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: The organometallic compound is represented by the chemical formula 1: M(L1)n1(L2)n2, where M, L1, L2, n1 and n2 are as described in the specification.SELECTED DRAWING: Figure 1

Description

[Technical field]

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

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

[0003] According to one example, an organic light emitting device has 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 ...(chemical formula 1) In the above Chemical Formula 1, M is Ir; L 1 is a ligand represented by the following chemical formula 2: L 2 is a ligand represented by the following chemical formula 3: n1 and n2 are each independently 1 or 2; The sum of n1 and n2 is 3. , if n1 is 2, then 2 L 1 are the same or different from each other, and when n2 is 2, two L 2 are the same or different from each other, [ka] [ka] In the above Chemical Formulas 2 and 3, Y 21 teeth, In C can be, Ring CY 2 teeth , a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a benzene group condensed with a norbornane group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group. and X 11 is Si or Ge, X 1 O or S in can be, A 11 Or A 14 are each independently C or N, but A 11 Or A 14 One of the formulas is [ka] C bonded to a group represented by the formula 11 Or A 14one of which is C bound to M in Formula 1; A 15 Or A 18 , and A 21 Or A 24 are each independently C or N; A 11 Or A 18 At least one of is N; L 3 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, R 14 Or R 16 are each independently deuterium, -F, a cyano group, or C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl groups, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 C substituted or unsubstituted with alkyl)phenyl, naphthyl, pyridinyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof; 1 -C 20 Alkyl group, C 3 -C 10 a cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; R 2 , R 11 Or R 13 , and Z 1 Or Z 3 teeth , each independently hydrogen, deuterium, -F , S Ano group , placed Substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl group , placed 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 group , placed 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 groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -Si(Q 3 )(Q 4 )(Q 5 ), or -Ge(Q 3 )(Q 4 )(Q 5 )in can be, a2 is 0~ 10 If a2 is 2 or more, R 2 are the same or different from each other, b1 is an integer of 0 to 5, and when b1 is 2 or more, Z 1 are the same or different from each other, b2 is an integer of 0 to 4, and when b2 is 2 or more, 2 or more Z2 are the same or different from each other, R 11 and R 12 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, Multiple R 2 Two or more of the 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, Multiple Zs 1 Two or more of the 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, Multiple Zs 2 Two or more of the 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 Z 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 60Alkenyl base, place Replaced C 1 -C 60 Alkoxy groups, substituted C 1 -C 60 Alkylthio groups, substituted C 3 -C 10 Cycloalkyl group , placed Replaced 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 substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are Deuterium, -F 、- CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , S Ano group 、C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group 、C 1 -C 60 Alkoxy group or C 1 -C 60 Alkylthio groups; Deuterium, -F 、- CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , S Ano group 、C 3 -C 10 Cycloalkyl group 、C 6 -C 60 Aryl Group ,also is replaced by any combination of them, C 1 -C 60Alkyl group, C 2 -C 60 Alkenyl group 、C 1 -C 60 Alkoxy group or C 1 -C 60 Alkylthio groups; Deuterium, -F 、- CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , S Ano group 、C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group 、C 1 -C 60 Alkoxy group, C 1 -C 60 Alkylthio group, C 3 -C 10 Cycloalkyl 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 ,also is any combination thereof, substituted or unsubstituted, C 3 -C 10 Cycloalkyl 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, or monovalent non-aromatic condensed heteropolycyclic group ; - Si(Q 33 )(Q34 )(Q 35 ), or -Ge(Q 33 )(Q 34 )(Q 35 ); or any combination thereof; The above Q 3 Or Q 5 , and Beauty Q 33 Or Q 35 are each independently Hydrogen; Deuterium; -F ; Ano group ; heavy Hydrogen, -F ,also or any combination thereof, substituted or unsubstituted C1-C60 alkyl groups. or Deuterium, -F, C 1 -C 60 Alkyl groups, or C 6 -C 60 Aryl Base; It is.

[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 of the organometallic compounds.

[0008] The organometallic compound is included in a light-emitting layer, and the organometallic compound included 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 compound of the present invention has excellent thermal stability and / or electrical properties, and an electronic device using the organometallic compound, such as an organic light-emitting device, has improved external quantum efficiency and improved life characteristics, and high-quality electronic devices can be produced by using the organic light-emitting device of the present invention. [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.

[0019] In the above formula 1, L 1 is a ligand represented by the following chemical formula 2, and L 2is a ligand represented by the following chemical formula 3.

[0020] [ka]

[0021] [ka]

[0022] For the explanation of the above chemical formulas 2 and 3, please refer to the parts described in this specification.

[0023] In the above formula 1, L 1 and L 2 are different from each other.

[0024] In the above formula 1, n1 and n2 are each L 1 and L 2 and each independently is 1 or 2. When n1 is 2, two L 1 are the same or different from each other, and when n2 is 2, two L 2 are the same or different from each other.

[0025] For example, in the above formula 1, i) n1 is 2 and n2 is 1, or ii) n1 is 1 and n2 is 2.

[0026] According to an embodiment, in Formula 1, i) M is Ir or Os, and n1+n2 is 3 or 4, or ii) M is Pt, and n1+n2 is 2.

[0027] In the above formula 2, Y 21 is C or N.

[0028] For example, Y 21 is C.

[0029] In the above formula 2, the ring CY 2 is C 5 -C30 Carbocyclic group or C 1 -C 30 It is a heterocyclic group.

[0030] For example, the ring CY 2 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, a germole group, a borole group, a selenophene group, a phosphole group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, an azagermole group, an azaborole group, an azaselenophene group, or an azaphosphole 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.

[0031] According to one embodiment, the ring CY 2is a cyclopentene group, a cyclohexane group, a cyclohexene group, 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 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, 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 dibenzo Phosphole 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, 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, quinoxaline group, quinazoline group, phenanthroline group, a phenylene group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole 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, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0032] According to one embodiment, the ring CY 2is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a 1,2,3,4-tetrahydronaphthalene group, an indole group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an azabenzosilole group, a pyridine group, a benzimidazole group, a benzoxazole group, or a benzothiazole group.

[0033] In another embodiment, the ring CY 2 is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a 1,2,3,4-tetrahydronaphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group.

[0034] In the above formula 2, X 11 is Si or Ge.

[0035] In the above formula 3, X 1 is O, S, Se, N(Z 19 ), C(Z 19 )(Z 20 ), or Si(Z 19 )(Z 20 ) Z 19 and Z 20 For the explanation of this, please refer to the parts described in this specification.

[0036] For example, X 1 is O, S, or N(Z 19 ).

[0037] In the above formula 3, A 11 Or A 14 are each independently C or N, but A 11 Or A 14 One of the formulas is [ka] C bonded to a group represented by the formula 11 Or A 14 One of them is C bound to M in the above formula 1.

[0038] In the above formula 3, A 15 Or A 18 , and A 21 Or A 24 are each independently C or N.

[0039] In the above formula 3, A 11 Or A 18 At least one of is N.

[0040] For example, A in the above formula 3 11 Or A 18 In the above, one or two are N.

[0041] According to one embodiment, A of Formula 3 13 Or A 18 In the above, one or two are N.

[0042] According to another embodiment, A of Formula 3 15 Or A 18 In the above, one or two are N.

[0043] According to still another embodiment, in the above formula 3, A 18 is N.

[0044] According to still another embodiment, in the above formula 3, A 21 Or A 24 are both C.

[0045] According to still another embodiment, in the above formula 3, A 21 Or A 24 At least one of (e.g., A 21 Or A 24 In the above, 1 or 2) is N.

[0046] In the above formula 3, L 3 is a single bond, at least one R 10a Substituted or unsubstituted C 5 -C 30A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 It is a heterocyclic group.

[0047] For example, L 3 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 isoxazole 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;

[0048] According to one embodiment, in Formula 3, L 3 teeth, A single bond; or At least one R 10a a substituted or unsubstituted benzene group;

[0049] According to another embodiment, in Formula 3, L 3 teeth, A single bond; or Deuterium, -F, cyano group, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl groups, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 a benzene, naphthalene, dibenzofuran, or dibenzothiophene group, substituted or unsubstituted with an alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;

[0050] In the above formulas 2 and 3, R 2 , R 11 Or R 16 , and Z 1 Or Z 3 , Z 19 , and Z 20 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 10Cycloalkyl 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 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 ) The above Q 1 Or Q 9 For the explanation of each, please refer to the respective parts described in this specification.

[0051] For example, R 2 , Z 1 , and Z 2 Each of is not hydrogen. For example, in formulas 2 and 3 above, R 2 , R 11 Or R 16 , and Z 1 Or Z3 , Z 19 , and Z 20 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 or C 1 -C 20 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, 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 1 -C 20 Alkyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantanyl groups, norbornanyl groups (bicyclo[2.2.1]heptyl 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 20alkyl)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 1,2,3,4-tetrahydronaphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof; 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, 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 1 -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 20alkyl)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 20alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl 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, benzo Quinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), 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, 1,2,3,4-tetrahydronaphthyl 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, benzo a quinolinyl group, a quinoxalinyl 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 Or Q 9 are each independently -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CH 2 CH 3 , -CH 2 CD 3 , -CH2 CD 2 H, -CH 2 CDH 2 , -CHDCH 3 , -CHDCD 2 H, -CHDCDH 2 , -CHDCD 3 , -CD 2 CD 3 , -CD 2 CD 2 H or -CD 2 CDH 2 or Deuterium, C 1 -C 20 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;

[0052] According to another embodiment, in Formulas 2 and 3, R 2 , R 11 Or R 13 , and Z 1 Or Z 3 , Z 19 , and Z 20 are each independently Hydrogen, deuterium, -F, or a cyano group; or Deuterium, -F, cyano group, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl groups, (C 1 -C 20 Alkyl)C 3 -C10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 C substituted or unsubstituted with alkyl)phenyl, naphthyl, pyridinyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof; 1 -C 20 Alkyl group, C 3 -C 10 a cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group;

[0053] According to another embodiment, in Formula 2, R 14 Or R 16 are each independently deuterium, -F, a cyano group, or C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl groups, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 C substituted or unsubstituted with alkyl)phenyl, naphthyl, pyridinyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof; 1 -C 20 Alkyl group, C 3 -C 10It is a cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0054] According to yet another embodiment, in Formula 2, R 14 Or R 16 are each independently -CH 3 , -CH 2 CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CH 2 CD 3 , or -CD 2 CH 3 It is.

[0055] According to yet another embodiment, in Formula 2, R 14 Or R 16 are the same or different.

[0056] According to yet another embodiment, in Formula 2, R 11 is not hydrogen.

[0057] According to yet another embodiment, in Formula 2, R 11 is not hydrogen or a methyl group.

[0058] According to yet another embodiment, in Formula 2, R 11 is not a hydrogen atom, a methyl group, or a cyano group.

[0059] According to yet another embodiment, in Formula 2, R 11 is not hydrogen, but R 12 and R 13 is hydrogen.

[0060] According to yet another embodiment, in Formula 2, R 11 has 2 or more, 3 or more, or 4 or more carbons.

[0061] According to yet another embodiment, in Formula 2, R 11 teeth, Deuterium, -F, cyano group, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl groups, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 a methyl group substituted with an alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; or Deuterium, -F, cyano group, C 1 -C 20 Alkyl groups, deuterated C 1 -C 20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl groups, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20C substituted or unsubstituted with alkyl)phenyl, naphthyl, pyridinyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, or any combination thereof; 2 -C 20 Alkyl group, C 3 -C 10 a cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group;

[0062] According to still another embodiment, in Formula 3, Z 3 At least one C 1 -C 20 an alkyl group and at least one C 6 -C 20 C simultaneously substituted with aryl groups 6 -C 20 It is an aryl group.

[0063] According to still another embodiment, the above-mentioned Formula 3 satisfies at least one of the following <Condition A> and the following <Condition B>:

[0064] <Condition A> L 3 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, <Condition B> Z 3 is a substituted or unsubstituted C 6 -C 60 Aryl groups, 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.

[0065] According to still another embodiment, in Formulas 2 and 3, R 2 , R 11 Or R 16 , and Z 1 Or Z 3 , Z 19 , and Z 20 are each independently hydrogen, deuterium, -F, a cyano group, a nitro group, or -SF 5 , -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , -OCH 3 , -OCDH 2 , -OCD 2 H, -OCD 3 , -SCH 3 , -SCDH 2 , -SCD 2 H, -SCD 3 , a group represented by one of the following chemical formulae 9-1 to 9-39, a group in which at least one hydrogen of one of the following chemical formulae 9-1 to 9-39 is replaced with deuterium, a group in which at least one hydrogen of one of the following chemical formulae 9-1 to 9-39 is replaced with -F, a group represented by one of the following chemical formulae 9-201 to 9-230, a group in which at least one hydrogen of one of the following chemical formulae 9-201 to 9-230 is replaced with deuterium, a group in which at least one hydrogen of one of the following chemical formulae 9-201 to 9-230 is replaced with -F, a group represented by one of the following chemical formulas 10-1 to 10-145 in which at least one hydrogen of one of the following chemical formulas 10-1 to 10-145 is replaced with deuterium, a group represented by one of the following chemical formulas 10-1 to 10-145 in which at least one hydrogen of one of the following chemical formulas 10-1 to 10-145 is replaced with -F, a group represented by one of the following chemical formulas 10-201 to 10-354 in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-354 is replaced with deuterium, a group represented by one of the following chemical formulas 10-201 to 10-354 in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-354 is replaced with -F, 3 )(Q 4 )(Q 5 ), or -Ge(Q3 )(Q 4 )(Q 5 ) (However, the above Q 3 Or Q 5 For explanations of each, please refer to the respective parts described in this specification).

[0066] According to yet another embodiment, in Formula 2, R 11 represents a group represented by one of the following chemical formulae 9-1 to 9-39, a group in which at least one hydrogen atom in one of the following chemical formulae 9-1 to 9-39 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulae 9-1 to 9-39 is substituted with -F, a group represented by one of the following chemical formulae 9-201 to 9-230, a group in which at least one hydrogen atom in one of the following chemical formulae 9-201 to 9-230 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulae 9-201 to 9-230 is substituted with -F, a group represented by one of the following chemical formulas 10-1 to 10-145 in which at least one hydrogen atom is replaced by deuterium; a group represented by one of the following chemical formulas 10-1 to 10-145 in which at least one hydrogen atom is replaced by -F; a group represented by one of the following chemical formulas 10-201 to 10-354 in which at least one hydrogen atom is replaced by deuterium; or a group in which at least one hydrogen atom is replaced by -F.

[0067] According to still another embodiment, in Formula 3, Z 3 is a group represented by one of the following chemical formulas 10-12 to 10-145, a group in which at least one hydrogen of one of the following chemical formulas 10-12 to 10-145 is replaced with deuterium, a group in which at least one hydrogen of one of the following chemical formulas 10-12 to 10-145 is replaced with -F, a group represented by one of the following chemical formulas 10-201 to 10-354, a group in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-354 is replaced with deuterium, or a group in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-354 is replaced with -F.

[0068] [ka]

[0069] [ka]

[0070] [ka] [ka] [ka]

[0071] [ka] [ka] [ka] [ka]

[0072] In the above chemical formulas 9-1 to 9-39, 9-201 to 9-230, and the above chemical formulas 10-1 to 10-145, 10-201 to 10-354, * is a bonding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, TMG is a trimethylgermyl group, and OMe is a methoxy group.

[0073] The above "groups in which at least one hydrogen atom in the chemical formulae 9-1 to 9-39 has been replaced with deuterium" and "groups in which at least one hydrogen atom in the chemical formulae 9-201 to 9-230 has been replaced with deuterium" are, for example, groups represented by the following chemical formulae 9-501 to 9-514 and 9-601 to 9-637.

[0074] [ka]

[0075] [ka]

[0076] The above "groups in which at least one hydrogen atom in the chemical formulae 9-1 to 9-39 is substituted with -F" and "groups in which at least one hydrogen atom in the chemical formulae 9-201 to 9-230 is substituted with -F" are, for example, groups represented by the following chemical formulae 9-701 to 9-710.

[0077] [ka]

[0078] The above "groups in which at least one hydrogen atom in any of the chemical formulae 10-1 to 10-145 has been replaced with deuterium" and "groups in which at least one hydrogen atom in any of the chemical formulae 10-201 to 10-354 has been replaced with deuterium" are, for example, groups represented by the following chemical formulae 10-501 to 10-553.

[0079] [ka] [ka]

[0080] The above "groups in which at least one hydrogen atom in any of chemical formulae 10-1 to 10-145 has been substituted with -F" and "groups in which at least one hydrogen atom in any of chemical formulae 10-201 to 10-354 has been substituted with -F" are, for example, groups represented by the following chemical formulae 10-601 to 10-636.

[0081] [ka] [ka]

[0082] In the above formulas 2 and 3, a2, b1, and b2 are each R 2 , Z 1 , and Z 2 a2 is an integer of 0 to 20 (for example, an integer of 0 to 10), b1 is an integer of 0 to 5, and b2 is an integer of 0 to 4. When a2 is 2 or more, 2 or more R 2 are the same or different from each other, and when b1 is 2 or more, two or more Z 1 are the same or different from each other, and when b2 is 2 or more, two or more Z 2 are the same or different from each other.

[0083] For example, in the above formula 3, Z 1 is not hydrogen, and b1 is an integer of 1 to 5.

[0084] According to still another embodiment, in Formula 3, Z 2 is not hydrogen, and b2 is an integer of 1 to 4.

[0085] According to yet another embodiment, the organometallic compound represented by Formula 1 includes a deuterium group, a fluoro group, or a combination thereof.

[0086] According to still another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies at least one of the following <Condition 1> to <Condition 12>.

[0087] <Condition 1> R 11 contains at least one deuterium, not hydrogen, <Condition 2> At least one of R11 to R13 is not hydrogen and contains at least one deuterium. <Condition 3> a2 R 2At least one of the atoms is not hydrogen and contains at least one deuterium atom; <Condition 4> L 3 is not a single bond and contains at least one deuterium; <Condition 5> Z 3 contains at least one deuterium, not hydrogen, <Condition 6> b 1 Z 1 At least one of the atoms is not hydrogen and contains at least one deuterium atom; <Condition 7> R 11 is not hydrogen and contains at least one fluoro group; <Condition 8> Above R 11 Or R 13 at least one of which is not hydrogen and contains at least one fluoro group; <Condition 9> a2 R 2 at least one of which is not hydrogen and contains at least one fluoro group; <Condition 10> L 3 is not a single bond and contains at least one fluoro group; <Condition 11> Z 3 is not hydrogen and contains at least one fluoro group; <Condition 12> b 1 Z 1 At least one of is not hydrogen and contains at least one fluoro group.

[0088] In the above formulas 2 and 3, i) R 11 and R 12 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 ii) a plurality of R2 Two or more of the 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) a plurality of Z 1 Two or more of the 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 iv) a plurality of Z 2 Two or more of the 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 Forms a heterocyclic group. R 10a The description of Z 1 See the discussion of R 10a As used herein, Z 1 Refer to the explanation for, but not hydrogen.

[0089] In the above chemical formulas 2 and 3, * and *' are binding sites with adjacent atoms, respectively.

[0090] According to one embodiment, in Formula 2, [ka] is a group represented by the following chemical formula 2-1 or 2-2.

[0091] [ka]

[0092] In the above chemical formulas 2-1 and 2-2, X 11 and R 13 Or R 16 The explanations regarding are the same as those described in this specification, R 1 The explanation regarding R 12 Please refer to the explanation on a14 is an integer of 0 to 4, a18 is an integer from 0 to 8, *' is a bonding site with M in Chemical Formula 1; *” is a bonding site with adjacent atoms in chemical formula 2.

[0093] According to another embodiment, in Formula 2, [ka] The group represented by the following formulas CY2-1 to CY2-33 is a group represented by one of the following formulas CY2-1 to CY2-33.

[0094] [ka]

[0095] In the above chemical formulas CY2-1 to CY2-33, Y 21 and R 2 The explanations regarding are the same as those described in this specification, X 22 is C(R 22 )(R 23 ), N(R 22 ), O, S, or Si(R 22 )(R 23 ) and R 22 Or R 29 The explanations regarding R 2 Please refer to the explanation on a28 is an integer from 0 to 8, a26 is an integer from 0 to 6, a24 is an integer from 0 to 4, a23 is an integer from 0 to 3, a22 is an integer of 0 to 2, *" is a bonding site with adjacent atoms in chemical formula 2, * denotes a binding site with M in Chemical Formula 1.

[0096] According to yet another embodiment, in Formula 2, [ka] is a group represented by one of the following chemical formulas CY2(1) to CY2(56), or a group represented by one of the above chemical formulas CY2-11 to CY2-33.

[0097] [ka] [ka]

[0098] In the above chemical formulas CY2(1) to CY2(56), Y 21 is C, R 21 Or R 24 The explanations regarding R 2 Although the explanation of R 21 Or R 24 is not hydrogen, *" is a bonding site with adjacent atoms in chemical formula 2, * denotes a binding site with M in Chemical Formula 1.

[0099] According to yet another embodiment, in Formula 3, [ka] The group represented by the following formulas CY3-1 to CY3-6 is a group represented by the following formulas CY3-1 to CY3-6.

[0100] [ka]

[0101] In the above chemical formulas CY3-1 to CY3-6, X 1 , Z 1 The explanations regarding b1 and b2 are the same as those described in this specification, A 11 Or A 18 are each independently C or N, but A in the chemical formulas CY3-1 and CY3-6 13 Or A 18 At least one of the groups is N, and A of the chemical formulas CY3-2 and CY3-5 is 11 , A 14 , A 15 , A 16 , A 17 , and A 18 At least one of the groups is N, and A of the chemical formulas CY3-3 and CY3-4 is 11 , A 12 , A 15 , A 16 , A 17 , and A 18 At least one of is N; * is a binding site with M in Chemical Formula 1; *” is a bonding site with an adjacent atom in chemical formula 3.

[0102] According to yet another embodiment, in Formula 3, [ka] is a group represented by one of the following chemical formulas CY3-1-1 to CY3-1-6, CY3-2-1 to CY3-2-6, CY3-3-1 to CY3-3-6, CY3-4-1 to CY3-4-6, CY3-5-1 to CY3-5-6, and CY3-6-1 to CY3-6-6.

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] In the above chemical formulae CY3-1-1 to CY3-1-6, CY3-2-1 to CY3-2-6, CY3-3-1 to CY3-3-6, CY3-4-1 to CY3-4-6, CY3-5-1 to CY3-5-6, and CY3-6-1 to CY3-6-6, X 1 and Z 1 The explanations regarding are the same as those described in this specification, Z 1a The explanation regarding R 1a Please refer to the explanation on A 11 Or A 18 are each independently C or N, but a) A of the chemical formulae CY3-1-1, CY3-1-4, and CY3-6-1 and CY3-6-4 13 , A 14 , A 15 , and A 16at least one of the formulas CY3-1-2, CY3-1-5, and CY3-6-2 and CY3-6-5 is N; 13 , A 14 , A 15 , and A 18 at least one of the formulas CY3-1-3, CY3-1-6, and A of the formulas CY3-6-3 and CY3-6-6 is N; 13 , A 14 , A 17 , and A 18 at least one of the formulas CY3-2-1, CY3-2-4, and CY3-5-1 and CY3-5-4 is N; 11 , A 14 , A 15 , and A 16 at least one of the formulas CY3-2-2, CY3-2-5, and CY3-5-2 and CY3-5-5 is N; 11 , A 14 , A 15 , and A 18 f) at least one of the A of the formulae CY3-2-3, CY3-2-6, and CY3-5-3 and CY3-5-6 is N; 11 , A 14 , A 17 , and A 18 at least one of the formulas CY3-3-1, CY3-3-4, and A of the formulas CY3-4-1 and CY3-4-4 is N; 11 , A 12 , A 15 , and A 16 at least one of the formulas CY3-3-2, CY3-3-5, and A of the formulas CY3-4-2 and CY3-4-5 is N; 11 , A 12 , A 15 , and A 18 at least one of the formulas CY3-3-3, CY3-3-6, and CY3-4-3 and CY3-4-6 is N; 11 , A 12 , A 17 , and A 18At least one of is N; b13 is an integer of 0 to 3, b114 is an integer of 0 to 4, b118 is an integer from 0 to 8, * is a binding site with M in Chemical Formula 1; *” is a bonding site with an adjacent atom in chemical formula 3.

[0110] According to yet another embodiment, in Formula 3, [ka] The group represented by the following formula NCY3(1) to NCY3(84) is a group represented by one of the following chemical formulas.

[0111] [ka] [ka] [ka]

[0112] In the above chemical formulas NCY3(1) to NCY3(84), X 1 The explanation regarding is the same as that described in this specification, Z 11 Or Z 18 , and Z 11a Or Z 14a The explanation for each of these is given in the present specification as Z 1 Although the explanation is the same as for Z 11 Or Z 18 , and Z 11a Or Z 14a Each of the is not hydrogen, * is a binding site with M in Chemical Formula 1; *” is a bonding site with an adjacent atom in chemical formula 3.

[0113] According to yet another embodiment, in Formula 3, [ka] The group represented by the following formulas CY4-1 to CY4-60 is a group represented by one of the following formulas CY4-1 to CY4-60.

[0114] [ka] [ka]

[0115] In the above chemical formulas CY4-1 to CY4-60, L 3 and Z 3 The explanations regarding are the same as those described in this specification, Z 21 Or Z 24 The explanations regarding Z 2 Although the explanation is the same as for Z 21 Or Z 24 is not hydrogen, *' is a bonding site with M in Chemical Formula 1; *” is a bonding site with an adjacent atom in chemical formula 3.

[0116] According to yet another embodiment, in Formula 3, [ka] Multiple Z's in the group represented by 2 Two or more of the 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.

[0117] Therefore, in the above formula 3, [ka] The group represented by the following formula CY4(1) to CY4(4) is a group represented by one of the following chemical formulas CY4(1) to CY4(4).

[0118] [ka]

[0119] In the above chemical formulas CY4(1) to CY4(4), A 21 Or A 24 , L 3 , Z 2 , Z 3 , and R 10a The explanations regarding are the same as those described in this specification, b22 is an integer from 0 to 2, Ring CY 10 and CY 11 are independent of each other, C 5 -C 30 Carbocyclic group or C 1 -C 30 is a heterocyclic group, R 11a The explanation regarding R 10a Please refer to the explanation on b3 and b4 are each independently an integer of 0 to 20; when b3 is 2 or more, R 10a are the same or different from each other, and when b4 is 2 or more, 2 or more R 11a are the same or different from each other, *' is a bonding site with M in Chemical Formula 1; *” is a bonding site with an adjacent atom in chemical formula 3.

[0120] For example, in the above chemical formulas CY4(1) to CY4(4), the ring CY 10 and CY 11 are each independently a benzene group or a naphthalene group.

[0121] According to yet another embodiment, in Formula 3, [ka] is a group represented by one of the following chemical formulas CY4(1)-1 to CY4(1)-4, CY4(2)-1 to CY4(2)-4, CY4(3)-1 to CY4(3)-4, and CY4(4)-1.

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] [ka]

[0126] In the above chemical formulas CY4(1)-1 to CY4(1)-4, chemical formulas CY4(2)-1 to CY4(2)-4, chemical formulas CY4(3)-1 to CY4(3)-4, and chemical formula CY4(4)-1, A 21 Or A 24 , L 3 , Z 2 , Z 3 , and R 10a The explanations regarding are the same as those described in this specification, b22 is an integer from 0 to 2, R 11a The explanation regarding R 10a Refer to the explanation for b34 and b35. If b34 is 2 or more, R 10a are the same or different from each other, and when b44 is 2 or more, 2 or more R 10aare the same or different from each other, b34 and b44 are each independently an integer of 0 to 4; b36 is an integer of 0 to 6, and when b36 is 2 or more, R 10a are the same or different from each other, *' is a bonding site with M in Chemical Formula 1; *” is a bonding site with an adjacent atom in chemical formula 3.

[0127] According to an embodiment, the organometallic compound represented by Formula 1 emits red or green light, for example, red or green light having a maximum emission wavelength in the range of 500 nm or more, for example, 500 nm or more and 850 nm or less. For example, the organometallic compound emits green light.

[0128] For example, the organometallic compound is one of the following compounds 1-4010.

[0129] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0130] In the organometallic compound represented by the above chemical formula 1, L 1 and L 2 are ligands represented by the above formulas 2 and 3, respectively, and L 1 and L 2 The numbers n1 and n2 are each independently 1 or 2. That is, the organometallic compound has *-X as a substituent. 11 (R 14 )(R 15 )(R 16 ) group is always included in L 1 (Chemical Formula 2) and L 2 (Chemical Formula 3) is necessarily included. As a result, the molecular orientation and charge mobility of the organometallic compound represented by Chemical Formula 1 are greatly improved, and the external quantum efficiency and life span of an electronic device including the same, for example, an organic light emitting device, are improved.

[0131] 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.

[0132] [Table 1]

[0133] It can be seen from Table 1 above that the organometallic compound represented by Formula 1 above has electrical properties suitable for use as a dopant in electronic devices, for example, organic light emitting devices.

[0134] 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.

[0135] 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, an emission layer in the organic layer. According to another aspect, there is provided an organic light-emitting device having a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer contains at least one organometallic compound represented by Chemical Formula 1.

[0136] The organic light emitting device has an organic layer containing the organometallic compound represented by Chemical Formula 1, and thus has improved external quantum efficiency and improved life characteristics.

[0137] 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, for example, red or green light having a maximum emission wavelength in the range of 500 nm or more, for example, 500 nm or more and 850 nm or less. For example, the organometallic compound emits green light.

[0138] 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."

[0139] 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).

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is used.

[0145] The first electrode 11 is formed by providing a material for the first electrode on the upper part of the substrate by, for example, a deposition method or a sputtering method. The first electrode 11 is an anode. The material for the first electrode 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. The material for the first electrode includes 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.

[0146] 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.

[0147] On top of the first electrode 11, an organic layer 15 is disposed.

[0148] Organic layers 15 include a hole transport region, an emissive layer, and an electron transport region.

[0149] The hole transport region is disposed between the first electrode 11 and the light emitting layer.

[0150] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0151] 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.

[0152] 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.

[0153] 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 -3torr, and the deposition rate is selected from the range of about 0.01 to about 100 Å / sec.

[0154] 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.

[0155] The conditions for forming the hole transport layer and the electron blocking layer are the same as those for forming the hole injection layer.

[0156] 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.

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] 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 -C 10 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.

[0161] In the above formula 201, xa and xb are each independently an integer of 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is 0.

[0162] In the above chemical formulas 201 and 202, the above R 101Or R 108 , R 111 Or R 119 , and R 121 Or 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 10 Alkoxy 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.

[0163] 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 20Alkyl 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.

[0164] According to an embodiment, the compound represented by Formula 201 is represented by Formula 201A below.

[0165] [ka]

[0166] In the above formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed description, see above.

[0167] For example, the compound represented by the above chemical formula 201 and the compound represented by the above chemical formula 202 include the following compounds HT1 to HT20.

[0168] [ka] [ka]

[0169] 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 at least one layer of a hole injection layer and a hole transport layer, 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.

[0170] 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.

[0171] 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 tetracyanoquinone dimethane (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.

[0172] [ka]

[0173] The hole transport region further comprises a buffer layer.

[0174] The buffer layer compensates for the optical resonance distance according to the wavelength of light emitted from the light emitting layer, thereby increasing efficiency.

[0175] 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.

[0176] 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, but are generally selected from the same range of conditions as those for forming the hole injection layer.

[0177] The light-emitting layer includes a host and a dopant, and the dopant includes the organometallic compound represented by Chemical Formula 1 above.

[0178] The host includes TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof.

[0179] [ka]

[0180] 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.

[0181] 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.

[0182] 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 are exhibited without a substantial increase in driving voltage.

[0183] An electron transport region is then deposited on top of the light emitting layer.

[0184] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] [ka]

[0189] 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.

[0190] The electron transport layer includes BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof.

[0191] [ka]

[0192] Alternatively, the electron transport layer comprises one of the following compounds ET1 to ET25, or any combination thereof.

[0193] [ka] [ka]

[0194] 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.

[0195] The electron transport layer may further comprise a metal-containing material in addition to the materials described above.

[0196] The metal-containing material includes a Li complex. The Li complex includes, for example, the following compound ET-D1 (LiQ) or ET-D2.

[0197] [ka]

[0198] The electron transport region also includes an electron injection layer that facilitates the injection of electrons from the second electrode 19 .

[0199] The electron injection layer is LiF, NaCl, CsF, Li 2 O, BaO, or any combination thereof.

[0200] 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.

[0201] A second electrode 19 is provided 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 any combination thereof, 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.

[0202] Although the organic light-emitting device has been described above with reference to FIG. 1, the present invention is not limited thereto.

[0203] According to yet another aspect, the organic light emitting device is included in an electronic device. Thus, an electronic device including the organic light emitting device is provided. The electronic device may include, for example, a display, a lighting device, a sensor, and the like.

[0204] In yet another aspect, there is provided a diagnostic composition comprising one or more organometallic compounds represented by Formula 1 above.

[0205] The organometallic compound represented by Chemical Formula 1 provides high luminescence efficiency, and therefore a diagnostic composition containing the organometallic compound can have high diagnostic efficiency.

[0206] The diagnostic composition is used in a variety of applications, such as various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0207] In this specification, C 1 -C 60 An alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, C 1 -C 60 The alkylene group is C 1 -C 60 It means a divalent group having the same structure as an alkyl group.

[0208] 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 following groups may be included: 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.

[0209] In this specification, C 1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is C 1 -C 60 Specific examples of the aryl group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.

[0210] In this specification, C2 -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.

[0211] 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.

[0212] In this specification, C 3 -C 10 Cycloalkyl groups are C 3 -C 10 means a monovalent saturated hydrocarbon ring group, 3 -C 10 The cycloalkylene group is C 3 -C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0213] In this specification, C 3 -C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like.

[0214] In this specification, C 1 -C 10 The heterocycloalkyl group is a C aryl group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 1 -C 10 means a monovalent monocyclic group, C 1 -C 10 The heterocycloalkylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0215] In this specification, C 1 -C 10 Examples of heterocycloalkyl groups include silolanyl, silanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, and the like.

[0216] 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.

[0217] In this specification, C 1 -C 10 The heterocycloalkenyl group is a C alkyl group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 1 -C 10 It is a monovalent monocyclic group having at least one double bond in the ring. 1 -C 10Specific examples of 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.

[0218] In this specification, C 6 -C 60 Aryl groups are C 6 -C 60 means a monovalent radical having a carbocyclic aromatic system, C 6 -C 60 The arylene group is C 6 -C 60 C means a divalent group having a carbocyclic aromatic system. 6 -C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. 6 -C 60 Aryl groups and C 6 -C 60 When the arylene group contains more than one ring, the two or more rings are fused together.

[0219] In this specification, C 7 -C 60 The alkylaryl group has at least one C 1 -C 60 Alkyl-substituted C 6 -C 60 It means an aryl group.

[0220] In this specification, C 1 -C 60 The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and 1 -C 60 means a monovalent group having a cyclic aromatic system, C 1 -C 60The heteroarylene group contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B 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.

[0221] In this specification, C 2 -C 60 The alkylheteroaryl group has at least one C 1 -C 60 Alkyl-substituted C 1 -C 60 It means a heteroaryl group.

[0222] 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 104 is C 1 -C 60 (an alkyl group).

[0223] 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 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.

[0224] In the present specification, the monovalent non-aromatic hetero-condensed polycyclic group means a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed with each other and the ring-forming atoms include heteroatoms selected from N, O, P, Si, S, Se, Ge, and B in addition to carbon, and the entire molecule has non-aromaticity. The monovalent non-aromatic hetero-condensed polycyclic group includes a carbazolyl group. In the present specification, the divalent non-aromatic hetero-condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.

[0225] 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 group or a polycyclic group. 10a (or at least one Z 0 ) substituted or unsubstituted)C 5 -C 30 A "carbocyclic group" is, for example, 10a (or at least one Z 0) substituted or unsubstituted, ) adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, fluorene group, and the like.

[0226] In this specification, C 1 -C 30 The heterocyclic group refers to a saturated or unsaturated cyclic group having, as ring-forming atoms, 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B. The C1-C30 heterocyclic group is a monocyclic group or a polycyclic group. 10a (or at least one Z 0 ) substituted or unsubstituted)C 1 -C 30 The "heterocyclic group" is, for example, (at least one R 10a (or at least one Z 0) substituted or unsubstituted with a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzo Benzoselenophene group, dibenzogermole group, dibenzothiophene 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, azacarbaroyl group, azadibenzole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole 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, quinoxaline group, quinazoline group, Examples of such groups include a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole 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.

[0227] As another example, in the present specification, "C 5 -C 30 Carbocyclic group" and "C 1 -C 30Examples of the "heterocyclic group" include 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 cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an isoxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, a thiatriazole 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, a norbornene 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.

[0228] 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 The terms "heterocycloalkyl group" and "fluorinated phenyl group" refer to C-substituted phenyl groups each 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 An alkyl group (i.e., a fluoromethyl group) is -CF 3 , -CF 2 H, and -CFH 2 Contains fluoride C 1 -C60 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" or a "fluorinated phenyl group" refers to 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, fully fluorinated C 1 -C 10 or ii) a partially fluorinated C group in which all hydrogen atoms in each group are not 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 groups, partially fluorinated C 1 -C 10 It is a heterocycloalkyl group or a partially fluorinated phenyl group.

[0229] As used herein, "deuterated C 1 -C 60 Alkyl group (or deuterated C 1 -C 20 Alkyl groups, etc.), deuterated C 3 -C 10 Cycloalkyl group, deuterated C 1 -C 10 "Heterocycloalkyl group" and "deuterated phenyl group" refer to C phenyl groups each substituted with at least one deuterium. 1 -C 60 Alkyl group (or C 1 -C 20 Alkyl groups, etc.), C 3 -C 10Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups and phenyl groups. For example, "deuterated C 1 "Alkyl group (i.e., deuterated methyl group)" means -CD 3 , -CD 2 H, and -CDH 2 Deuterated C 3 -C 10 For examples of "cycloalkyl groups", see, for example, Chemical Formula 10-501 above. 1 -C 60 Alkyl group (or deuterated C 1 -C 20 Alkyl groups, etc.), deuterated C 3 -C 10 Cycloalkyl group, deuterated C 1 -C 10 A "heterocycloalkyl group" or a "deuterated phenyl group" refers to a fully deuterated C 1 -C 60 Alkyl group (or fully deuterated C 1 -C 20 Alkyl groups, etc.), fully deuterated C 3 -C 10 Cycloalkyl groups, fully deuterated C 1 -C 10 a heterocycloalkyl group, or a fully deuterated phenyl group, or ii) a partially deuterated C 1 -C 60 Alkyl group (or partially deuterated C 1 -C 20 Alkyl groups, etc.), partially deuterated C 3 -C 10 Cycloalkyl groups, partially deuterated C 1 -C 10 It is a heterocycloalkyl group or a partially deuterated phenyl group.

[0230] In this specification, "(C 1 -C 20 (alkyl) "X group" means at least one C 1 -C20 The term "X group" refers to a 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.

[0231] 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.

[0232] The above substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -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 60 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 substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are Deuterium, -F, -Cl, -Br, -I, -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 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C1 -C 60 Alkoxy group or C 1 -C 60 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 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, C1 -C 60 Alkoxy group or C 1 -C 60 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 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 1 -C 60 Alkylthio 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 )(Q29 ), 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 -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 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;

[0233] In this specification, Q 1 Or Q 9 , Q 11 Or Q 19 , Q 21 Or Q 29 , and Q 31 Or 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; deuterium, -F, C 1 -C60 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 1 -C 60 Alkylthio 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, -F, 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.

[0234] For example, in this specification, Q 1 Or Q 9 , Q 11 Or Q 19 , Q 21 Or Q 29 , and Q 31 Or Q 39 are each independently -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CH 2 CH3 , -CH 2 CD 3 , -CH 2 CD 2 H, -CH 2 CDH 2 , -CHDCH 3 , -CHDCD 2 H, -CHDCDH 2 , -CHDCD 3 , -CD 2 CD 3 , -CD 2 CD 2 H or -CD 2 CDH 2 or Deuterium, 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;

[0235] 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.

[0236] [Example]

[0237] ≪Synthesis example 1 (compound 15)≫

[0238] [ka]

[0239] <Synthesis of compound 15A>

[0240] 4-Isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (7.5g, 26.7mmol) and iridium chloride (4.1g, 11.9mmol) were mixed with 120mL of ethoxyethanol and 40mL of distilled water, and then refluxed and stirred for 24 hours, and then cooled to room temperature. The solid product was separated by filtration, thoroughly washed with water / methanol / hexane in that order, and the solid product was dried in a vacuum oven to obtain 7.43g of compound 15A (79% yield).

[0241] <Synthesis of compound 15B>

[0242] Compound 15A (3.0 g, 1.91 mmol) was mixed with 60 mL of methylene chloride, and then AgOTf (0.98 g, 3.81 mmol) was mixed with 20 mL of methanol and added. After stirring at room temperature for 18 hours while blocking light with aluminum foil, the solid formed was removed by filtration through Celite, and the filtrate was reduced in pressure to obtain a solid (compound 15B), which was used in the next reaction without further purification.

[0243] <Synthesis of compound 15>

[0244] Compound 15B (3.68 g, 3.79 mmol) and 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine (2.24 g, 4.17 mmol) were mixed with 50 mL of 2-ethoxyethanol and 50 mL of dimethylformamide, and the mixture was refluxed and stirred at 130°C for 48 hours, and then the temperature was lowered. The mixture obtained therefrom was reduced in pressure to obtain a solid, and chromatographic chromatography was performed under MC (methylene chloride):hexane conditions to obtain 2.0 g of compound 15 (41% yield). The substance was confirmed through mass and HPLC analysis. HRMS(MALDI) calcd for C 73 H 80 IrN 5 OSi 2 :m / z 1291.5531 found:1291.5529

[0245] ≪Synthesis Example 2 (Compound 295)≫

[0246] [ka]

[0247] Instead of 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine, 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-5-methyl-2-phenylbenzofuro[2,3-b]pyridine was used, but the same synthesis method as that of compound 15 in Synthesis Example 1 was used to obtain compound 295 (0.78 g, 39% yield). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 81 H 88 IrN 5 OSi 2 :m / z 1395.9863 found:1395.96

[0248] ≪Synthesis Example 3 (Compound 184)≫

[0249] [ka]

[0250] <Synthesis of compound 184A>

[0251] Compound 184A (7.1 g, 71% yield) was obtained using the same method as that for compound 15A in Synthesis Example 1 above, except that 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0252] <Synthesis of compound 184B>

[0253] Compound 184B was obtained by the same method as that for synthesizing compound 15B in Synthesis Example 1 above, except that compound 184A was used instead of compound 15A. The obtained compound 184B was used in the next reaction without further purification.

[0254] <Synthesis of compound 184>

[0255] Compound 15B was replaced with compound 184B, and 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was replaced with 8-(1-(3,5-isopropyl-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine. The same synthesis method as that of compound 15 in Synthesis Example 1 was used to obtain 0.53 g (28% yield) of compound 184. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 60 H 70 IrN 5 OSi 2 :m / z 1125.4748 found:1125.4744

[0256] ≪Synthesis Example 4 (Compound 212)≫

[0257] [ka]

[0258] <Synthesis of compound 212A>

[0259] 2-Phenyl-5-(trimethylsilyl)pyridine (7.5g, 33.1mmol) and iridium chloride (5.2g, 14.7mmol) were mixed with 120mL of ethoxyethanol and 40mL of distilled water, and then refluxed and stirred for 24 hours, and then cooled to room temperature. The solid product was separated by filtration, thoroughly washed with water / methanol / hexane in that order, and the solid product was dried in a vacuum oven to obtain 8.2g of compound 212A (82% yield).

[0260] <Synthesis of compound 212B>

[0261] Compound 212A (1.6 g, 1.2 mmol) was mixed with 45 mL of methylene chloride, and then AgOTf (0.6 g, 2.3 mmol) was mixed with 15 mL of methanol and 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 212B), which was used in the next reaction without further purification.

[0262] <Synthesis of compound 212>

[0263] Compound 212B (1.49 g, 1.74 mmol) and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine (0.97 g, 1.91 mmol) were mixed with 20 mL of 2-ethoxyethanol and 20 mL of dimethylformamide, and the mixture was refluxed and stirred at 130 ° C for 48 hours, after which the temperature was lowered. The mixture obtained therefrom was reduced in pressure to obtain a solid, which was subjected to column chromatography under MC:hexane conditions to obtain 0.73 g of compound 212 (37% yield). The substance was confirmed through mass and HPLC analysis. HRMS(MALDI) calcd for C 63 H 60 IrN 5 OSi 2 :m / z 1151.3699 found:1151.3698

[0264] ≪Synthesis Example 5 (Compound 487)≫

[0265] [ka]

[0266] <Synthesis of compound 487A>

[0267] Compound 487A (3.4 g, 74% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4 above, except that 2,4-diphenyl-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine.

[0268] <Synthesis of compound 487B>

[0269] Compound 487B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 487A was used instead of compound 212A. The obtained compound 487B was used in the next reaction without further purification.

[0270] <Synthesis of Compound 487>

[0271] Compound 487B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-([1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine, except that the same method as the synthesis method of compound 212 in Synthesis Example 4 was used to obtain 0.84g of compound 487 (42% yield). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 71 H 60 IrN 5 OSi 2:m / z 1247.6570 found:1247.6571

[0272] ≪Synthesis Example 6 (Compound 982)≫

[0273] [ka]

[0274] <Synthesis of compound 982A>

[0275] Instead of 2-phenyl-5-(trimethylsilyl)pyridine, 2-(p-tolyl-D 3 Compound 982A (5.3 g, 79% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4 above, except that 2-(trimethylsilyl)pyridine was used.

[0276] <Synthesis of compound 982B>

[0277] Compound 982B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 982A was used instead of compound 212A. The obtained compound 982B was used in the next reaction without further purification.

[0278] <Synthesis of Compound 982>

[0279] Compound 982B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine. The same synthesis method as that of compound 212 in Synthesis Example 4 was used to obtain 0.78 g (39% yield) of compound 982. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 71 H 62 D 6 IrN 5 OSi 2 :m / z 1261.4968 found:1261.4956

[0280] ≪Synthesis Example 7 (Compound 1042)≫

[0281] [ka]

[0282] <Synthesis of compound 1042A>

[0283] Instead of 2-phenyl-5-(trimethylsilyl)pyridine, 4-isobutyl (D 2 Compound 1042A (2.5 g, 68% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4 above, except that 1-2-phenyl-5-(trimethylsilyl)pyridine was used.

[0284] <Synthesis of compound 1042B>

[0285] Compound 1042B was obtained by the same method as that for compound 212B in Synthesis Example 4 above, except that compound 1042A was used instead of compound 212A. The obtained compound 1042B was used in the next reaction without further purification.

[0286] <Synthesis of compound 1042>

[0287] Compound 1042B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(2,6-diisopropylphenyl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine. The same synthesis method as that of compound 212 in Synthesis Example 4 was used to obtain 0.49g (33% yield) of compound 1042. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 67 H 71 D 4 IrN 4 OSi 2 :m / z 1204.5360 found:1204.5364.

[0288] ≪Synthesis Example 8 (Compound 1229)≫

[0289] [ka]

[0290] Compound 212B was replaced with compound 982B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was replaced with 8-(3-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-3H-imidazol[4,5-c]pyridin-2-yl)-2,5-dimethyl(D6)benzofuro[2,3-b]pyridine. The same synthesis method as that of compound 212 in Synthesis Example 4 was used to obtain 0.35g (23% yield) of compound 1229. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 68 H 58 D 12 IrN 6 OSi2 :m / z 1234.5454 found:1234.5450.

[0291] ≪Synthesis Example 9 (Compound 1550)≫

[0292] [ka]

[0293] <Synthesis of compound 1550A>

[0294] The same synthesis method as in Synthesis Example 1 for compound 15A was used, except that 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylgermyl)pyridine, to obtain 3.3 g (65% yield) of compound 1550A.

[0295] <Synthesis of compound 1550B>

[0296] Compound 1550B was obtained by the same method as that for synthesizing compound 15B in Synthesis Example 1 above, except that compound 1550A was used instead of compound 15A. The obtained compound 1550B was used in the next reaction without further purification.

[0297] <Synthesis of compound 1550>

[0298] Compound 15B was replaced with compound 1550B, and 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was replaced with 8-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2,5-methyl(D6)benzofuro[2,3-b]pyridine. The same synthesis method as that of compound 15 in Synthesis Example 1 was used to obtain 0.56g (28% yield) of compound 1550. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 74 H 76 D 6 Ge 2 IrN 5 O:m / z 1403.4949 found:1403.4946

[0299] ≪Synthesis Example 10 (Compound 1725)≫

[0300] [ka]

[0301] <Synthesis of compound 1725A>

[0302] Compound 1725A (2.1 g, 61% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4 above, except that 2-phenyl-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-5-(trimethylgermyl)pyridine.

[0303] <Synthesis of compound 1725B>

[0304] Compound 1725B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 1725A was used instead of compound 212A. The obtained compound 1725B was used in the next reaction without further purification.

[0305] <Synthesis of compound 1725>

[0306] Compound 1725B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-phenylbenzofuro[2,3-b]pyridine, except that the same method as the synthesis method of compound 212 in Synthesis Example 4 was used to obtain compound 1725 0.76g (38% yield). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 70 H 66 Ge 2 IrN 5 O:m / z 1333.3320 found:1333.3318

[0307] ≪Synthesis Example 11 (Compound 2610)≫

[0308] [ka]

[0309] <Synthesis of compound 2610A>

[0310] Compound 2610A (2.4 g, 64% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4 above, except that 2-(p-tolyl-D5)-5-(trimethylsilyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine.

[0311] <Synthesis of compound 2610B>

[0312] Compound 2610B was obtained using the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 2610A was used instead of compound 212A. The obtained compound 2610B was used in the next reaction without further purification.

[0313] <Synthesis of compound 2610>

[0314] Compound 2610B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzo[4,5]thieno[2,3-b]pyridine. The same synthesis method as that of compound 212 in Synthesis Example 4 was used to obtain 0.73 g (37% yield) of compound 2610. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 67 H 58 D 10 IrN 5 SSi 2 :m / z 1233.4991 found:1233.4988

[0315] ≪Synthesis Example 12 (Compound 2755)≫

[0316] [ka]

[0317] <Synthesis of compound 2755A>

[0318] Instead of 2-phenyl-5-(trimethylsilyl)pyridine, 4-neopentyl (D 2 Compound 2755A (4.2 g, 81% yield) was obtained using the same method as that for synthesis of compound 212A in Synthesis Example 4, except that 2-phenyl-5-(trimethylsilyl)pyridine was used.

[0319] <Synthesis of compound 2755B>

[0320] Compound 2755B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 2755A was used instead of compound 212A. The obtained compound 2755B was used in the next reaction without further purification.

[0321] <Synthesis of compound 2755>

[0322] Compound 212B was replaced by compound 2755B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was replaced by 6-(1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine, but the same synthesis method as that of compound 212 in Synthesis Example 4 was used to obtain 0.65 g (33% yield). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 75 H 80 IrN 5 OSi 2 :m / z 1323.6095 found:1323.6090

[0323] ≪Synthesis Example 13 (Compound 3214)≫

[0324] [ka]

[0325] <Synthesis of compound 3214A>

[0326] Compound 3214A (8.0 g, 80% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4 above, except that 2-phenyl-5-(trimethylsilyl)pyridine was replaced with 2-phenyl-4-(propan-2-yl-2-D)-5-(trimethylgermyl)pyridine.

[0327] <Synthesis of compound 3214B>

[0328] Compound 3214B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 3214A was used instead of compound 212A. The obtained compound 3214B was used in the next reaction without further purification.

[0329] <Synthesis of compound 3214>

[0330] Compound 3214B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(2,4-dimethyldibenzo[b,d]furan-3-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine, except that the same method as the synthesis method of compound 212 in Synthesis Example 4 was used to obtain 0.76 g (38% yield) of compound 3214. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 67 H 64 D 2 Ge 2 N 5 O 2 :m / z 1315.3395 found:1315.3394

[0331] ≪Synthesis Example 14 (Compound 3275)≫

[0332] [ka]

[0333] <Synthesis of compound 3275A>

[0334] The same synthesis method as in Synthesis Example 4 of compound 212A was used, except that 2-(4-(methyl-d3)phenyl)-4-(propan-2-yl 2-D)-5-(trimethylgermyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine, to obtain 8.5 g (71% yield) of compound 3275A.

[0335] <Synthesis of compound 3275B>

[0336] Compound 3275B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 3275 was used instead of compound 212A. The obtained compound 3275B was used in the next reaction without further purification.

[0337] <Synthesis of compound 3275>

[0338] Compound 3275B was used instead of compound 212B, and 4-(1-(2,6-diisopropylphenyl)-1H-benzo[d]imidazol-2-yl)-9-propylbenzofuro[2,3-b]quinoline was used instead of 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine, except that the same method as the synthesis method of compound 212 in Synthesis Example 4 was used to obtain compound 3275 (0.61 g, 34% yield). The substance was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 70 H 67 D 8 FGe 2 IrN 5 O:m / z 1369.4511 found:1369.4509

[0339] ≪Synthesis Example 15 (Compound 3492)≫

[0340] [ka]

[0341] <Synthesis of compound 3492A>

[0342] Instead of 2-phenyl-5-(trimethylsilyl)pyridine, 2-(2-fluoro-4-(methyl-d 3 Compound 3492A (9.0 g, 75% yield) was obtained using the same method as that for compound 212A in Synthesis Example 4, except that 5-(trimethylgermyl)pyridine was used.

[0343] <Synthesis of compound 3492B>

[0344] Compound 3492B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 3492A was used instead of compound 212A. The obtained compound 3492B was used in the next reaction without further purification.

[0345] <Synthesis of compound 3492>

[0346] Compound 3492B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(4-(tert-butyl)-2,6-diisopropylphenyl)-1H-benzo[d]imidazol-2-yl)-2-(4-(methyl-d 3 The same synthesis method as in Synthesis Example 4 of Compound 212 was used, except that 2,3-b-phenyl-benzofuro[2,3-b]-pyridine was used, to obtain 20.59 g (35% yield) of Compound 349. The material was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 71 H 65 D 9 F 2 Ge 2 IrN 5O:m / z 1400.4479 found:1400.4477

[0347] ≪Synthesis Example 16 (Compound 3553)≫

[0348] [ka]

[0349] <Synthesis of compound 3553A>

[0350] The same synthesis method as in Synthesis Example 4 for compound 212A was used, except that 4-(2,2-dimethylpropyl-1,1-d2)-2-phenyl-5-(trimethylgermyl)pyridine was used instead of 2-phenyl-5-(trimethylsilyl)pyridine, to obtain 8.5 g (77% yield) of compound 3553A.

[0351] <Synthesis of compound 3553B>

[0352] Compound 3553B was obtained by the same method as that for synthesizing compound 212B in Synthesis Example 4 above, except that compound 3553A was used instead of compound 212A. The obtained compound 3553B was used in the next reaction without further purification.

[0353] <Synthesis of compound 3553>

[0354] Compound 3553B was used instead of compound 212B, and 8-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-2-methylbenzofuro[2,3-b]pyridine was used instead of 8-(1-(2,6-diisopropylphenyl)-1H-naphtho[1,2-d]imidazol-2-yl)-2-(phenylmethyl-d 2) Compound 35530.55g (32% yield) was obtained using the same method as in the synthesis of compound 212 in Synthesis Example 4, except that benzofuro[2,3-b]pyridine was used. The material was identified through mass and HPLC analysis. HRMS(MALDI) calcd for C 79 H 80 D 6 Ge 2 IrN 5 O:m / z 1467.5262 found:1467.5260

[0355] Example 1

[0356] To prepare an anode, a glass substrate with an ITO pattern was cut to a size of 50 mm x 50 mm x 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.

[0357] On top of the anode, the compounds HT3 and F6-TCNNQ were vacuum co-deposited in a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and on top of the hole injection layer, the compound HT3 was vacuum deposited to form a hole transport layer having a thickness of 1,650 Å.

[0358] Subsequently, the compound CBP (host) and the compound 15 (dopant) were co-deposited on the hole transport layer at a weight ratio of 95:5 to form a 400 Å-thick light-emitting layer.

[0359] Then, compounds ET3 and ET-D1 were co-evaporated in a volume ratio of 50:50 on top of the light-emitting layer to form a 350 Å-thick electron transport layer, ET-D1 was vacuum-evaporated on top of the electron transport layer to form a 10 Å-thick electron injection layer, and Al was vacuum-evaporated on top of the electron injection layer to form a 1,000 Å-thick cathode, thereby producing an organic light-emitting element.

[0360] [ka]

[0361] <<Examples 2 to 15 and Comparative Examples A to C>>

[0362] An organic light emitting device was prepared in the same manner as in Example 1, except that, in forming the light emitting layer, the compounds shown in Table 2 below were used as the dopant instead of Compound 15.

[0363] <Evaluation Example 1>

[0364] The maximum external quantum efficiency (Max EQE), roll-off ratio, and lifetime (LT) of each of the organic light-emitting devices manufactured in Examples 1 to 15 and Comparative Examples A to C were measured. 97 The results are shown in Table 2 below. A current / voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment, and the life span (LT 97 ) (at 9,000 nit) was evaluated as the time (hr) it took to reach 97% brightness from the initial brightness of 100%, and expressed as a relative value (%). The roll-off ratio was calculated using the following formula 20.

[0365] [Number 1] Roll-off ratio={1-(Efficiency (at 9,000nit) / Maximum luminous efficiency)}×100%

[0366] [Table 2]

[0367] [ka]

[0368] From Table 2 above, it can be seen that the organic light-emitting devices of Examples 1 to 15 have improved external quantum efficiency, improved roll-off ratio, and improved lifetime characteristics compared to the organic light-emitting devices of Comparative Examples A to C.

[0369] 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]

[0370] 10 Organic light-emitting device 11 1st electrode 15 Organic layer 19 Second electrode

Claims

1. 1. An organometallic compound represented by the following chemical formula 1: [Chemical 1] M(L １ ) ｎ１ (L ２ ) ｎ２ ・・・(Chemical formula 1) In the above Chemical Formula 1, M is Ir; L １ is a ligand represented by the following chemical formula 2: L ２ is a ligand represented by the following chemical formula 3: n1 and n2 are each independently 1 or 2, the sum of n1 and n2 is 3, and when n1 is 2, two L １ are the same or different from each other, and when n2 is 2, two L ２ are the same or different from each other, 【Chemistry 2】 【Chemistry 3】 In the above Chemical Formulas 2 and 3, Y ２１ is C, Ring CY ２ is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a benzene group condensed with a norbornane group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group, X １１ is Si or Ge, X １ is O or S, A １１ Or A １４ are each independently C or N, but A １１ Or A １４ One of the formulas is represented by the formula 3. 【Chemistry 3-(1)】 and C bonded to a group represented by the formula: １１ Or A １４ one of which is C bound to M in Formula 1; A １５ Or A １８ , and A ２１ Or A ２４ are each independently C or N; A １１ Or A １８ At least one of is N; L ３ 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, R １４ Or R １６ are each independently deuterium, -F, a cyano group, C １ -C ２０ Alkyl groups, deuterated C １ -C ２０ Alkyl groups, fluorinated C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups, fluorinated C ３ -C １０ Cycloalkyl groups, (C １ -C ２０ Alkyl)C ３ -C １０ Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C １ -C ２０ C substituted or unsubstituted with alkyl)phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, or any combination thereof; １ -C ２０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; R ２ , R １１ Or R １３ , and Z １ Z 3 to Z 4 are each independently hydrogen, deuterium, —F, a cyano group, or a substituted or unsubstituted C １ -C ６０ Alkyl group, substituted or unsubstituted C ２ -C ６０ Alkenyl group, substituted or unsubstituted C １ -C ６０ Alkoxy group, substituted or unsubstituted C １ -C ６０ Alkylthio group, substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C ６ -C ６０ Aryl group, substituted or unsubstituted C ６ -C ６０ Aryloxy group, substituted or unsubstituted C ６ -C ６０ Arylthio group, substituted or unsubstituted C １ -C ６０ a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ３ ) (Q ４ ) (Q ５ ), or -Ge(Q ３ ) (Q ４ ) (Q ５ ) and a2 is an integer from 0 to 10, and when a2 is 2 or more, 2 or more R ２ are the same or different from each other, b1 is an integer of 0 to 5. When b1 is 2 or more, 2 or more Z １ are the same or different from each other, b2 is an integer of 0 to 4, and when b2 is 2 or more, 2 or more Z ２ are the same or different from each other, R １１ and R １２ 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 Two or more of the 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, Multiple Zs １ Two or more of the 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 Zs ２ Two or more of the 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 The explanation regarding Z 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 １ -C ６０ Alkoxy groups, substituted C １ -C ６０ Alkylthio group, substituted C ３ -C １０ Cycloalkyl groups, substituted C ６ -C ６０ Aryl groups, substituted C ６ -C ６０ Aryloxy groups, substituted C ６ -C ６０ Arylthio group, substituted C １ -C ６０ The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are Deuterium, -F, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , cyano group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C １ -C ６０ Alkoxy group, or C １ -C ６０ An alkylthio group; Deuterium, -F, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , cyano group, C ３ -C １０ Cycloalkyl group, C ６ -C ６０ aryl groups, or any combination thereof; １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C １ -C ６０ Alkoxy group, or C １ -C ６０ An alkylthio group; Deuterium, -F, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , cyano group, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C １ -C ６０ Alkoxy group, C １ -C ６０ Alkylthio group, C ３ -C １０ Cycloalkyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ C, substituted or unsubstituted with a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof; ３ -C １０ Cycloalkyl 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; -Si(Q ３３ ) (Q ３４ ) (Q ３５ ), or -Ge(Q ３３ ) (Q ３４ ) (Q ３５ ), or any combination thereof; Q ３ Or Q ５ , and Q ３３ Or Q ３５ are each independently Hydrogen; Deuterium; -F; Cyano group; a C1-C60 alkyl group unsubstituted or substituted with deuterium, -F, or any combination thereof; or Deuterium, -F, C １ -C ６０ Alkyl group, or C ６ -C ６０ an aryl group;

2. Said L ３ teeth, A single bond; or Deuterium, -F, cyano group, C １ -C ２０ Alkyl groups, deuterated C １ -C ２０ Alkyl groups, fluorinated C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups, fluorinated C ３ -C １０ Cycloalkyl groups, (C １ -C ２０ Alkyl)C ３ -C １０ Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C １ -C ２０ 2. The organometallic compound of claim 1, wherein the aryl group is a benzene, naphthalene, dibenzofuran, or dibenzothiophene group, substituted or unsubstituted with an alkyl (alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.

3. The R ２ , R １１ Or R １３ , and Z １ to Z 3 are each independently Hydrogen, deuterium, -F, or a cyano group; or Deuterium, -F, cyano group, C １ -C ２０ Alkyl groups, deuterated C １ -C ２０ Alkyl groups, fluorinated C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups, fluorinated C ３ -C １０ Cycloalkyl groups, (C １ -C ２０ Alkyl)C ３ -C １０ Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C １ -C ２０ C substituted or unsubstituted with alkyl)phenyl groups, naphthyl groups, pyridinyl groups, furanyl groups, thiophenyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzofuranyl groups, dibenzothiophenyl groups, or any combination thereof; １ -C ２０ Alkyl group, C ３ -C １０ 2. The organometallic compound according to claim 1, which is a cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

4. The R １１ 2. The organometallic compound of claim 1, wherein is not hydrogen.

5. 2. The organometallic compound according to claim 1, which satisfies at least one of the following <Condition A> and the following <Condition B>: <Condition A> L ３ 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, <Condition B> Z ３ is a substituted or unsubstituted C ６ -C ６０ Aryl 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.

6. Said Z １ 2. The organometallic compound according to claim 1, wherein b1 is not hydrogen and b2 is an integer from 1 to 5.

7. In the above Chemical Formula 2, 【Chemical 2-CY2】 The organometallic compound according to claim 1, wherein the group represented by the formula: is a group represented by one of the following chemical formulas CY2-1 and CY2-11 to CY2-25. 【Chemistry (CY2-1)(CY2-11)-(CY2-25)】 In the chemical formulae CY2-1 and CY2-11 to CY2-25, Y ２ and R ２ The explanations regarding are the same as those described in claim 1, X ２２ is C(R ２２ ) (R ２３ ), N(R ２２ ), O, S, or Si(R ２２ ) (R ２３ ) and R ２２ Or R ２９ The explanation for each is in claim 1, ２ Please refer to the explanation on a26 is an integer from 0 to 6, a24 is an integer from 0 to 4, a22 is an integer from 0 to 2, *" is a bonding site with an adjacent atom in chemical formula 2, * denotes the binding site with M in Chemical Formula 1.

8. In the above Chemical Formula 3, 【Chemistry 3-(2)】 The organometallic compound according to claim 1, wherein the group represented by the formula: is a group represented by one of the following chemical formulas CY3-1 to CY3-6. 【Chemistry (CY3-1)-(CY3-6)】 In the chemical formulas CY3-1 to CY3-6, X １ , Z １ The explanations regarding b1 and b2 are the same as those described in claim 1, A １１ Or A １８ are each independently C or N, but A in the formulae CY3-1 and CY3-6 １３ Or A １８ At least one of A in the formula CY3-2 and CY3-5 is N. １１ , A １４ , A １５ , A １６ , A １７ , and A １８ At least one of A in the formula CY3-3 and CY3-4 is N. １１ , A １２ , A １５ , A １６ , A １７ , and A １８ At least one of is N; * is a bonding site with M in Chemical Formula 1; *" is a bonding site with an adjacent atom in chemical formula 3.

9. In the above Chemical Formula 3, 【Chemistry 3-(2)】 The organic metal compound according to claim 1, characterized in that the group represented by the formula (I) is one of the following formulas: CY3-1-1 to CY3-1-6, CY3-2-1 to CY3-2-6, CY3-3-1 to CY3-3-6, CY3-4-1 to CY3-4-6, CY3-5-1 to CY3-5-6, and CY3-6-1 to CY3-6-6. 【Chemistry (CY3-1-1)-(CY3-1-6)】 【Chemistry (CY3-2-1)-(CY3-2-6)】 【Chemistry (CY3-3-1)-(CY3-3-6)】 【Chemistry (CY3-4-1)-(CY3-4-6)】 【Chemistry (CY3-5-1)-(CY3-5-6)】 【Chemistry (CY3-6-1)-(CY3-6-6)】 In the formulae CY3-1-1 to CY3-1-6, CY3-2-1 to CY3-2-6, CY3-3-1 to CY3-3-6, CY3-4-1 to CY3-4-6, CY3-5-1 to CY3-5-6, and CY3-6-1 to CY3-6-6, X １ and Z １ The explanations regarding are the same as those described in claim 1, Z １ａ For the description of R 10a in claim 1, A １１ Or A １８ are each independently C or N, but a) A in the formulae CY3-1-1, CY3-1-4, and CY3-6-1 and CY3-6-4 １３ , A １４ , A １５ , and A １６ is N; and b) A of formulas CY3-1-2, CY3-1-5, and formulas CY3-6-2 and CY3-6-5 is N. １３ , A １４ , A １５ , and A １８ is N; c) A of the formulae CY3-1-3 and CY3-1-6, and A of the formulae CY3-6-3 and CY3-6-6 are １３ , A １４ , A １７ , and A １８ is N; d) A of the formulae CY3-2-1, CY3-2-4, and CY3-5-1 and CY3-5-4 is １１ , A １４ , A １５ , and A １６ is N; e) A of the formulae CY3-2-2, CY3-2-5, and CY3-5-2 and CY3-5-5 is １１ , A １４ , A １５ , and A １８ f) at least one of the A of the formulae CY3-2-3, CY3-2-6, and CY3-5-3 and CY3-5-6 is N; １１ , A １４ , A １７ , and A １８ at least one of the formulas CY3-3-1, CY3-3-4, and A of the formulas CY3-4-1 and CY3-4-4 is N; １１ , A １２ , A １５ , and A １６ at least one of the formulas CY3-3-2, CY3-3-5, and CY3-4-2 and CY3-4-5 is N; １１ , A １２ , A １５ , and A １８ at least one of the formulas CY3-3-3, CY3-3-6, and CY3-4-3 and CY3-4-6 is N; １１ , A １２ , A １７ , and A １８ At least one of is N; b13 is an integer from 0 to 3, b114 is an integer from 0 to 4, b118 is an integer from 0 to 8, * is a bonding site with M in Chemical Formula 1; *" is a bonding site with an adjacent atom in chemical formula 3.

10. In the above Chemical Formula 3, 【Chemistry 3-(2)】 The organometallic compound according to claim 1, wherein the group represented by the formula: is a group represented by one of the following chemical formulas: NCY3(1) to NCY3(84). 【NCY3(1)-NCY3(29)】 【NCY3(30)-NCY3(57)】 【NCY3(58)-NCY3(84)】 In the above chemical formulas NCY3(1) to NCY3(84), X １ The explanation regarding is the same as that described in claim 1, Z １１ and Z 13 to Z 17, and Z １１ａ Or Z １４ａ The explanation for each of the above is given in claim 1. １ Although the explanation is the same as for Z １１ and Z 13 to Z 17, and Z １１ａ Or Z １４ａ Each of the is not hydrogen, * is a bonding site with M in Chemical Formula 1; *" is a bonding site with an adjacent atom in chemical formula 3.

11. In the above Chemical Formula 3, 【Chemistry 3-(1)】 The organometallic compound according to claim 1, wherein the group represented by the formula: is a group represented by one of the following chemical formulas CY4-1 to CY4-60. [Chemical formula (CY4-1)-(CY4-30)] [Chemical formula (CY4-31)-(CY4-60)] In the chemical formulas CY4-1 to CY4-60, L ３ and Z ３ The explanations regarding are the same as those described in claim 1, Z ２１ Or Z ２４ The explanation for each of the above is given in claim 1. ２ Although the explanation is the same as for Z ２１ Or Z ２４ is not hydrogen, *' is a bonding site with M in Chemical Formula 1; *" is a bonding site with an adjacent atom in chemical formula 3.

12. In the above Chemical Formula 3, 【Chemistry 3-(1)】 The organometallic compound according to claim 1, characterized in that the group represented by the formula: is a group represented by one of the following chemical formulas CY4(1) to CY4(4). [Chemical formula CY4(1)-CY4(4)] In the chemical formulas CY4(1) to CY4(4), A ２１ Or A ２４ , L ３ , Z ２ , Z ３ , and R １０ａ The explanations regarding are the same as those described in claim 1, b22 is an integer from 0 to 2, Ring CY １０ and ring CY １１ are, independently of each other, C ５ -C ３０ Carbocyclic group or C １ -C ３０ is a heterocyclic group, R １１ａ The explanation regarding R １０ａ Please refer to the explanation on b3 and b4 are each independently an integer of 0 to 20, and when b3 is 2 or more, R １０ａ are the same or different from each other, and when b4 is 2 or more, １１ａ are the same or different from each other, *' is a bonding site with M in Chemical Formula 1; *" is a bonding site with an adjacent atom in chemical formula 3.

13. In the above Chemical Formula 3, 【Chemistry 3-(1)】 is a group represented by one of the following chemical formulas CY4(1)-1 to CY4(1)-4, CY4(2)-1 to CY4(2)-4, CY4(3)-1 to CY4(3)-4, and CY4(4)-1. [Chemical formula (CY4(1)-1)-(CY4(1)-4)] [Chemical formula (CY4(2)-1)-(CY4(2)-4)] [Chemical formula (CY4(3)-1)-(CY4(3)-4)] 【Chemistry (CY4(4)-1)】 In the formulae CY4(1)-1 to CY4(1)-4, CY4(2)-1 to CY4(2)-4, CY4(3)-1 to CY4(3)-4, and CY4(4)-1, A ２１ Or A ２４ , L ３ , Z ２ , Z ３ , and R １０ａ The explanations regarding are the same as those described in claim 1, b22 is an integer from 0 to 2, R １１ａ The explanation regarding R １０ａ Please refer to the explanation on b34 and b44 are each independently an integer of 0 to 4, and when b34 is 2 or more, R １０ａ are the same or different from each other, and when b44 is 2 or more, 2 or more R １０ａ are the same or different from each other, b36 is an integer of 0 to 6, and when b36 is 2 or more, R １０ａ are the same or different from each other, *' is a bonding site with M in Chemical Formula 1; *" is a bonding site with an adjacent atom in chemical formula 3.

14. 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.

15. 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; 15. The organic light emitting device of claim 14, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

16. The organic light-emitting device according to claim 14 , wherein the organometallic compound is contained in the light-emitting layer.

17. The organic light emitting device according to claim 16, wherein the light emitting layer emits green light.

18. The light-emitting layer further comprises a host, The organic light emitting device according to claim 16, wherein the content of the host is greater than the content of the organometallic compound.

19. An electronic device comprising the organic light-emitting element according to any one of claims 14 to 18.

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