels and T 1 The energy levels were evaluated using the Gaussian09 program with molecular structure optimization by density functional theory (DFT) based on B3LYP, and the results are shown in Table 1 below.

[0096] [Table 1]

[0097] From Table 1, it can be seen that the organometallic compound represented by Chemical Formula 1 has electrical properties suitable for use as a dopant in an electronic device, for example, an emitting layer of an organic light emitting device.

[0098] Those skilled in the art will be able to recognize how to synthesize the organometallic compound represented by the above Chemical Formula 1 by referring to the synthesis examples described below.

[0099] Therefore, the organometallic compound represented by Chemical Formula 1 is suitable for use as a dopant in an organic layer of an organic light-emitting device, for example, in an organic layer, an organic light-emitting device according to another aspect is provided, which comprises a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer comprises at least one organometallic compound represented by Chemical Formula 1.

[0100] The organic light-emitting device has an organic layer including the organometallic compound represented by Chemical Formula 1 as described above, and thus has a low driving voltage, a high external quantum efficiency, and a low roll-off ratio.

[0101] The organometallic compound represented by Chemical Formula 1 is used between a pair of electrodes of an organic light emitting device. For example, the organometallic compound represented by Chemical Formula 1 is included in an emission layer. Here, the organometallic compound acts as a dopant, and the emission layer further includes a host (i.e., the content of the organometallic compound represented by Chemical Formula 1 is less than the content of the host). The emission layer emits red or green light.

[0102] In this specification, "(the organic layer) contains one or more organometallic compounds" is interpreted as "(the organic layer) contains one organometallic compound belonging to the category of Chemical Formula 1 above, or two or more different organometallic compounds belonging to the category of Chemical Formula 1 above."

[0103] For example, the organic layer contains only the compound 1 as an organometallic compound. In this case, the compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer contains the compound 1 and the compound 2 as organometallic compounds. In this case, the compound 1 and the compound 2 are present in the same layer (for example, the compound 1 and the compound 2 are both present in the light-emitting layer).

[0104] The first electrode is an anode that is a hole-injection electrode and the second electrode is a cathode that is an electron-injection electrode, or the first electrode is a cathode that is an electron-injection electrode and the second electrode is an anode that is a hole-injection electrode.

[0105] For example, in an organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, where the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0106] In this specification, the term "organic layer" refers to a single and / or multiple layers disposed between a first electrode and a second electrode in an organic light-emitting device. The term "organic layer" includes not only organic compounds but also organometallic complexes containing metals.

[0107] Fig. 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, the structure and manufacturing method of the organic light emitting device according to an embodiment of the present invention will be described with reference to Fig. 1. The organic light emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are stacked in this order.

[0108] A substrate is additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a general organic light-emitting device can be used, but a glass substrate or a transparent plastic substrate that is excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is used.

[0109] The first electrode 11 is formed by providing a first electrode material on the upper part of the substrate using, for example, a deposition method or a sputtering method. The first electrode 11 is an anode. The first electrode material includes a material having a high work function so that holes can be easily injected. The first electrode 11 is a reflective electrode, a semi-transparent electrode, or a transparent electrode. Examples of the first electrode material include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) can be used.

[0110] The first electrode 11 has a single-layer structure or a multi-layer structure including two or more layers, for example, the first electrode 11 has a three-layer structure of ITO / Ag / ITO.

[0111] An organic layer 15 is disposed on top of the first electrode 11 .

[0112] Organic layers 15 include a hole transport region, an emissive layer, and an electron transport region.

[0113] The hole transport region is disposed between the first electrode 11 and the light emitting layer.

[0114] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0115] The hole transport region includes only a hole injection layer or only a hole transport layer, or has a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer stacked in this order from the first electrode 11.

[0116] When the hole transport region includes a hole injection layer, the hole injection layer is formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) method.

[0117] When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure of the hole injection layer, and the thermal properties. For example, the deposition temperature is about 100 to about 500° C., the vacuum degree is about 10 -8 ~about 10 -3 torr, and the deposition rate is selected from the range of about 0.01 to about 100 Å / sec.

[0118] When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the hole injection layer material, the target structure of the hole injection layer, and the thermal properties. The coating is performed at a coating speed of about 2,000 rpm to about 5,000 rpm, and the heat treatment temperature for removing the solvent after coating is selected from the temperature range of about 80°C to 200°C.

[0119] The conditions for forming the hole transport layer and the electron blocking layer are the same as those for forming the hole injection layer.

[0120] The hole transport region includes, for example, m-MTDATA, TDATA, 2-TNATA, NPB, 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 chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof.

[0121] [ka]

[0122] [ka] [ka]

[0123] In the above formula 201, Ar 101 and Ar 102 are each independently deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, 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 -C10 Cycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkyl groups, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, which are substituted or unsubstituted with a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof.

[0124] In the above formula 201, xa and xb are each independently an integer from 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is 0.

[0125] In the above chemical formulas 201 and 202, R 101 ~R 108 , R 111 ~R 119 , and R 121 ~R 124 are each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) or C 1 -C 10Alkoxy groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.); C substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, or any combination thereof 1 -C 10 Alkyl group or C 1 -C 10 an alkoxy group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl group, C 1 -C 10 alkoxy groups, or phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl groups, substituted or unsubstituted with any combination thereof.

[0126] In the above formula 201, R 109 stands for deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 20 Alkyl group, C 1 -C 20 The aryl group may be an alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, substituted or unsubstituted with any combination thereof.

[0127] According to an embodiment, the compound represented by Formula 201 is represented by Formula 201A below.

[0128] [ka]

[0129] In the above formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed description, see above.

[0130] For example, the hole transport region includes at least one of the following compounds HT1 to HT20.

[0131] [ka] [ka]

[0132] The thickness of the hole transport region is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or a combination thereof, the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer is about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-mentioned ranges, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage.

[0133] In addition to the materials described above, the hole transport region may further comprise a charge generating material to enhance electrical conductivity. The charge generating material may be dispersed uniformly or non-uniformly within the hole transport region.

[0134] The charge generating material is, for example, a p-dopant. The p-dopant is one of a quinone derivative, a metal oxide, and a cyano group-containing compound. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ), and F6-TCNNQ; metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compound HT-D1.

[0135] [ka]

[0136] The hole transport region further comprises a buffer layer.

[0137] The buffer layer compensates for the optical resonance distance according to the wavelength of light emitted from the light emitting layer, thereby increasing efficiency.

[0138] On the other hand, when the hole transport region includes an electron blocking layer, the material of the electron blocking layer includes a material used in the hole transport region as described above, a host material described later, or any combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP described later can be used as the material of the electron blocking layer.

[0139] The light-emitting layer is formed on the hole transport region by using a method such as vacuum deposition, spin coating, casting, LB method, etc. When the light-emitting layer is formed by the vacuum deposition and spin coating methods, the deposition and coating conditions vary depending on the compound used, and are generally selected from the same range of conditions as those for forming the hole injection layer.

[0140] The light-emitting layer includes a host and a dopant, and the dopant includes the organometallic compound represented by Chemical Formula 1 above.

[0141] The host includes TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, or any combination thereof.

[0142] [ka]

[0143] When the organic light emitting device 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 / or a blue light emitting layer, or the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

[0144] When the light emitting layer contains a host and a dopant, the content of the dopant is generally selected from the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host.

[0145] The dopant, as used herein, is an organometallic compound represented by the above Formula 1. For example, the dopant is a green phosphorescent dopant.

[0146] The thickness of the light-emitting layer is about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0147] An electron transport region is then placed on top of the light emitting layer.

[0148] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0149] For example, the electron transport region may have a structure of hole blocking layer / electron transport layer / electron injection layer, or electron transport layer / electron injection layer. The electron transport layer may have a single layer structure or a multilayer structure containing two or more different materials.

[0150] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region refer to the conditions for forming the hole injection layer.

[0151] When the electron transport region includes a hole blocking layer, the hole blocking layer can include, for example, BCP, BPhen, BAlq, or any combination thereof.

[0152] [ka]

[0153] The thickness of the hole blocking layer is about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking properties can be obtained without a substantial increase in driving voltage.

[0154] The electron transport layer includes BCP, BPhen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof.

[0155] [ka]

[0156] Alternatively, the electron transport layer contains at least one of the following compounds ET1 to ET25.

[0157] [ka] [ka]

[0158] The thickness of the electron transport layer is about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. 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.

[0159] The electron transport layer further comprises a metal-containing material in addition to the materials described above.

[0160] The metal-containing material includes a Li complex. The Li complex includes, for example, the following compound ET-D1 (LiQ) or the following compound ET-D2.

[0161] [ka]

[0162] The electron transport region also includes an electron injection layer that facilitates electron injection from second electrode 19 .

[0163] The electron injection layer is LiF, NaCl, CsF, Li 2 O, BaO, or any combination thereof.

[0164] The thickness of the electron injection layer is about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. 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] A second electrode 19 is disposed on the organic layer 15. The second electrode 19 is a cathode. The material for the second electrode 19 may be a metal, an alloy, an electrically conductive compound, or a combination thereof, each having a relatively low work function. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc., which are used as materials for forming the second electrode 19. Alternatively, various modifications are possible, such as forming a transmissive second electrode 19 using ITO or IZO to obtain a front light emitting element.

[0166] Although the organic light-emitting device has been described above with reference to FIG. 1, the present invention is not limited thereto.

[0167] In accordance with yet another aspect, there is provided an electronic device including the organic light emitting device, which can be used in a variety of applications, such as displays, lighting, and mobile phones.

[0168] In yet another aspect, there is provided a diagnostic composition comprising one or more organometallic compounds represented by Formula 1 above.

[0169] The organometallic compound represented by Chemical Formula 1 provides high luminescence efficiency, and therefore a diagnostic composition containing the organometallic compound has high diagnostic efficiency.

[0170] The diagnostic composition is used in a variety of applications, such as various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0171] In this specification, C 1 -C 60 The alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. 1 -C 60 The alkylene group is C 1 -C 60 It means a divalent group having the same structure as an alkyl group.

[0172] In this specification, C 1 -C 60 Alkyl group, C 1 -C 20 Alkyl group and / or C 1 -C 10Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. The alkyl groups may be substituted or unsubstituted, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl. For example, the above formula 9-33 is a branched C 6 It is an alkyl group and can be viewed as a tert-butyl group substituted with two methyl groups.

[0173] In this specification, C 1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is C 1 -C 60 (alkyl) means a univalent group having the chemical formula:

[0174] In this specification, C 1 -C 60 Alkoxy group, C 1 -C20 Alkoxy group or C 1 -C 10 Examples of alkoxy groups include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.

[0175] In this specification, C 2 -C 60 The alkenyl group is C 2 -C 60 It has a structure containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group. 2 -C 60 The alkenylene group is C 2 -C 60 It means a divalent group having the same structure as an alkenyl group.

[0176] In this specification, C 2 -C 60 The alkynyl group is C 2 -C 60 It has a structure containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group and a propynyl group. 2 -C 60 The alkynylene group is C 2 -C 60 It means a divalent group having the same structure as an alkynyl group.

[0177] In this specification, C 3 -C 10 Cycloalkyl groups are C 3 -C 10 means a monovalent saturated hydrocarbon monocyclic group, and in this specification, 3 -C 10 The cycloalkylene group is C 3 -C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0178] In this specification, C 3 -C 10Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like.

[0179] In this specification, C 1 -C 10 The heterocycloalkyl group is a C 1 -C 2 -O 1 -P 1 -Si 1 -Se 1 -Ge 1 -B 1 -S 1 -C 1 ... 1 -C 10 means a monovalent monocyclic group, and in this specification, C 1 -C 10 The heterocycloalkylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0180] In this specification, C 1 -C 10 Examples of heterocycloalkyl groups include silolanyl, silanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, and the like.

[0181] 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 carbon-carbon 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.

[0182] In this specification, C 1 -C10 The heterocycloalkenyl group is a C alkyl group containing at least one heteroatom selected from N, O, P, Si, Se, Ge, B, 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 heterocycloalkenyl groups include 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, and the like. 1 -C 10 The heterocycloalkenylene group is C 1 -C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.

[0183] In this specification, C 6 -C 60 Aryl group means a monovalent group having a C-C 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 the arylene group contains more than one ring, the two or more rings are fused together.

[0184] In this specification, C 7 -C 60 The alkylaryl group is a group having at least one C 1 -C 60 Alkyl-substituted C 6 -C 60 It means an aryl group.

[0185] In this specification, C 1 -C 60The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S as a ring-forming atom, and 1 -C 60 means a monovalent group having a cyclic aromatic system, C 1 -C 60 The heteroarylene group contains at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S as a ring-forming atom, and 1 -C 60 C means a divalent group having a carbocyclic aromatic system. 1 -C 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. 1 -C 60 Heteroaryl groups and C 1 -C 60 When a heteroarylene group contains more than one ring, the two or more rings are fused together.

[0186] In this specification, C 2 -C 60 The alkylheteroaryl group is a heteroaryl group having at least one C 1 -C 60 Alkyl-substituted C 1 -C 60 It means a heteroaryl group.

[0187] 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), C 1 -C 60 The alkylthio group is -SA 104 (Here, A 104is C 1 -C 60 (an alkyl group).

[0188] In the present specification, the monovalent non-aromatic condensed polycyclic group means 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 has non-aromaticity. 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 means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0189] In this 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 the ring-forming atoms include heteroatoms selected from N, O, P, Si, Se, Ge, B, and S, in addition to carbon, and the entire molecule has non-aromaticity. The monovalent non-aromatic hetero-condensed polycyclic group includes a carbazolyl group. In this 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.

[0190] In this specification, C 5 -C 30 A carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. 5 -C 30 A carbocyclic group is a monocyclic or polycyclic group. 10a (substituted or unsubstituted)C 5 -C 30 A "carbocyclic group" is, for example, a 10asubstituted or unsubstituted, adamantane, norbornane, norbornene, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, cyclopentane, cyclohexane, cyclohexene, benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, 1,2,3,4-tetrahydronaphthalene, cyclopentadiene, silole, fluorene, and the like.

[0191] In this specification, C 1 -C 30 The heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S, in addition to 1 to 30 carbon atoms as ring-forming atoms. 1 -C 30 The heterocyclic group is a monocyclic group or a polycyclic group. 10a (substituted or unsubstituted)C 1 -C 30 The "heterocyclic group" is, for example, (at least one R 10asubstituted or unsubstituted with, thiophene, furan, pyrrole, silole, borole, phosphole, selenophene, germole, benzothiophene, benzofuran, indole, indene, benzosilole, benzoborole, benzophosphole, benzoselenophene, benzogermole, dibenzothiophene, dibenzofuran, carbazole, dibenzosilole, dibenzoborole, dibenzophosphole, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene group, azadibenzofuran group, azabenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene group, azadibenzofuran group, aza A carbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, Examples of such groups include a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isisoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

[0192] As used herein, "deuterated C 1 -C 60 Alkyl group (or deuterated C 1 -C 20 Alkyl groups, deuterated C 2 -C 20 "C alkyl group, etc." refers to a C alkyl group substituted with at least one deuterium.1 -C 60 Alkyl group (or C substituted with at least one deuterium) 1 -C 20 Alkyl groups, C substituted with at least one deuterium 2 -C 20 For example, "deuterated C 1 The term "alkyl group (i.e., a deuterated methyl group)" refers to -CD 3 , -CD 2 H, and -CDH 2 Includes.

[0193] As used herein, "deuterated C 3 -C 10 "Cycloalkyl group" means a C substituted with at least one deuterium. 3 -C 10 The above "deuterated C 3 -C 10 For examples of the "cycloalkyl group", see, for example, Chemical Formula 10-501 above.

[0194] In this specification, "fluorinated C 1 -C 60 Alkyl group (or fluorinated C 1 -C 20 Alkyl groups, etc.), Fluorinated C 3 -C 10 "Cycloalkyl group", "Fluorinated C 1 -C 10 A "heterocycloalkyl group" and a "fluorinated phenyl group" are each a C substituted with at least one fluoro group (-F). 1 -C 60 Alkyl group (or C 1 -C 20 Alkyl groups, etc.), C 3 -C 10 Cycloalkyl groups, C 1 -C 10 It means a heterocycloalkyl group, and a phenyl group. For example, "fluorinated C 1 The term "alkyl group (i.e., a fluoromethyl group)" refers to -CF 3 , -CF 2 H, and -CFH2 The above "Fluoride C 1 -C 60 Alkyl group (or fluorinated C 1 -C 20 Alkyl groups, etc.), Fluorinated C 3 -C 10 Cycloalkyl group, or Fluorinated C 1 -C 10 The term "heterocycloalkyl group" refers to i) a fully fluorinated C group in which all hydrogen atoms in the group are replaced with fluoro groups. 1 -C 60 Alkyl group (or fully fluorinated C 1 -C 20 Alkyl groups, etc.), fully fluorinated C 3 -C 10 Cycloalkyl groups or fully fluorinated C 1 -C 10 or ii) a partially fluorinated C group in which not all hydrogen atoms in each group are replaced with fluoro groups. 1 -C 60 Alkyl group (or partially fluorinated C 1 -C 20 Alkyl groups, etc.), some fluorinated C 3 -C 10 Cycloalkyl group or partially fluorinated C 1 -C 10 It is a heterocycloalkyl group.

[0195] In this specification, "(C 1 -C 20 An "X" group is a group having at least one C 1 -C 20 It represents an "X" group substituted with an alkyl group. For example, in the present specification, "(C 1 -C 20 Alkyl)C 3 -C 10 "Cycloalkyl group" means a group having at least one C 1 -C 20 Alkyl-substituted C 3 -C 10 It indicates a cycloalkyl group, and "(C 1 -C 20"alkyl)phenyl group" means a group having at least one C 1 -C 20 This indicates a phenyl group substituted with an alkyl group. (C 1 An example of an alkyl)phenyl group is the toluyl group.

[0196] In this specification, "azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, and azadibenzothiophene 5,5-dioxide group" respectively mean or "an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene-5-oxide group, a 9H-fluoren-9-one group, or a dibenzothiophene-5,5-dioxide group," but in which at least one of the carbons forming the ring is replaced with nitrogen.

[0197] Replaced C 5 -C 30 Carbocyclic groups, substituted C 2 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60Alkoxy groups, substituted C 1 -C 60 Alkylthio 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 7 -C 60 Alkylaryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 Heteroaryl Groups, Substituted C 2 -C 60 The substituents of the alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused polycyclic group are each independently 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, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused polycyclic heterocyclic 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, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C2 -C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or any combination thereof, 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 7 -C 60 Alkylaryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 2 -C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused polycyclic heterocyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or any combination thereof;

[0198] In this specification, Q1 ~Q 9 , Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q 39 are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; a deuterium, C 1 -C 60 Alkyl group, C 6 -C 60 aryl groups, or any combination thereof, substituted or unsubstituted 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; Deuterium, C 1 -C 60 Alkyl group, C 6 -C 60 aryl groups, or any combination thereof, substituted or unsubstituted C 6 -C 60 Aryl group; C 6 -C 60 Aryloxy group; C 6 -C 60 Arylthio group; C 1 -C 60 a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

[0199] 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, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis examples, in the expression "'B' was used instead of 'A'", the amount of 'B' used and the amount of 'A' used are the same on a molar equivalent basis.

[0200] [Example]

[0201] <Synthesis Example 1 (Synthesis of Compound 1)>

[0202] [ka]

[0203] <Synthesis of Compound 1-2>

[0204] The compound 1-1 (10g, 35.33mmol) and iridium chloride (6.17g, 17.50mmol) were mixed with 90mL of ethoxyethanol and 30mL of distilled water, and the mixture was refluxed and stirred for 24 hours, and then cooled to room temperature. The solid product was separated by filtration, washed thoroughly with water / methanol / hexane in that order, and the solid product was dried in a vacuum oven to obtain 11.5g (83%) of compound 1-2.

[0205] <Synthesis of Compound 1-3>

[0206] Compound 1-2 (5.00 g, 3.16 mmol) was mixed with 45 mL of methylene chloride (MC), and then a mixture of AgOTf (1.70 g, 6.62 mmol) and 15 mL of methanol was added. After that, the mixture was stirred at room temperature for 18 hours while blocking light with aluminum foil, and then filtered through Celite to remove the solid formed. The filtrate was reduced in pressure to obtain a solid (compound 1-3), which was used in the next reaction without further purification.

[0207] <Synthesis of Compounds 1-4>

[0208] 2-Bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole) (10 g, 23.07 mmol), 4,4,5,5-tetramethyl-2-(5-methylbenzo[b]thiophen-3-yl)-1,3,2-dioxaborolane (6.33 g, 23.07 mmol), Pd(PPh 3 ) 4 (0.80 g, 0.69 mmol), and K 2 CO 3 (15.94 g, 117.27 mmol) was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water, and then refluxed and stirred for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride and anhydrous magnesium sulfate (MgSO 4 ) was added to remove moisture, and the residue obtained by filtering the filtrate under reduced pressure was purified by column chromatography under the condition of ethyl acetate (EA):hexane = 1:3 to obtain 10.51 g (91%) of compound 1-4.

[0209] <Synthesis of Compound 1>

[0210] Compound 1-3 (5.00 g, 5.15 mmol) and compound 1-4 (2.84 g, 5.67 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the reaction was carried out by refluxing and stirring at 120° C. for 18 hours, and then the temperature was lowered. The mixture obtained was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was carried out under EA:hexane=1:50 conditions to obtain compound 1 (2.20 g, 31%). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 70 H 79 IrN 4 SSi 2 :m / z 1256.5193, Found:1256.5198

[0211] <Synthesis Example 2 (Synthesis of Compound 2)>

[0212] [ka]

[0213] <Synthesis of Compound 2-4>

[0214] 2-Bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole) (10 g, 23.07 mmol), benzofuran-3-ylboronic acid (3.74 g, 23.07 mmol), Pd(PPh 3 ) 4 (0.80 g, 0.69 mmol), and K 2 CO 3 (15.94 g, 117.27 mmol) was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water, and then refluxed and stirred for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride and anhydrous magnesium sulfate (MgSO 4 ) was added to remove moisture, and the residue obtained by filtering the filtrate under reduced pressure was purified by column chromatography under conditions of EA:hexane=1:3 to obtain 8.69 g (80%) of compound 2-4.

[0215] <Synthesis of compound 2>

[0216] Compound 1-3 (3.00 g, 3.09 mmol) and compound 2-4 (1.60 g, 3.40 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the mixture was stirred under reflux at 120° C. for 18 hours to proceed with the reaction, and then the temperature was lowered. The mixture was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was performed under EA:hexane=1:50 conditions to obtain compound 2 (1.06 g, 28%). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 69 H 77 IrN 4 OSi 2 :m / z 1226.5265, Found:1226.5269

[0217] <Synthesis Example 3 (Synthesis of Compound 3)>

[0218] [ka]

[0219] <Synthesis of compound 3-4>

[0220] 2-Bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole) (5 g, 11.54 mmol), 5-phenylbenzothiophen-3-ylboronic acid (2.93 g, 11.54 mmol), Pd(PPh 3 ) 4 (0.40 g, 0.35 mmol), and K 2 CO 3 (7.97 g, 58.63 mmol) was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water, and the mixture was refluxed and stirred for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride and anhydrous magnesium sulfate (MgSO 4 ) was added to remove moisture, and the residue obtained by filtering the filtrate under reduced pressure was purified by column chromatography under conditions of EA:hexane=1:3 to obtain 5.46 g (84%) of compound 3-4.

[0221] <Synthesis of compound 3>

[0222] Compound 1-3 (2.20 g, 2.27 mmol) and compound 3-3 (1.41 g, 2.50 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the mixture was stirred under reflux at 120° C. for 18 hours to proceed with the reaction, and then the temperature was lowered. The mixture was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was performed under EA:hexane=1:50 conditions to obtain compound 3 (0.87 g, 29%). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 75 H 81 IrN 4 SSi 2 :m / z 1318.5350, Found:1318.5352

[0223] <Synthesis Example 4 (Synthesis of Compound 4)>

[0224] [ka]

[0225] <Synthesis of compound 4-4>

[0226] 2-Bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole) (6.32 g, 14.59 mmol), 2-(benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.80 g, 14.59 mmol), Pd(PPh 3 ) 4 (0.42 g, 0.36 mmol), and K 2 CO 3 (10.08 g, 72.95 mmol) was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water, and the mixture was refluxed and stirred for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride, and anhydrous magnesium sulfate (MgSO 4 ) was added to remove moisture, and the residue obtained by filtering the filtrate under reduced pressure was purified by column chromatography under conditions of EA:hexane=1:3 to obtain 5.33 g (75%) of compound 4-4.

[0227] <Synthesis of compound 4>

[0228] Compound 1-3 (1.50 g, 1.55 mmol) and compound 4-4 (0.75 g, 1.55 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the mixture was stirred under reflux at 120° C. for 18 hours to proceed with the reaction, and then the temperature was lowered. The mixture was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was performed under EA:hexane=1:50 conditions to obtain compound 4 (0.40 g, 21%). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 69 H 77 IrN 4 SSi 2 :m / z 1242.5037, Found:1242.5041

[0229] <Synthesis Example 5 (Synthesis of Compound 5)>

[0230] [ka]

[0231] <Synthesis of compound 5-4>

[0232] 2-Bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole) (3.00 g, 6.92 mmol), (5-methylbenzofuran-3-yl)boronic acid (1.22 g, 6.92 mmol), Pd(PPh 3 ) 4 (0.16 g, 0.14 mmol), and K 2 CO 3 (4.78 g, 34.60 mmol) was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water, and the mixture was refluxed and stirred for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride and anhydrous magnesium sulfate (MgSO 4) was added to remove moisture, and the residue obtained by filtering the filtrate under reduced pressure was purified by column chromatography under conditions of EA:hexane=1:3 to obtain 2.92 g (87%) of compound 5-4.

[0233] <Synthesis of compound 5>

[0234] Compound 1-3 (2.00 g, 2.06 mmol) and compound 5-4 (1.10 g, 2.27 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the mixture was stirred under reflux at 120° C. for 18 hours, and then the temperature was lowered. The mixture was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was performed under EA:hexane=1:50 conditions to obtain compound 5 (0.89 g, 35%). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 70 H 79 IrN 4 OSi 2 :m / z 1240.5422, Found:1240.5422

[0235] <Synthesis Example 6 (Synthesis of Compound 821)>

[0236] [ka]

[0237] <Synthesis of compound 821-2>

[0238] 5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridine (10g, 52.83mmol) and iridium chloride (8.47g, 24.01mmol) were mixed with 90mL of ethoxyethanol and 30mL of distilled water, and the mixture was stirred under reflux for 24 hours to react, after which the temperature was lowered to room temperature. The solid product was separated by filtration, and the solid obtained by washing thoroughly with water / methanol / hexane in that order was dried in a vacuum oven to obtain 12.04g (83%) of compound 821-2.

[0239] <Synthesis of compound 821-3>

[0240] After mixing 45 mL of MC with the above compound 821-2 (3.00 g, 2.48 mmol), AgOTf (1.40 g, 5.46 mmol) was dissolved in 15 mL of methanol and added. After that, the reaction was carried out by stirring at room temperature for 18 hours while blocking light with aluminum foil, and then the solid formed was removed by filtration through Celite, and the filtrate was depressurized to obtain a solid (compound 821-3), which was used in the next reaction without further purification.

[0241] <Synthesis of compound 812-4>

[0242] 2-Bromo-1-phenyl-1H-benzo[d]imidazole (3 g, 10.98 mmol), 4-naphtho[2,1-b]furan-1-ylboronic acid (2.33 g, 10.98 mmol), Pd(PPh 3 ) 4 (0.25 g, 0.22 mmol), and K 2 CO 3 (7.59 g, 54.90 mmol) was mixed with 80 mL of 1,4-dioxane and 40 mL of distilled water, and the mixture was refluxed and stirred for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride, and anhydrous magnesium sulfate (MgSO 4 ) was added to remove moisture, and the residue obtained by filtering the filtrate under reduced pressure was purified by column chromatography under conditions of EA:hexane=1:3 to obtain 2.57 g (65%) of compound 821-4.

[0243] <Synthesis of Compound 821>

[0244] Compound 821-3 (3 g, 2.56 mmol) and compound 821-4 (1.02 g, 2.82 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide, and the mixture was stirred under reflux at 120° C. for 18 hours, after which the temperature was lowered. The mixture was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was performed under EA:hexane=1:50 conditions to obtain compound 821 (0.74 g, 31%). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 51 H 27 D 12 IrN 4 O:m / z 928.3506, Found:928.3504

[0245] <Compound 7 (Synthesis of Compound 822)>

[0246] [ka]

[0247] <Synthesis of compound 822-2>

[0248] 2-Phenylpyridine (5g, 32.22mmol) and iridium chloride (5.17g, 14.65mmol) were mixed with 90mL of ethoxyethanol and 30mL of distilled water, and the mixture was stirred under reflux for 24 hours to react, after which the temperature was lowered to room temperature. The solid product was separated by filtration, washed thoroughly with water / methanol / hexane in that order, and the solid product was dried in a vacuum oven to obtain 5.50g (70%) of compound 822-2.

[0249] <Synthesis of compound 822-3>

[0250] After mixing 45 mL of MC with the above compound 822-2 (3.00 g, 2.80 mmol), AgOTf (1.29 g, 5.02 mmol) was dissolved in 15 mL of methanol and added. After that, the reaction was carried out by stirring at room temperature for 18 hours while blocking light with aluminum foil, and then the solid generated was removed by filtration through Celite. The filtrate was depressurized to obtain a solid (compound 822-3), which was used in the next reaction without further purification.

[0251] <Synthesis of Compound 822>

[0252] The compound 822-3 (2g, 2.80mmol) and compound 2-4 (1.45g, 3.08mmol) were mixed with 50mL of 2-ethoxyethanol and 50mL of N,N-dimethylformamide, and the mixture was stirred under reflux at 120°C for 18 hours, and then the temperature was lowered. The mixture was filtered, and the solid obtained was thoroughly washed with ethanol and hexane, and column chromatography was performed under EA:hexane = 1:50 conditions to obtain 0.54g (20%) of compound 822. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 55 H 45 IrN 4 O:m / z 970.3223, Found:970.3227

[0253] <Synthesis Example 8 (Synthesis of Compound 767)>

[0254] [ka]

[0255] <Synthesis of compound 767-2>

[0256] The compound 1-4 (5g, 9.99mmol) and iridium chloride (1.76g, 5.00mmol) were mixed with 90mL of ethoxyethanol and 30mL of distilled water, and the mixture was stirred under reflux for 24 hours to react, and then the temperature was lowered to room temperature. The solid product was separated by filtration, and the solid obtained by washing thoroughly with water / methanol / hexane in that order was dried in a vacuum oven to obtain 4.91g (80%) of compound 767-2.

[0257] <Synthesis of Compound 767>

[0258] The above compound 767-2 (4 g, 1.63 mmol), acetylacetone (1.80 g, 18 mmol), and K 2 CO 3 (2.49g, 18mmol) was added to 60ml of 2-ethoxyethanol and stirred at room temperature for 24 hours. The solid by-product was removed by filtration, and then chromatography was performed using EA / hexane conditions to obtain 0.63g (30% yield) of compound 767. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 73 H 71 IrN 4 O 2 S 2 :m / z 1292.4648, Found:1292.4644

[0259] Example 1

[0260] As an anode, a glass substrate on which ITO had been patterned was cut to a size of 50 mm × 50 mm × 0.5 mm, ultrasonically cleaned for 5 minutes using isopropyl alcohol and pure water, respectively, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes, and then placed in a vacuum deposition apparatus.

[0261] The following compounds HT3 and F6-TCNNQ were vacuum co-deposited on top of the anode in a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and the following compound HT3 was vacuum deposited on top of the hole injection layer to form a hole transport layer having a thickness of 1,650 Å.

[0262] Subsequently, the following compound CBP (host) and the above compound 1 (dopant) were co-deposited on the hole transport layer in a weight ratio of 95:5 to form a light emitting layer having a thickness of 400 Å.

[0263] Thereafter, the following compounds ET3 and ET-D1 were co-deposited in a volume ratio of 50:50 on top of the light-emitting layer to form a 350 Å-thick electron transport layer, the following ET-D1 was vacuum-deposited on top of the electron transport layer to form a 10 Å-thick electron injection layer, and Al was vacuum-deposited on top of the electron injection layer to form a 1,000 Å-thick cathode, thereby producing an organic light-emitting element.

[0264] [ka]

[0265] <Examples 2 to 7 and Comparative Example A>

[0266] An organic light emitting device was prepared in the same manner as in Example 1, except that the compounds shown in Table 2 were used as dopants instead of Compound 1 when forming the light emitting layer.

[0267] <Evaluation Example 1>

[0268] For each of the organic light-emitting devices manufactured in Examples 1 to 7 and Comparative Example A, the driving voltage (V), maximum external quantum efficiency (Max EQE, %), and roll-off ratio (%) were evaluated, and the results are shown in Table 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment. The roll-off ratio was calculated according to the following Equation 20. In Table 2, the maximum external quantum efficiency is shown as a relative value (%).

[0269] [Number 20] Roll-off ratio = {1-(efficiency (at 8,000nit) / maximum luminous efficiency)} x 100%

[0270] [Table 2]

[0271] [ka]

[0272] From Table 2 above, it can be seen that the organic light-emitting devices of Examples 1 to 7 have improved driving voltage, improved external quantum efficiency, and improved roll-off ratio characteristics compared to the organic light-emitting device of Comparative Example A.

[0273] Example 8 and Comparative Example B

[0274] An organic light emitting device was prepared in the same manner as in Example 1, except that, when forming the light emitting layer, the compounds shown in Table 3 were used as the dopant instead of Compound 1.

[0275] <Evaluation Example 2>

[0276] For each of the organic light-emitting devices manufactured in Example 8 and Comparative Example B, the driving voltage (V), maximum external quantum efficiency (Max EQE, %), and roll-off ratio (%) were evaluated using the same method as in Evaluation Example 1, and the results are shown in Table 3. In Table 3, the maximum external quantum efficiency is shown as a relative value (%).

[0277] [Table 3]

[0278] [ka]

[0279] From Table 3 above, it can be seen that the organic light emitting device of Example 8 has improved driving voltage, improved external quantum efficiency, and improved roll-off ratio compared to the organic light emitting device of Comparative Example B.

[0280] Although the embodiments of the present invention have been described in detail above, the present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the technical spirit of the present invention. [Explanation of symbols]

[0281] 10 Organic light-emitting device 11 1st electrode 15 Organic layer 19 2nd electrode

Claims

1. 1. An organometallic compound represented by the following chemical formula 1: [Chemical 1] M(L １ ) ｎ１ (L ２ ) ｎ２ In the above Chemical Formula 1, M is iridium; L １ is a ligand represented by the following chemical formula 2: n1 is 1, L2 is a ligand represented by the following chemical formula 3D: n2 is 2, and two L ２ are the same or different from each other, L １ and L ２ are different from each other, 【Chemistry 2】 【3D】 In Formulas 2 and 3D, A ２１ or A ２４ are each independently N or C; X １ is O or S, Y 11 and Y 12 are each independently C or N; T 21 is a single bond, a double bond, O, S, C(Z 11 )(Z 12 ), Si(Z 11 )(Z 12 ), or N(Z 11 ); d1 and d2 are each independently an integer from 0 to 20; L １３ is a single bond; or At least one R １０ａ a benzene group, a naphthalene group, a pyridine group, a dibenzofuran group, a dibenzothiophene group, or a carbazole group, each of which is substituted or unsubstituted by Ring CY １ ring CY 11 and ring CY 12 each independently represent a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a quinazoline group, or a phenanthroline group; R 1 , R 2 , Z 1 , Z 2 , Z 11 and Z 12 are each independently hydrogen, deuterium, —F, a cyano group, a substituted or unsubstituted C １ -C ６０ Alkyl group, substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C １ -C １０ Heterocycloalkyl group, substituted or unsubstituted C ６ -C ６０ Aryl 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, -N(Q １ ) (Q ２ ), -Si(Q ３ ) (Q ４ ) (Q ５ ), or -Ge(Q ３ ) (Q ４ ) (Q ５ ) and R 3 is deuterium, -F, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 1 -C 60 heteroaryl group; b1 is an integer from 0 to 20, b2 is an integer from 0 to 4, Multiple R １ In the formula, two or more are optionally linked to each other, and at least one R １０ａ C substituted or unsubstituted ５ -C ３０ a carbocyclic group, or at least one R １０ａ C substituted or unsubstituted １ -C ３０ Forming a heterocyclic group, Multiple R ２ In the formula, two or more are optionally linked to each other, and at least one R １０ａ C substituted or unsubstituted ５ -C ３０ a carbocyclic group, or at least one R １０ａ C substituted or unsubstituted １ -C ３０ Forming a heterocyclic group, R １ and R ２ are optionally linked to each other, and at least one R １０ａ C substituted or unsubstituted ５ -C ３０ a carbocyclic group, or at least one R １０ａ C substituted or unsubstituted １ -C ３０ Forming a heterocyclic group, R １０ａ The explanation regarding R １ Please refer to the explanation on * and *' are binding sites with M in Chemical Formula 1, The substituted C １ -C ６０ Alkyl groups, substituted C ３ -C １０ Cycloalkyl groups, substituted C １ -C １０ Heterocycloalkyl groups, substituted C ６ -C ６０ The substituents of the aryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group are each independently 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, or C １ -C ６０ 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, -N(Q １１ ) (Q １２ ), -Si(Q １３ ) (Q １４ ) (Q １５ ), -Ge(Q １３ ) (Q １４ ) (Q １５ ), -B(Q １６ ) (Q １７ ), -P(=O)(Q １８ ) (Q １９ ), -P(Q １８ ) (Q １９ ), or any combination thereof; １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, or C １ -C ６０ 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, -N(Q ２１ ) (Q ２２ ), -Si(Q ２３ ) (Q ２４ ) (Q ２５ ), -Ge(Q ２３ ) (Q ２４ ) (Q ２５ ), -B(Q ２６ ) (Q ２７ ), -P(=O)(Q ２８ ) (Q ２９ ), -P(Q ２８ ) (Q ２９ ), or any combination thereof, substituted or unsubstituted, ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; -N(Q ３１ ) (Q ３２ ), -Si(Q ３３ ) (Q ３４ ) (Q ３５ ), -Ge(Q ３３ ) (Q ３４ ) (Q ３５ ), -B(Q ３６ ) (Q ３７ ), -P(=O)(Q ３８ ) (Q ３９ ), or -P(Q ３８ ) (Q ３９ ); or any combination thereof; Q １ ~ Q 5, Q １１ ~Q １９ , Q ２１ ~Q ２９ , and Q ３１ ~Q ３９ teeth, Each independently represents hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; deuterium, C １ -C ６０ Alkyl group, C ６ -C ６０ aryl groups, or any combination thereof, substituted or unsubstituted 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; deuterium, C １ -C ６０ Alkyl group, C ６ -C ６０ aryl groups, or any combination thereof, substituted or unsubstituted C ６ -C ６０ Aryl group; C ６ -C ６０ Aryloxy group; C ６ -C ６０ Arylthio group; C １ -C ６０ a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

2. R ２ is hydrogen, deuterium, -F, a cyano group, a substituted or unsubstituted C １ -C ６０ Alkyl group, substituted or unsubstituted C ３ -C １０ Cycloalkyl group, -Si(Q ３ ) (Q ４ ) (Q ５ ), or -Ge(Q ３ ) (Q ４ ) (Q ５ ) and R ３ is a substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C １ -C １０ Heterocycloalkyl group, substituted or unsubstituted C ６ -C ６０ An aryl group, or a substituted or unsubstituted C １ -C ６０ 2. The organometallic compound of claim 1, which is a heteroaryl group.

3. In the above Chemical Formula 2, 【Chemistry 2-CY1】 The organometallic compound according to claim 1, characterized in that the group represented by the formula: 【Chemistry 2(1)-2(23)】 【Chemistry 2(24)-2(31)】 In the above chemical formulas 2(1) to 2(31), X １ The explanation regarding is the same as that described in claim 1, * is a binding site with M in Chemical Formula 1; *" is a bonding site with an adjacent carbon atom.

4. In the above Chemical Formula 2, 【Chemistry 2-CY1a】 The organometallic compound according to claim 1, characterized in that the group represented by the formula: 【Chemistry (2-1)-(2-24)】 【Chemistry (2-25)-(2-42)】 【Chemistry (2-43)-(2-57)】 In the chemical formulas 2-1 to 2-57, X １ The explanation regarding is the same as that described in claim 1, R １１ ~R １６ The explanation regarding R １ Although reference is made to the description of R １１ ~R １６ Each of the is not hydrogen, * is a binding site with M in Chemical Formula 1; *" is a bonding site with an adjacent carbon atom.

5. Said L ２ is a ligand represented by the above formula 3D, In the above formula 3D, Z １ and Z ２ At least one of the following is independently selected from deuterium, -Si(Q ３ ) (Q ４ ) (Q ５ ), -Ge(Q ３ ) (Q ４ ) (Q ５ ), or C substituted with at least one deuterium １ -C ６０ 2. The organometallic compound according to claim 1, which is an alkyl group.

6. 2. The organometallic compound according to claim 1, wherein L2 is a ligand represented by the following formula 3-1: 【Chemistry 3-1】 In the above Chemical Formula 3-1, Y １１ , Y １２ , Tamaki CY １２ For the explanation of Z 2 and d2, please refer to the description in claim 1. Z 11 to Z １４ The explanation for each of the above is given in claim 1. １ Please refer to the explanation on * and *' are binding sites with M in Chemical Formula 1, respectively.

7. In the above formula 3-1, Z １２ is -Si(Q ３ ) (Q ４ ) (Q ５ ), -Ge(Q ３ ) (Q ４ ) (Q ５ ), or C substituted with at least one deuterium １ -C ６０ 7. The organometallic compound according to claim 6, which is an alkyl group.

8. In the above formula 3-1, Z １２ is -Si(Q ３ ) (Q ４ ) (Q ５ ) or -Ge(Q ３ ) (Q ４ ) (Q ５ ) and Z １３ 7. The organometallic compound of claim 6, wherein is not hydrogen or a methyl group.

9. In the above Chemical Formula 3-1, 【Chemistry (3-1)-Y11】 is a group represented by one of the following chemical formulas 3-1-1 to 3-1-16: In the above Chemical Formula 3-1, 【Chemical (3-1)-CY12】 The organometallic compound according to claim 6, characterized in that the group represented by the formula: is a group represented by one of the following chemical formulas 3-1(1) to 3-1(16). 【Chemistry (3-1-1) - (3-1-16)】 【(3-1(1))-(3-1(16))】 In the chemical formulas 3-1-1 to 3-1-16 and the chemical formulas 3-1(1) to 3-1(16), Z １１ ~Z １４ For the explanation of ２１ ~Z ２４ The explanation for each of the above is given in claim 6. ２ Although reference is made to the description of Z １１ ~Z １４ , and Z ２１ ~Z ２４ Each of the is not hydrogen, * and *' are binding sites with M in Chemical Formula 1, *" is a bonding site with an adjacent atom.

10. 2. The organometallic compound of claim 1, which contains at least one deuterium.

11. A first electrode; A second electrode; an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; The organic light-emitting device according to claim 1 , wherein the organic layer comprises at least one organometallic compound.

12. the first electrode is an anode; the second electrode is a cathode; the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode; the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof; 12. The organic light emitting device of claim 11, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

13. The organic light-emitting device according to claim 11 , wherein the organometallic compound is contained in the light-emitting layer.

14. An electronic device comprising the organic light-emitting element according to claim 11 .

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