Organometallic compound and organic light emitting device including the same

Abstract

An organometallic compound represented by the following chemical formula 1, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device are disclosed: M1(L11)n11(L12)n12 L11 in the above Chemical Formula 1 is a ligand represented by the following Chemical Formula 1-1, and For descriptions of other substituents of Chemical Formula 1 and Chemical Formula 1-1, refer to those described in this specification.

Description

Technology Field

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

[0002] Organic light-emitting devices are self-emissive devices that, compared to conventional devices, have a wide viewing angle and excellent contrast, as well as a fast response time, excellent characteristics in brightness, driving voltage and response speed, and are capable of multi-color.

[0003] According to one example, an organic light-emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode, which includes a light-emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state. The problem to be solved

[0004] The invention relates to a novel organometallic compound, an organic light-emitting device employing the same, and an electronic device including the organic light-emitting device. means of solving the problem

[0005] According to one aspect, an organometallic compound represented by the following chemical formula 1 is provided:

[0006] <Chemical Formula 1>

[0007] M1(L 11 ) n11 (L 12 ) n12

[0008] Among the above chemical formula 1,

[0009] M1 is a period 1 transition metal, a period 2 transition metal, or a period 3 transition metal, and

[0010] L 11 is a ligand represented by the following chemical formula 1-1, and

[0011] L 12 is a monodentate or bidentate ligand, and

[0012] n11 is 1, and

[0013] n12 is 0, 1, or 2, and

[0014] <Chemical Formula 1-1>

[0015]

[0016] Among the above chemical formula 1-1,

[0017] *1, *2, *3, and *4 are each binding sites with M1 in the above chemical formula 1, and

[0018] X1 to X4 are independently C or N, and

[0019] The bond between X1 and M1, the bond between X2 and M1, the bond between X3 and M1, and the bond between X4 and M1 are independently covalent bonds or dative bonds, and

[0020] Rings CY1 to CY4 are independent of each other, C5-C 30 Carbocyclic group or C1-C 30 It is a heterocyclic group, and

[0021] T1 to T4 are independently single bonds, *-O-*', *-S-*', *-Se-*', *-S(=O)2-*', *-C(R 50 )(R 60 )-*', *-C(R 50 )=*', *-C(R 50 )=C(R 60 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 50)-*', *-N(R 50 )-*', *-P(R5)-*', *-Si(R 50 )(R 60 )-*', *-P(=O)(R 50 )-*' or *-Ge(R 50 )(R 60 )-*' and,

[0022] a1 to a4 are independently one of integers from 0 to 3, wherein 3 or more of a1 to a4 are independently one of integers from 1 to 3, and

[0023] E1 is a group represented by the following chemical formula 2, and

[0024] n1 to n4 are independently 0, 1, or 2, provided that the sum of n1, n2, n3, and n4 is 1 or greater, and

[0025] <Chemical Formula 2>

[0026]

[0027] Among the above chemical formula 2,

[0028] Gori CY 21 Inner ring CY 23 are independently of each other, C5-C 30 Carbocyclic group or C1-C 30 It is a heterocyclic group, and

[0029] Y 21 is B, P, P(=O) or N, and

[0030] K1 to K3 are independently of each other, single bond, B(R 204 ), N(R 205 ), O, S, Se, C(=O) or S(=O)2 and,

[0031] m1 to m3 are independently 0 or 1, and if m1 is 0, K1 does not exist, if m2 is 0, K2 does not exist, and if m3 is 0, K3 does not exist,

[0032] R 10 , R20 , R 30 , R 40 , R 50 , R 60 and R 201 to R 205 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C1-C 60 Heteroaryloxy groups, substituted or unsubstituted C1-C 60 A heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7) or -P(=O)(Q8)(Q9), and

[0033] c10, c20, c30, and c40 are independently one of integers from 1 to 10, and

[0034] c201 to c203 are independently one of integers 1 to 10, and

[0035] The above-mentioned substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C1-C 60 Heteroaryloxy group, substituted C1-C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are,

[0036] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof or phosphate group or salt thereof;

[0037] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic 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 ) or substituted or unsubstituted by any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxygenation;

[0038] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ) or substituted or unsubstituted with any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

[0039] -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ) or -P(=O)(Q 38 )(Q 39 ); or

[0040] Any combination of these; and,

[0041] The above Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0042] According to another aspect, an organic light-emitting device is provided, 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, wherein the organic layer includes one or more organometallic compounds.

[0043] According to another aspect, an electronic device including the above-mentioned organic light-emitting element is provided. Effects of the invention

[0044] An organic light-emitting device containing an organometallic compound represented by the above chemical formula 1 can have high efficiency and improved color purity. Brief explanation of the drawing

[0045] FIG. 1 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment. FIG. 2 is a diagram showing the PL (Photoluminescence) spectra of a compound according to one embodiment and a comparative compound, respectively. Specific details for implementing the invention

[0046] An organometallic compound according to one embodiment can be represented by the following chemical formula 1:

[0047] <Chemical Formula 1>

[0048] M1(L 11 ) n11 (L 12 ) n12

[0049] In the above chemical formula 1, M1 may be a first-period transition metal, a second-period transition metal, or a third-period transition metal.

[0050] For example, M1 in the above chemical formula 1 may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), palladium (Pd), or gold (Au).

[0051] According to one embodiment, M1 in the above chemical formula 1 may be Pt, Pd, or Au.

[0052] For example, M1 in the above chemical formula 1 may be Pt.

[0053] L in the above Chemical Formula 1 11 It may be a ligand represented by the following chemical formula 1-1.

[0054] In the above chemical formula 1, n11 can be 1.

[0055] L in the above Chemical Formula 1 12 It can be a monodentate ligand or a bidentate ligand.

[0056] In the above Chemical Formula 1, n12 can be 0, 1, or 2. If n12 is 2, 2 L 12 They may be the same or different from each other.

[0057] According to one embodiment, in the above Chemical Formula 1, L 12may be a ligand represented by any one of the following chemical formulas 8-1 to 8-23, but is not limited thereto:

[0058]

[0059]

[0060]

[0061] Among the above chemical formulas 8-1 to 8-23,

[0062] pH is a phenyl group;

[0063] Ph-d5 is a phenyl group in which all hydrogens are substituted with deuterium;

[0064] * and *' are bonding sites with neighboring atoms.

[0065] According to one embodiment, in the above chemical formula 1, M1 may be Pt, n11 may be 1, and n12 may be 0, but is not limited thereto.

[0066] <Chemical Formula 1-1>

[0067]

[0068] In the above chemical formula 1-1, *1, *2, *3, and *4 are each binding sites with M1 in the above chemical formula 1.

[0069] In the above chemical formula 1-1, X1 to X4 may be C or N independently of each other.

[0070] The bond between X1 in Chemical Formula 1-1 and M1 in Chemical Formula 1, the bond between X2 in Chemical Formula 1-1 and M1 in Chemical Formula 1, the bond between X3 in Chemical Formula 1-1 and M1 in Chemical Formula 1, and the bond between X4 in Chemical Formula 1-1 and M1 in Chemical Formula 1 are independently covalent bonds or dative bonds.

[0071] According to one embodiment, two of the bonds between X1 in Formula 1-1 and M1 in Formula 1, between X2 in Formula 1-1 and M1 in Formula 1, between X3 in Formula 1-1 and M1 in Formula 1, and between X4 in Formula 1-1 and M1 in Formula 1 may be coordinate bonds, and the remaining two may be covalent bonds. Thus, the organometallic compound represented by Formula 1 may be electrically neutral.

[0072] According to one embodiment, the bond between X1 in Chemical Formula 1-1 and M1 in Chemical Formula 1 may be a coordinate bond.

[0073] For example, X1, X2, and X3 are each C, and X4 is N, and the bond between X2 and M1 and the bond between X3 and M1 are covalent bonds, and the bond between X1 and M1 and the bond between X4 and M1 may be coordinate bonds.

[0074] In the above chemical formula 1-1, rings CY1 to CY4 are independently of each other, C5-C 30 Carbocyclic group or C1-C 30 It can be a heterocyclic group.

[0075] According to one embodiment, the rings CY1 to CY4 in the above formula 1-1 are independently of each other i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed together, iv) a condensed ring in which two or more second rings are condensed together, or v) a condensed ring in which one or more first rings and one or more second rings are condensed together.

[0076] The first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silol group, a borol group, a phosphol group, a germol group, a selenophene group, an oxazole group, an isoxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, an isothiaazole group, a thiadiazole group, a thiatriazole group, a pyrazol group, an imidazole group, a triazole group, a tetrazole group, an azacilol group, a diazcilol group, or a triazcilol group, and

[0077] The second ring above may be an adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, cyclohexadiene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, oxazine group, thiazine group, dihydropyrazine group, dihydropyridine group, or dihydroazacilol group.

[0078] According to another embodiment, ring CY1 to ring CY4 in Formula 1-1 are independently a cyclopentane group, a cyclopentene group, a cyclohexane group, a cyclohexene group, a cyclohexadiene group, a benzene group, a naphthalene group, anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, a thiophene group, a furan group, a borol group, a phosphol group, a germolar group, a selenophene group, an indole group, a benzoborol group, a benzophospol group, an indene group, a benzosilol group, a benzozermolar group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborol group, a dibenzophospol group, a fluorene group, Dibenzocillol group, dibenzozermol group, dibenzothiophen group, dibenzoselenopene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborol group, azabenzophospol group, azaindene group, azabenzocillol group, azabenzozermol group, azabenzothiophene group, azabenzoselenopene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophospol group, azafluoren group, azadibenzocillol group, azadibenzozermol group, azadibenzothiophene group, azadibenzoselenopene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, Aza-9H-fluoren-9-one group, azadibenzothiophen 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazol group, imidazole group, triazole group, oxazole group, isooxazole group, thiazole group, isothiaazole group, oxadiazole group, thiadiazole group, benzopyrazol group, benzimidazole group, benzoxazole group, benzothiaazole group,It may be a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0079] According to one embodiment, a1 in the above formula 1-1 is not 0, and the ring CY1 may be a group represented by one of the following formulas CY1(1) to CY1(56) and CY1(101) to CY1(108).

[0080]

[0081]

[0082]

[0083]

[0084] Among the above chemical formulas CY1(1) to CY1(56) and CY1(101) to CY1(108),

[0085] X1 is C or N, wherein X1 is C among the above chemical formulas CY1 (27) to CY1 (39) and CY1 (101) to CY1 (108), and

[0086] X 11 is O, S, N(R 18 ), C(R 18 )(R 19 ) or Si(R 18 )(R 19 ) and, the above R 18 and R 19 Descriptions of each of R in this specification 10 Refer to the explanation for,

[0087] * is the binding site with M1 in the above chemical formula 1, and

[0088] *' is the binding site with T1 in the above chemical formula 1-1, and

[0089] *" is the binding site with T4 in the above chemical formula 1.

[0090] According to one embodiment, in the above formula 1-1, a1 is not 0 and a2 is not 0, and the ring CY2 may be a group represented by one of the following formulas CY2(1) to CY2(15):

[0091]

[0092] Among the above chemical formulas CY2(1) to CY2(15),

[0093] X2 is C or N, and

[0094] X 21 is O, S, N(R 28 ), C(R 28 )(R 29 ) or Si(R 28 )(R 29 ) and, the above R 28 and R 29 Descriptions of each of R in this specification 20 Refer to the explanation for,

[0095] * is the binding site with M1 in the above chemical formula 1, and

[0096] *' is the binding site with T1 in the above chemical formula 1-1, and

[0097] *" is the binding site with T2 in the above chemical formula 1-1.

[0098] According to one embodiment, in the above formula 1-1, a2 is not 0, a3 is not 0, and the ring CY3 may be a group represented by the following formula CY3-A or CY3-B:

[0099]

[0100] Among the above chemical formulas CY3-A and CY3-B,

[0101] Refer to the descriptions of X3 and ring CY3 as set forth in this specification, respectively.

[0102] Y 31 and Y 33 are independently C or N, and Y 32 is O, S, N, C, or Si, and

[0103] X3 and Y in the above chemical formula CY3-A 33 The combination between X3 and Y 32 The connection between and Y 32 and Y 31 The bonds between them are each chemical bonds (e.g., single bonds or double bonds), and X3 and Y in the above chemical formula CY3-B 31 The combination between and X3 and Y 33 The bonds between them are each chemical bonds (e.g., single bonds or double bonds), and

[0104] * is the binding site with M1 in the above chemical formula 1, and

[0105] *" is the binding site with T2 in the above chemical formula 1-1, and

[0106] *' may be a binding site with T3 in the above chemical formula 1.

[0107] According to another embodiment, in the above formula 1-1, a2 is not 0 and a3 is not 0, and the ring CY3 may be a group represented by one of the following formulas CY3(1) to CY3(12) and CY3(101) to CY3(122):

[0108]

[0109]

[0110]

[0111] Among the above chemical formulas CY3(1) to CY3(12) and CY3(101) to CY3(122),

[0112] X3 is C or N, and

[0113] X 31 single bond, O, S, N(R 38 ), C(R 38)(R 39 ) or Si(R 38 )(R 39 ) and, X 32 is O, S, N(R 38 ), C(R 38 )(R 39 ) or Si(R 38 )(R 39 ) and, the above R 38 and R 39 Descriptions of each of R in this specification 30 Refer to the explanation for,

[0114] * is the binding site with M1 in the above chemical formula 1, and

[0115] *" is the binding site with T2 in the above chemical formula 1-1, and

[0116] *' is the binding site with T3 in the above chemical formula 1-1.

[0117] According to another embodiment, in the above chemical formula 1-1, a2 is not 0 and a3 is not 0, The group represented by may be a group represented by one of the following chemical formulas CY3-1 to CY3-20:

[0118]

[0119]

[0120]

[0121] Among the above chemical formulas CY3-1 to CY3-20,

[0122] X3 is C or N, and

[0123] X 31 single bond, O, S, N(R 38 ), C(R 38 )(R 39 ) or Si(R 38 )(R 39 ) and, X 32 is O, S, N(R 38 ), C(R 38 )(R 39) or Si(R 38 )(R 39 ) and, the above R 38 and R 39 Descriptions of each of R in this specification 30 Refer to the explanation for,

[0124] For a description of E1, refer to the description in this specification, and

[0125] E 1a and E 1b For a description of each, refer to the description of E1 in this specification, and said E 1a and E 1b are identical or different from each other,

[0126] * is the binding site with M1 in the above chemical formula 1, and

[0127] *" is the binding site with T2 in the above chemical formula 1-1, and

[0128] *' is the binding site with T3 in the above chemical formula 1-1.

[0129] According to one embodiment, a3 in the above formula 1-1 is not 0, and the ring CY4 may be a group represented by one of the following formulas CY4(1) to CY4(42) and CY4(101) to CY4(111):

[0130]

[0131]

[0132]

[0133]

[0134] Among the above chemical formulas CY4(1) to CY4(42) and CY4(101) to CY4(111),

[0135] X4 is C or N, and

[0136] X 41 is O, S, N(R 48 ), C(R 48 )(R 49) or Si(R 48 )(R 49 ) and, X 42 is a single bond, O, S, N(R 48 ), C(R 48 )(R 49 ) or Si(R 48 )(R 49 ) and, the above R 48 and R 49 Descriptions of each of R in this specification 40 Refer to the explanation for,

[0137] * is the binding site with M1 in the above chemical formula 1, and

[0138] *' is the binding site with T3 in the above chemical formula 1-1, and

[0139] *" is the binding site with T4 in the above chemical formula 1-1.

[0140] In the above chemical formula 1-1, T1 to T4 are independently single bonds, *-O-*', *-S-*', *-Se-*', *-S(=O)2-*', *-C(R 50 )(R 60 )-*', *-C(R 50 )=*', *-C(R 50 )=C(R 60 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 50 )-*', *-N(R 50 )-*', *-P(R5)-*', *-Si(R 50 )(R 60 )-*', *-P(=O)(R 50 )-*' or *-Ge(R 50 )(R 60 )-*'can be.

[0141] In the above chemical formula 1-1, a1 to a4 are independently one of integers from 0 to 3, and 3 or more of a1 to a4 are independently one of integers from 1 to 3. That is, the organometallic compound represented by the above chemical formula 1 may have a tetradentate ligand.

[0142] If a1 is 0, T1 does not exist, if a2 is 0, T2 does not exist, if a3 is 0, T3 does not exist, and if a4 is 0, T4 does not exist.

[0143] According to one embodiment, in the above formula 1-1, i) a1 is 0 and a2, a3, and a4 are independently integers from 1 to 3, ii) a2 is 0 and a1, a3, and a4 are independently integers from 1 to 3, iii) a3 is 0 and a1, a2, and a4 are independently integers from 1 to 3, or iv) a4 is 0 and a1, a2, and a3 are independently integers from 1 to 3.

[0144] According to one embodiment, in the above chemical formula 1-1, a1 is not 0 and T1 may be a single bond.

[0145] According to one embodiment, in the above chemical formula 1-1, a2 is not 0, and T2 is *-O-*', *-S-*', *-C(R 50 )(R 60 )-*', *-B(R 50 )-*', *-N(R 50 )-*', *-P(R5)-*', *-Si(R 50 )(R 60 )-*' or *-Ge(R 50 )(R 60 )-*'can be.

[0146] According to one embodiment, in the above Chemical Formula 1-1, a3 is not 0, and T3 is a single bond, *-O-*', *-S-*', *-C(R 50 )(R60 )-*', *-B(R 50 )-*', *-N(R 50 )-*', *-P(R5)-*', *-Si(R 50 )(R 60 )-*' or *-Ge(R 50 )(R 60 )-*'can be.

[0147] According to one embodiment, a4 in the above chemical formula 1-1 may be 0.

[0148] E1 in the above chemical formula 1-1 may be a group represented by the following chemical formula 2:

[0149] In the above chemical formula 1-1, n1 to n4 each represent the number of E1s, which are independently 0, 1, or 2, provided that the sum of n1, n2, n3, and n4 is 1 or more. That is, the organometallic compound represented by the above chemical formula 1 includes at least one group represented by the following chemical formula 2.

[0150] For example, the sum of n1, n2, n3, and n4 in the above chemical formula 1-1 may be 1.

[0151] As another example, in the above chemical formula 1-1, n1, n2, and n4 may each be 0, and n3 may be 1.

[0152] <Chemical Formula 2>

[0153]

[0154] The above chemical formula 2 double ring CY 21 Inner ring CY 23 are independently of each other, C5-C 30 Carbocyclic group or C1-C 30 It can be a heterocyclic group.

[0155] According to one embodiment, the double ring CY of formula 2 above 21 Inner ring CY 23They may be independently a benzene group, a naphthalene group, anthracene group, phenanthrene group, pyrene group, furan group, thiophene group, pyrrole group, cyclopentene group, silol group, germolar group, benzofuran group, benzothiophene group, indole group, indene group, benzocilol group, benzozermolar group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dibenzocilol group, dibenzozermolar group, indolodibenzofuran group, indolodibenzothiophene group, indolocarbazole group, indolofluorene group, indolodibenzocilol group, or indolodibenzozermolar group.

[0156] Y in the above chemical formula 2 21 can be B, P, P(=O) or N.

[0157] According to one embodiment, Y in the above chemical formula 2 21 It can be B or N.

[0158] In the above chemical formula 2, K1 to K3 are independently single bonds, B(R 204 ), N(R 205 ), O, S, Se, C(=O) or S(=O)2 can be.

[0159] According to one embodiment, among the above chemical formula 2,

[0160] i) Y 21 is B, and K1 to K3 are each O or;

[0161] ii) Y 21 is B, and K1 to K3 are each N(R 205 ) or;

[0162] iii) Y 21 is B, at least one of K1 to K3 is O, and at least one of K1 to K3 is N(R 205 ) or;

[0163] iv) Y 21 is N, and K1 to K3 are each single bonds or;

[0164] v) Y21 is N, and K1 to K3 are each C(=O) or,

[0165] vi) Y 21 is N, and K1 to K3 can each be S(=O)2.

[0166] In the above chemical formula 2, m1 to m3 are independently 0 or 1, and when m1 is 0, K1 does not exist, when m2 is 0, K2 does not exist, and when m3 is 0, K3 does not exist.

[0167] According to one embodiment, the sum of m1, m2 and m3 may be 2 or 3.

[0168] For example, i) m1, m2, and m3 may each be 1, ii) m1 and m3 may each be 1 and m2 may be 0, iii) m1 and m2 may each be 1 and m3 may be 0, or iv) m2 and m3 may each be 1 and m1 may be 0.

[0169] According to another embodiment, E1 in Formula 1-1 may be a group represented by any one of the following Formulas 2-1 to 2-8:

[0170]

[0171]

[0172] Among the above chemical formulas 2-1 to 2-8,

[0173] R 206 and R 207 Descriptions of each of R in this specification 201 Refer to the explanation for,

[0174] c201 and c206 are one of integers 1 to 3, and

[0175] c202, c203, and c207 are one of integers 1 to 4, and

[0176] Y 21 , K1 to K3 and R 201 to R 203For descriptions of each, refer to the descriptions in this specification, and

[0177] * is a bonding site with a neighboring atom.

[0178] Among the above chemical formulas 1-1 and 2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 and R 201 to R 205 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C1-C 60 Heteroaryloxy groups, substituted or unsubstituted C1-C 60It may be a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7) or -P(=O)(Q8)(Q9).

[0179] In the above chemical formula 1-1, c10, c20, c30, and c40 are independently one of integers from 1 to 10, and in the above chemical formula 2, c201 to c203 may be independently one of integers from 1 to 10.

[0180] According to another embodiment, among the above chemical formulas 1-1 and 2, R 10 , R 20 , R 30 , R 40 , R 50 , R 60 and R 201 to R 205 s / g

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209] The above Q1 to Q9 are independent of each other,

[0210] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or

[0211] Deuterium, C1-C 10 n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, or naphthyl group, substituted or unsubstituted with at least one selected from alkyl groups and phenyl groups;

[0212] And,

[0213] Among the above chemical formulas 9-1 to 9-26 and 10-1 to 10-256,

[0214] * is a bonding site with a neighboring atom, and

[0215] i-Pr is an isopropyl group, t-Bu is a t-butyl group, and

[0216] pH is a phenyl group, and

[0217] 1-Nph is a 1-naphthyl group, and 2-Nph is a 2-naphthyl group, and

[0218] 2-Pyr is a 2-pyridyl group, 3-Pyr is a 3-pyridyl group, 4-Pyr is a 4-pyridyl group, and

[0219] TMS is a trimethylsilyl group.

[0220] According to one embodiment, the organometallic compound may be represented by any one of the following chemical formulas 1-1A to 1-1E:

[0221] <Chemical Formula 1-1A>

[0222]

[0223] <Chemical Formula 1-1B>

[0224]

[0225] <Chemical Formula 1-1C>

[0226]

[0227] <Chemical Formula 1-1D>

[0228]

[0229] <Chemical Formula 1-1E>

[0230]

[0231] In the above chemical formulas 1-1A and 1-1B, X1 is C, and X2 to X4 are independently C or N, and

[0232] In the above chemical formulas 1-1C to 1-1E, X1 to X4 are independently C or N, and

[0233] Among the above chemical formulas 1-1A to 1-1E, Z 11 To Z 15 are independent of each other, R 10 or E1 and Z 21 To Z 23 are independent of each other, R 20 or E1 and Z 31 To Z 36 are independent of each other, R 30 or E1 and Z 41 To Z 44 are independent of each other, R 40 or E1 and,

[0234] Z in the above chemical formulas 1-1A and 1-1E 11 To Z 15 , Z 21 To Z 23 , Z 31 To Z 36 and Z 41 To Z 44 At least one of them is E1, and

[0235] Z in the above chemical formulas 1-1B to 1-1D 11 To Z 13 , Z 21 To Z 23 , Z 31 To Z 36 and Z41 To Z 44 At least one of them is E1, and

[0236] M1, T2, R 10 , R 20 , R 30 , R 40 For descriptions of and E1, refer to the descriptions in this specification.

[0237] According to one embodiment, Z in the above formulas 1-1A and 1-1E 11 To Z 15 are respectively R 10 Igo, Z 11 To Z 15 are identical or different from each other, and Z among the above chemical formulas 1-1B to 1-1D 11 To Z 13 are respectively R 10 Igo, Z 11 To Z 13 They may be the same or different from each other.

[0238] According to one embodiment, among the above formulas 1-1A to 1-1E, Z 21 To Z 23 are respectively R 20 Igo, Z 21 To Z 23 They may be the same or different from each other.

[0239] According to one embodiment, among the above formulas 1-1A to 1-1E, Z 31 To Z 33 , Z 35 and Z 36 are respectively R 30 Igo, Z 31 To Z 33 , Z 35 and Z 36 They may be the same or different from each other.

[0240] According to one embodiment, among the above formulas 1-1A to 1-1E, Z 34 It can be E1.

[0241] According to one embodiment, among the above formulas 1-1A to 1-1E, Z 41 To Z 44 are respectively R 40 Igo, Z 41 To Z 44 They may be the same or different from each other.

[0242] The above-mentioned substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C1-C 60 Heteroaryloxy group, substituted C1-C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heterocondensed polycyclic group are,

[0243] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof or phosphate group or salt thereof;

[0244] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic 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 ) or substituted or unsubstituted by any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxygenation;

[0245] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ) or substituted or unsubstituted with any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

[0246] -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ) or -P(=O)(Q 38 )(Q 39 ); or

[0247] Any combination of these; and,

[0248] The above Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0249] According to one embodiment, the organometallic compound may be any one of the following compounds Pt-1 to Pt-63, but is not limited thereto.

[0250]

[0251] The organometallic compound represented by the above chemical formula 1 includes at least one group represented by chemical formula 2 as a substituent, so that the local excited state of the ligand ( 3The LC) energy can be stabilized. Accordingly, when the organometallic compound emits light, 3 The contribution of luminescence from LC is increased, so that the intensity of the second emission peak of the luminescence spectrum of the organometallic compound decreases, and thus the color purity can be improved.

[0252] In addition, the organometallic compound represented by Chemical Formula 1 may include at least one group represented by Chemical Formula 2, so that intermolecular aggregation can be substantially suppressed. Accordingly, the quenching phenomenon of the organometallic compound is substantially suppressed, and thus the efficiency and lifespan of the organic light-emitting device containing the organometallic compound can be improved. Furthermore, the organometallic compound represented by Chemical Formula 1 may include at least one group represented by Chemical Formula 2, so that the formation of intermolecular exciplexes and excimers can be substantially suppressed. Accordingly, the color purity of the organic light-emitting device containing the organometallic compound can be improved.

[0253] A method for synthesizing an organometallic compound represented by the above chemical formula 1 can be recognized by those skilled in the art by referring to the synthesis examples described below.

[0254] The results of evaluating the HOMO energy level, LUMO energy level, T1 energy level, decay time (τ), and full width at half maximum (FWHM) of the compound according to one embodiment and comparative compounds C1 and C2 among the organometallic compounds represented by Chemical Formula 1 above using a Gaussian 09 program accompanied by molecular structure optimization based on density functional theory (DFT) based on B3LYP are as shown in Table 1 below.

[0255] Compound No. HOMO(eV) LUMO(eV) T1(eV) Tau(τ)(μs) FWHM(nm) Maximum emission wavelength (λ max )(nm) Pt-1 -4.72 -1.65 2.66 0.58 28 461 Pt-2 -4.67 -1.63 2.68 0.99 27 458 Pt-3 -4.63 -1.62 2.67 0.88 27 459 Pt-4 -4.70 -1.52 2.66 0.54 29 461 Pt-5 -4.65 -1.50 2.70 0.91 27 459 Pt-6 -4.62 -1.50 2.69 0.77 27 456 Pt-7 -4.70 -1.60 2.66 0.57 28 461 Pt-8 -4.65 -1.58 2.69 0.95 26 456 Pt-9 -4.61 -1.57 2.68 0.79 27 457 Pt-25 -4.68 -1.26 2.66 0.54 29 460 Pt-26 -4.66 -1.23 2.66 0.56 28 461 Pt-46 -4.86 -1.68 2.70 1.53 15 455 Pt-47 -4.75 -1.54 2.70 0.76 20 455 Pt-48 -4.66 -1.63 2.60 1.07 50 469 Pt-49 -4.64 -1.50 2.60 1.05 50 470 Pt-50 -4.67 -1.63 2.58 1.16 52 473 Pt-51 -4.65 -1.50 2.57 1.16 53 473 C1 -4.65 -1.22 2.65 0.58 32 461 C2 -4.43 -1.59 1.91 3.72 41 648

[0256] <Compound C1>

[0257]

[0258] <Compound C2>

[0259]

[0260] From Table 1 above, it can be confirmed that the organometallic compound according to one embodiment has a higher T1 energy level and a blue shift in maximum emission wavelength compared to comparative compound C2, and has electrical characteristics suitable for use as an emissive layer material for an organic light-emitting device, for example, as a blue light-emitting material.

[0261] Accordingly, according to another aspect, an organic light-emitting device is provided 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, wherein the organic layer includes one or more organometallic compounds as described above.

[0262] The above-described organic light-emitting device can have a low driving voltage, high efficiency, high brightness, high quantum efficiency, and / or a long lifespan by having an organic layer containing an organometallic compound as described above.

[0263] In this specification, the phrase “(the organic layer) comprises one or more organometallic compounds” may be interpreted as “(the organic layer) may comprise one organometallic compound belonging to the category of Formula 1 or two or more different organometallic compounds belonging to the category of Formula 1.”

[0264] For example, the organic layer may include only compound 1 as the organometallic compound. In this case, compound 1 may be present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may include compound 1 and compound 2 as the organometallic compound. In this case, compound 1 and compound 2 may be present in the same layer (for example, both compound 1 and compound 2 may be present in the light-emitting layer).

[0265] According to one embodiment, one or more organometallic compounds may be included in the light-emitting layer of the organic light-emitting device.

[0266] One or more organometallic compounds included in the above-mentioned light-emitting layer can act as emitters. For example, a light-emitting layer containing one or more organometallic compounds represented by Chemical Formula 1 can emit phosphorescence generated as the triplet excitons of the organometallic compounds transition to the ground state.

[0267] For example, the emitting layer of the organic light-emitting device comprises a host and a dopant, and the dopant may comprise one or more organometallic compounds. The host may be selected from any host. That is, the organometallic compound may act as a dopant. The emitting layer may emit blue light having a maximum emission wavelength of about 440 nm to about 480 nm, for example, about 440 nm to 470 nm.

[0268] According to another embodiment, the light-emitting layer comprises a host and a dopant, wherein the host is selected from any host, the dopant comprises an organometallic compound represented by Chemical Formula 1, and the light-emitting layer may further comprise a fluorescent dopant. The light-emitting layer may emit fluorescence generated as the triplet exciton of the organometallic compound is transferred to and then transferred to the fluorescent dopant.

[0269] The first electrode may be an anode that is a hole injection electrode and the second electrode may be a cathode that is an electron injection electrode, or the first electrode may be a cathode that is an electron injection electrode and the second electrode may be an anode that is a hole injection electrode.

[0270] According to one embodiment, the first electrode is an anode and the second electrode is a cathode, and the organic layer 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, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0271] For example, the organometallic compound may be included in at least one of the hole transport region and the electron transport region.

[0272] Description of Fig. 1

[0273] FIG. 1 schematically illustrates a cross-sectional view of an organic light-emitting element (10) according to one embodiment of the present invention. Hereinafter, the structure and manufacturing method of an organic light-emitting element according to one embodiment of the present invention will be described with reference to FIG. 1 as follows.

[0274] The organic light-emitting element (10) of FIG. 1 has a structure in which a first electrode (11), an organic layer (15), and a second electrode (19) are stacked in sequence.

[0275] A substrate may be additionally disposed on the lower part of the first electrode (11) or on the upper part of the second electrode (19). As the substrate, a substrate used in conventional organic light-emitting diodes may be used, and a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance may be used.

[0276] The first electrode (11) can be formed, for example, by providing a material for the first electrode on a substrate using a deposition method or a sputtering method. The first electrode (11) may be an anode. The material for the first electrode may be selected from materials having a high work function to facilitate hole injection.

[0277] The first electrode (11) may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. For the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. may be used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used.

[0278] The first electrode (11) may have a single layer or a multilayer structure including two or more layers. For example, the first electrode (11) may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0279] An organic layer (15) is disposed above the first electrode (11).

[0280] The above organic layer (15) may include a hole transport region; an emission layer; and an electron transport region.

[0281] The above hole transport region can be placed between the first electrode (11) and the light-emitting layer.

[0282] The hole transport region above may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

[0283] The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode (11).

[0284] If the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode (11) using various methods such as vacuum deposition, spin coating, casting, LB method, etc.

[0285] When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but for example, a deposition temperature of about 100 to about 500°C and a vacuum degree of about 10 -8 to about 10 -3 torr, deposition rate can be selected in the range of about 0.01 to about 100 Å / sec, but is not limited thereto.

[0286] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, but a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature for solvent removal after coating can be selected in a temperature range of about 80°C to 200°C, but are not limited thereto.

[0287] The above conditions for forming the hole transport layer and electron blocking layer refer to the conditions for forming the hole injection layer.

[0288] The above hole transport region is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphorsulfonic acid), PANI / PSS (Polyaniline) / Poly(4-styrenesulfonate):Polyaniline) / Poly(4-styrenesulfonate)), may include at least one of a compound represented by the following chemical formula 201 and a compound represented by the following chemical formula 202:

[0289]

[0290]

[0291] <Chemical Formula 201>

[0292]

[0293] <Chemical Formula 202>

[0294]

[0295] In the above chemical formula 201, Ar 101 and Ar 102 are independently, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl group, C2-C60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 It may be a phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, naphthacenylene group, pisenylene group, perylenylene group, or pentacenylene group, 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.

[0296] In the above chemical formula 201, xa and xb may independently be integers from 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

[0297] Among the above chemical formulas 201 and 202, R 101 to R 108 , R 111 to R 119 and R 121 to R 124 are independently of each other,

[0298] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 10Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) or C1-C 10 Alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.);

[0299] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt and phosphoric acid or its salt, or any combination thereof, substituted or unsubstituted with, C1-C 10 alkyl group or C1-C 10 Alkoxy group; or

[0300] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 10 Alkyl group, C1-C 10 A phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group substituted or unsubstituted with an alkoxy group, or any combination thereof;

[0301] It could be.

[0302] R in the above chemical formula 201 109 is, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 20 Alkyl group, C1-C 20 It may be a phenyl group, naphthyl group, anthracenyl group, or pyridinyl group substituted or unsubstituted with an alkoxy group, a phenyl group, a naphthyl group, anthracenyl group, a pyridinyl group, or any combination thereof.

[0303] According to one embodiment, the compound represented by the above chemical formula 201 may be represented by the following chemical formula 201A:

[0304] <Chemical Formula 201A>

[0305]

[0306] In the above chemical formula 201A, R 101 , R 111 , R 112 and R 109 For a detailed explanation of [this], refer to the above.

[0307] For example, the hole transport region may include one of the following compounds HT1 to HT20 or any combination thereof:

[0308]

[0309]

[0310]

[0311]

[0312] The thickness of the hole transport region may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about 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 may be 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 ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0313] In addition to the material described above, the hole transport region may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

[0314] The charge-generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinone dimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ), F6-TCNNQ, etc.; metal oxides such as tungsten oxide and molybdenum oxide, etc.; and cyano group-containing compounds such as the following compounds HT-D1, HT-D2, etc., but are not limited thereto.

[0315]

[0316]

[0317] The above hole transport region may further include a buffer layer.

[0318] The above buffer layer can play a role in increasing efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light-emitting layer.

[0319] A light-emitting layer can be formed on the above hole transport region using methods such as vacuum deposition, spin coating, casting, and LB methods. When forming a light-emitting layer by vacuum deposition and spin coating, the deposition and coating conditions vary depending on the compound used, but generally, they can be selected from a range of conditions that are almost identical to those for forming a hole injection layer.

[0320] The hole transport region may further include an electron blocking layer. The electron blocking layer may include known materials, for example, mCP, but is not limited thereto.

[0321]

[0322] The thickness of the electron blocking layer may be about 50 Å to about 1000 Å, for example, about 70 Å to about 500 Å. When the thickness of the electron blocking layer satisfies the range described above, satisfactory electron blocking characteristics can be obtained without a substantial increase in driving voltage.

[0323] When the above organic light-emitting device is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer. Alternatively, various variations are possible, such as the light-emitting layer having a stacked structure of a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer to emit white light.

[0324] The light-emitting layer may include an organometallic compound represented by the chemical formula 1.

[0325] The light-emitting layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Chemical Formula 1.

[0326] The above host may include the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof:

[0327]

[0328]

[0329]

[0330] Alternatively, the host may further include a compound represented by the following chemical formula 301:

[0331] <Chemical Formula 301>

[0332]

[0333] In the above chemical formula 301, Ar 111 and Ar 112 are independently of each other,

[0334] Phenylene group, naphthylene group, phenanthrenylene group or pyrenylene group; or

[0335] It may be a phenylene group, a naphthylene group, a phenanthrenylene group and a pyrenylene group substituted with a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof.

[0336] Among the above chemical formula 301, the Ar 113 or Ar 116 are independently of each other,

[0337] C1-C 10 Alkyl group, phenyl group, naphthyl group, phenanthrenyl group or pyrenyl group; or

[0338] It may be a phenyl group, naphthyl group, phenanthrenyl group, or pyrenyl group substituted with a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof.

[0339] In the above chemical formula 301, g, h, i, and j may independently be 0, 1, 2, 3, or 4, for example, 0, 1, or 2.

[0340] In the above chemical formula 301, Ar 113 or Ar 116 are independently of each other,

[0341] C1-C substituted with a phenyl group, a naphthyl group, anthracenyl group, or any combination thereof 10 Alkyl group;

[0342] Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, or fluorenyl group;

[0343] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60A phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, fluorenyl group, or fluorenyl group substituted with an alkoxy group, a phenyl group, a naphthyl group, a naphthyl group, a pyrenyl group, a phenanthrenyl group, or any combination thereof; or

[0344] It may be, but is not limited to this.

[0345] Alternatively, the host may include a compound represented by the following chemical formula 302:

[0346] <Chemical Formula 302>

[0347]

[0348] Ar in the above chemical formula 302 122 or Ar 125 A detailed explanation of Ar in the above chemical formula 301 is provided. 113 Refer to the explanation for.

[0349] Ar in the above chemical formula 302 126 and Ar 127 are independently of each other, C1-C 10 It may be an alkyl group (e.g., methyl group, ethyl group, or propyl group).

[0350] In the above chemical formula 302, k and l may be integers 0, 1, 2, 3, or 4 independently of each other. For example, k and l may be 0, 1, or 2.

[0351] When the above organic light-emitting device is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer. Alternatively, various variations are possible, such as the light-emitting layer having a stacked structure of a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer to emit white light.

[0352] When the light-emitting layer includes a host and a dopant, the content of the dopant may be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the light-emitting layer, but is not limited thereto. If the content of the dopant satisfies the above range, light emission without quenching phenomenon may be achieved.

[0353] According to one embodiment, the organic layer of the organic light-emitting device may further include a fluorescent dopant in addition to the organometallic compound represented by Chemical Formula 1.

[0354] For example, the fluorescent dopant may be a condensed polycyclic compound, a styryl compound, or any combination thereof.

[0355] According to one embodiment, the fluorescent dopant may be a compound represented by the following chemical formula 501:

[0356] <Chemical Formula 501>

[0357]

[0358] Among the above chemical formula 50,

[0359] Ar 501 silver

[0360] Naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, fisene, perylene, pentafene, indenoanthracene, tetracene, bisanthracene, or the group represented by the above chemical formulas 501-1 to 501-18; or

[0361] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ) (Above Q 501 to Q 503 They are independently of each other, hydrogen, C1-C 60 Alkyl group, C1-C 60 Alkoxy group, C6-C 60 Aryl group, C1-C 60 Naphthalene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, fisene, perylene, pentafene, indenoanthracene, tetracene, bisanthracene, or a group represented by the above formulas 501-1 to 501-18, substituted with a heteroaryl group, a monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group), or any combination thereof; and

[0362] L 501 to L 503 C3-C independently of each other, substituted or unsubstituted 10 Cycloalkylene group, substituted or unsubstituted C1-C 10 Heterocycloalkylene groups, substituted or unsubstituted C3-C 10 Cycloalkenylene group, substituted or unsubstituted C1-C 10 Heterocycloalkenylene groups, substituted or unsubstituted C6-C 60 Aryllene group, substituted or unsubstituted C1-C 60A heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group or a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group, and

[0363] R 501 and R 502 are independently of each other,

[0364] Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, triazinyl group, dibenzofuranyl group or dibenzothiophenyl group; or

[0365] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazoleyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, or any combination thereof substituted with, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflurenyl group, dibenzoflurenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, Pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazoleyl group, triazinyl group, dibenzofuranyl group or dibenzothiophenyl group; and,

[0366] xd1 to xd3 are independently 0, 1, 2, and 3, and

[0367] xd4 is 0, 1, 2, 3, 4, 5 or 6.

[0368] For example, among the above chemical formula 50,

[0369] Ar 501 silver

[0370] Naphthalene, fluorene, spiro-bifluorene, benzofluorene, dibenzofluorene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, fisene, perylene, pentafene, indenoanthracene, tetracene, bisanthracene, or the group represented by the above chemical formulas 501-1 to 501-18; or

[0371] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazoleyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group and -Si(Q 501 )(Q 502 )(Q 503 ) (Above Q 501 to Q 503 They are independently of each other, hydrogen, C1-C 20 Alkyl group, C1-C 20 Naphthalene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, fisene, perylene, pentapene, indenoanthracene, tetracene, bisanthracene, or a group represented by the above formulas 501-1 to 501-18, substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group) or any combination thereof; and

[0372] L 501 to L 503 The description of L in this specification 21 Refer to the explanation for,

[0373] xd1 to xd3 are independently 0, 1, or 2, and

[0374] xd4 can be 0, 1, 2 or 3, but is not limited thereto.

[0375] The fluorescent dopant may include, for example, the following compounds FD(1) to FD(16), FD1 to FD13, or any combination thereof:

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384] The thickness of the light-emitting layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0385] Next, an electron transport region is placed on top of the light-emitting layer.

[0386] The electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0387] For example, the electron transport region may have a structure of a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.

[0388] The formation conditions of the hole blocking layer, electron transport layer, and electron injection layer of the above electron transport region refer to the formation conditions of the hole injection layer.

[0389] If the above electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

[0390]

[0391] The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the range described above, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

[0392] The electron transport layer may include at least one of the BCP, Bphen, and the following Alq3, BAlq, TAZ, and NTAZ.

[0393]

[0394] Alternatively, the electron transport layer may include at least one of the following compounds ET1 to ET25, but is not limited thereto.

[0395]

[0396]

[0397]

[0398]

[0399] The thickness of the electron transport layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0400] The electron transport layer described above may further include a metal-containing material in addition to the material described above.

[0401] The metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 (lithium quinolate, LiQ) or ET-D2.

[0402]

[0403] Additionally, the electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode (19).

[0404] The electron injection layer may include at least one selected from LiQ, LiF, NaCl, CsF, Li2O, and BaO.

[0405] The thickness of the electron injection layer may be 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 range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0406] A second electrode (19) is provided on the upper portion of the organic layer (15). The second electrode (19) may be a cathode. For the material of the second electrode (19), metals, alloys, electrically conductive compounds having a relatively low work function, and combinations thereof may be used. 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 may be used as materials for forming the second electrode (19). Alternatively, various modifications are possible, such as forming a transparent second electrode (19) using ITO or IZO to obtain a front-emitting element.

[0407] The above organic light-emitting element has been described with reference to FIG. 1, but is not limited thereto.

[0408] According to another aspect, the organic light-emitting element may be included in an electronic device. Accordingly, an electronic device including the organic light-emitting element is provided. The electronic device may include, for example, a display, lighting, a sensor, etc.

[0409] According to another aspect, a diagnostic composition is provided comprising one or more organometallic compounds represented by the above chemical formula 1-1.

[0410] Since the organometallic compound represented by the above chemical formula 1-1 can provide high luminescence efficiency, a diagnostic composition containing the organometallic compound can have high diagnostic efficiency.

[0411] The above diagnostic composition can be applied in various ways to diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc.

[0412] Explanation of terms

[0413] C1-C in this specification 60An alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc. In this specification, C1-C 60 The alkylene group is the C1-C 60 It refers to a divalent group having the same structure as an alkyl group.

[0414] C1-C in this specification 60 The alkoxy group is -OA 101 (Here, A 101 The above C1-C 60 It refers to a monovalent group having the chemical formula of an alkyl group, and specific examples thereof include methoxy groups, ethoxy groups, isopropyloxy groups, etc.

[0415] C2-C in this specification 60 The alkenyl group is the above C2-C 60 It has a structure comprising one or more carbon-carbon double bonds at the middle or terminal of an alkyl group, specific examples thereof including an ethenyl group, a propenyl group, a butenyl group, etc. In this specification, C2-C 60 The alkenylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkenyl group.

[0416] C2-C in this specification 60 The alkynyl group is the above C2-C 60 It has a structure comprising one or more carbon-carbon triple bonds at the middle or terminal of an alkyl group, specific examples thereof including ethynyl groups, propynyl groups, etc. In this specification, C2-C 60 The alkynylene group is the above C2-C 60 It refers to a divalent group having the same structure as an alkynyl group.

[0417] C3-C in this specification 10A cycloalkyl group refers to a monocyclic saturated hydrocarbon group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, etc. In this specification, C3-C 10 The cycloalkylene group is the C3-C 10 It refers to a divalent group having the same structure as a cycloalkyl group.

[0418] C1-C in this specification 10 A heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and specific examples thereof include tetrahydrofuranyl groups, tetrahydrothiophenyl groups, etc. In this specification, C1-C 10 The heterocycloalkylene group is the C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkyl group.

[0419] C3-C in this specification 10 A cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, having at least one carbon-carbon double bond within the ring, but not having aromaticity; specific examples thereof include cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, etc. In this specification, C3-C 10 The cycloalkenylene group is the above C3-C 10 It refers to a divalent group having the same structure as a cycloalkenyl group.

[0420] C1-C in this specification 10 The heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms, comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and having at least one double bond within the ring. The C1-C 10Specific examples of heterocycloalkenyl groups include 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, etc. In this specification, C1-C 10 The heterocycloalkenylene group is the above C1-C 10 It refers to a divalent group having the same structure as a heterocycloalkenyl group.

[0421] C6-C in this specification 60 An aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms, and C6-C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. The above C6-C 60 Specific examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups, chrysenyl groups, etc. The above C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings can be fused together.

[0422] C1-C in this specification 60 A heteroaryl group refers to a monovalent group having a cyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and C1-C 60 A heteroarylene group refers to a divalent group having a carbocyclic aromatic system having 1 to 60 carbon atoms, comprising at least one heteroatom selected from N, O, P, and S as a ring-forming atom. 60 Specific examples of heteroaryl groups include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, isoquinolinyl groups, etc. The above C1-C 60 Heteroaryl group and C1-C 60 If a heteroarylene group contains two or more rings, the two or more rings can be fused together.

[0423] C6-C in this specification 60 The aryloxy group is -OA 102 (Here, A 102 is the above C6-C 60 Pointing to arylgime), and the above C6-C 60 The arylthio group is -SA 103 (Here, A 103 The above C6-C 60 It refers to Arilgiim).

[0424] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed together, and the entire molecule contains only carbon as a ring-forming atom and has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include fluorenyl groups, etc. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0425] In this specification, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed together, and the ring-forming atom includes a heteroatom selected from N, O, P, Si, and S in addition to carbon, and the entire molecule has non-aromaticity. The monovalent non-aromatic heterocondensed heteropolycyclic group includes a carbazole group, etc. In this specification, a divalent non-aromatic heterocondensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic heterocondensed heteropolycyclic group.

[0426] C5-C in this specification 30A carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring-forming atoms. The above C5-C 30 Carbocyclic groups can be monocyclic groups or polycyclic groups.

[0427] C1-C in this specification 30 A heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, and S in addition to 1 to 30 carbons as ring-forming atoms. The above C1-C 30 Heterocyclic groups can be monocyclic groups or polycyclic groups.

[0428] The above-mentioned substituted C5-C 30 Carbocyclic group, substituted C1-C 30 Heterocyclic group, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 Heteroaryl group, substituted C1-C 60 Heteroaryloxy group, substituted C1-C 60 At least one of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituent of the substituted monovalent non-aromatic heterocondensed polycyclic group is,

[0429] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxygenation;

[0430] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic 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 ) and -P(=O)(Q 18 )(Q 19 C1-C substituted with at least one selected from ) 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 Alkoxygenation;

[0431] C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group;

[0432] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic 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 ) and -P(=O)(Q 28 )(Q 29 C3-C substituted with at least one selected from )10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group; and

[0433] -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ) and -P(=O)(Q 38 )(Q 39 );

[0434] Selected from among,

[0435] The above Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0436] For example, Q1 to Q9 in this specification, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently of each other,

[0437] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or

[0438] Deuterium, C1-C 10 Substituted or unsubstituted with an alkyl group, a phenyl group, or any combination thereof, n -Propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -Pentyl, tert -Pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec - It may be an isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group.

[0439] In this specification, "room temperature" refers to a temperature of about 25°C.

[0440] In this specification, "biphenyl group, terphenyl group and tetraphenyl group" each refers to a monovalent group in which two, three, or four phenyl groups are connected to each other through single bonds.

[0441] Hereinafter, compounds and organic light-emitting devices according to one embodiment of the present invention will be described in more detail with reference to synthesis examples and embodiments, but the present invention is not limited to the following synthesis examples and embodiments. In the following synthesis examples, the amount of 'B' used instead of 'A' in the expression "'B' was used instead of 'A'" is the same as the amount of 'A' used in terms of molar equivalents.

[0442] [Example]

[0443] Synthesis Example 1: Synthesis of Compound Pt-4

[0444]

[0445]

[0446] (1) Synthesis of intermediate Pt-4-IM2

[0447] 2-(3-(1H-benzo[d]imidazol-1-yl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-6-chloro-9H-carbazole (10.86 g, 20 mmol), 3,11-di-tert-butyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene (15.25 g, 30 mmol), palladium (II) acetate (0.90 g, 4 mmol), SPhos (3.28 g, 8 mmol) and potassium phosphate tribasic (8.49 g, 40 mmol) were mixed with 1,4-Dioxane / H2O (4: 1, 200 ml), The mixture was stirred at 100 ℃ for 16 hours. After the reaction was complete, the mixture was cooled to room temperature. The organic layer extracted using saturated ammonium chloride (NH4Cl) and methylene chloride (MC) was dried and filtered with anhydrous magnesium sulfate (MgSO4), and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain the intermediate Pt-4-IM2 (8.89 g, 10.0 mmol, yield = 50%).

[0448] LC-Mass (Calculated value: 888.42 g / mol, Measured value M+1 = 889 g / mol)

[0449] (2) Synthesis of intermediate Pt-4-IM1

[0450] Intermediate Pt-4-IM2 (8.89 g, 10.0 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (7.56 g, 13.0 mmol), and copper (II) acetate (0.36 g, 2.0 mmol) were mixed with 40 ml of DMF and stirred at 100 °C for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA) was dried and filtered with anhydrous magnesium sulfate (MgSO4), and then concentrated under reduced pressure. Silica gel column chromatography was performed on the product obtained therefrom to obtain the intermediate Pt-4-IM1 (10.31 g, 8.40 mmol, yield = 84%).

[0451] LC-Mass (Calculated value: 1077.56 g / mol, Measured value M+ = 1077 g / mol)

[0452] (3) Synthesis of compound Pt-4

[0453] Intermediate Pt-4-IM1 (10.31 g, 8.40 mmol), Pt(COD)Cl2 (3.46 g, 9.24 mmol), and sodium acetate (2.07 g, 25.20 mmol) were mixed with 420 ml of benzonitrile and stirred at 180°C for 18 hours. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain compound Pt-4 (3.31 g, 2.60 mmol, yield = 31%).

[0454] LC-Mass (Calculated value: 1269.53 g / mol, Measured value M+1 = 1270 g / mol)

[0455] Synthesis Example 2: Synthesis of Compound Pt-6

[0456]

[0457]

[0458] (1) Synthesis of intermediate Pt-6-IM2

[0459] 2-(3-(tert-butyl)-5-(1H-imidazol-1-yl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-6-chloro-9H-carbazole (10.98 g, 20 mmol), 3,11-di-tert-butyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene (15.25 g, 30 mmol), palladium (II) acetate (0.90 g, 4 mmol), s-phos (3.28 g, 8 mmol) and potassium phosphate tribasic (8.49 g, 40 mmol) with 1,4-Dioxane / H2O (4:1, 200 ml) After mixing, the mixture was stirred at 100°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (NH4Cl) and methylene chloride (MC) was dried and filtered with anhydrous magnesium sulfate (MgSO4), followed by concentration under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain the intermediate Pt-6-IM2 (10.01 g, 11.2 mmol, yield = 56%).

[0460] LC-Mass (Calculated value: 894.47 g / mol, Measured value M+1 = 895 g / mol)

[0461] (2) Synthesis of intermediate Pt-6-IM1

[0462] Intermediate Pt-6-IM2 (10.01 g, 11.2 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (8.51 g, 14.56 mmol), and copper (II) acetate (0.41 g, 2.24 mmol) were mixed with 45 ml of DMF and stirred at 100°C for 1 hour. After the reaction was finished, the mixture was cooled to room temperature, and the organic layer extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA) was dried and filtered with anhydrous magnesium sulfate (MgSO4), and then concentrated under reduced pressure. Silica gel column chromatography was performed on the product obtained therefrom to obtain the intermediate Pt-6-IM1 (10.44 g, 9.63 mmol, yield = 86%).

[0463] LC-Mass (Calculated value: 1083.63 g / mol, Measured value M+ = 1083 g / mol)

[0464] (3) Synthesis of compound Pt-6

[0465] Intermediate Pt-6-IM1 (10.44 g, 9.63 mmol), Pt(COD)Cl2 (3.96 g, 10.59 mmol), and sodium acetate (2.37 g, 28.89 mmol) were mixed with 480 ml of benzonitrile and stirred at 180°C for 18 hours. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain compound Pt-6 (4.79 g, 3.76 mmol, yield = 39%).

[0466] LC-Mass (Calculated value: 1275.57 g / mol, Measured value M+1 = 1276 g / mol)

[0467] Synthesis Example 3: Synthesis of Compound Pt-26

[0468]

[0469]

[0470] (1) Synthesis of intermediate Pt-26-IM2

[0471] 2-(3-(1H-benzo[d]imidazol-1-yl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-6-chloro-9H-carbazole (10.86 g, 20 mmol), 2,5-di-tert-butyl-11-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (14.38 g, 30 mmol), palladium (II) acetate (0.90 g, 4 mmol), s-phos (3.28 g, 8 mmol), and potassium phosphate tribasic (8.49 g, 40 mmol) were mixed with 1,4-Dioxane / H2O (4:1, 200 ml) and stirred at 100°C for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (NH4Cl) and methylene chloride (MC) was dried and filtered with anhydrous magnesium sulfate (MgSO4), and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain the intermediate Pt-26-IM2 (9.63 g, 11.2 mmol, yield = 56%).

[0472] LC-Mass (Calculated value: 859.43 g / mol, Measured value M+1 = 860 g / mol)

[0473] (2) Synthesis of intermediate Pt-26-IM1

[0474] Intermediate Pt-26-IM2 (9.63 g, 11.2 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (8.50 g, 14.56 mmol), and copper (II) acetate (0.41 g, 2.24 mmol) were mixed with 45 ml of DMF and stirred at 100°C for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA) was dried and filtered with anhydrous magnesium sulfate (MgSO4), and then concentrated under reduced pressure. Silica gel column chromatography was performed on the product obtained therefrom to obtain the intermediate Pt-26-IM1 (11.41 g, 9.52 mmol, yield = 85%).

[0475] LC-Mass (Calculated value: 1048.59 g / mol, Measured value M+ = 1048 g / mol)

[0476] (3) Synthesis of compound Pt-26

[0477] Intermediate Pt-26-IM1 (11.41 g, 9.52 mmol), Pt(COD)Cl2 (3.92 g, 10.47 mmol), and sodium acetate (2.34 g, 28.56 mmol) were mixed with 476 ml of benzonitrile and stirred at 180°C for 18 hours. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain compound Pt-26 (3.55 g, 2.86 mmol, yield = 30%).

[0478] LC-Mass (Calculated value: 1240.53 g / mol, Measured value M+1 = 1241 g / mol)

[0479] Synthesis Example 4: Synthesis of Compound Pt-47

[0480]

[0481] (1) Synthesis of intermediate Pt-47-IM1

[0482] 9-(4-(tert-butyl)pyridin-2-yl)-6-chloro-2-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy)-9H-carbazole (10.42 g, 20 mmol), 2,5-di-tert-butyl-11-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (14.38 g, 30 mmol), palladium (II) acetate (0.90 g, 4 mmol), s-phos (3.28 g, 8 mmol), and potassium phosphate tribasic (8.49 g, 40 mmol) were mixed with 1,4-Dioxane / H2O (4:1, 200 ml) and stirred at 100°C for 16 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer extracted using saturated ammonium chloride (NH4Cl) and methylene chloride (MC) was dried and filtered with anhydrous magnesium sulfate (MgSO4), and then concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain the intermediate Pt-47-IM1 (10.06 g, 11.6 mmol, yield = 58%).

[0483] LC-Mass (Calculated value: 866.44 g / mol, Measured value M+1 = 865 g / mol)

[0484] (2) Synthesis of Compound Pt-47

[0485] Intermediate Pt-47-IM1 (10.06 g, 11.6 mmol) and PtCl2(PhCN)2 (5.48 g, 11.6 mmol) were mixed with 580 ml of benzonitrile and stirred at 180°C for 18 hours. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure. Silica gel column chromatography was performed on the resulting product to obtain compound Pt-47 (4.92 g, 4.64 mmol, yield = 40%).

[0486] LC-Mass (Calculated value: 1059.39 g / mol, Measured value M+1 = 1060 g / mol)

[0487] Evaluation Example 1: PL Spectrum Evaluation

[0488] Compounds Pt-4, Pt-26, and Comparative Compound C1, each in 10 toluene -4 After diluting to a concentration of M, the photoluminescence (PL) spectrum was measured at room temperature using an ISC PC1 spectrofluorometer equipped with a xenon lamp and is shown in Fig. 2. From the PL spectrum of each compound, the maximum emission wavelength, full width at half maximum (FWHM), intensity of the second peak, and CIE y-coordinate values ​​were calculated and are shown in Table 2 below.

[0489] Maximum emission wavelength (nm) Half width (nm) Second peak intensity CIE y-coordinate C1 460 20 0.419 0.140 Pt-4 461 21 0.383 0.137 Pt-26 461 21 0.365 0.129

[0490] From Table 2 above, compounds Pt-4 and Pt-26 according to one embodiment show a reduced intensity of the second emission peak and smaller CIE y-coordinate values ​​compared to comparative compound C1. From this, it can be confirmed that the compounds according to one embodiment emit deep blue light compared to the comparative compounds.

[0491] Example 1

[0492] A glass substrate having an ITO (Indium tin oxide) electrode (first electrode, anode) with a thickness of 500 Å formed thereon was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, ultrasonic cleaning was performed using isopropyl alcohol, acetone, and methanol in sequence, and after drying, the substrate was transferred to a plasma cleaner, and then cleaned with oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine.

[0493] A first hole injection layer of 3500 Å was formed by vacuum depositing compound HT3 on the ITO electrode of the glass substrate, a second hole injection layer of 300 Å was formed by vacuum depositing compound HT-D1 on the first hole injection layer, and an electron blocking layer of 100 Å was formed by vacuum depositing TAPC on the second hole injection layer to form a hole transport region.

[0494] Compound H52 and compound Pt-4 (10 wt%) were co-deposited on the above hole transport region to form a 300 Å thick emissive layer.

[0495] An organic light-emitting device was fabricated by vacuum depositing compound ET3 on the light-emitting layer to form an electron transport layer with a thickness of 250 Å, then depositing ET-D1 (Liq) on the electron transport layer to form an electron injection layer with a thickness of 5 Å, and forming an Al second electrode (cathode) with a thickness of 1000 Å on the electron injection layer.

[0496]

[0497] Example 2

[0498] An organic light-emitting device was fabricated using the same method as in Example 1, except that compound Pt-26 was used instead of compound Pt-4 when forming the light-emitting layer.

[0499] Comparative Example 1

[0500] An organic light-emitting device was fabricated using the same method as in Example 1, except that compound C1 was used instead of compound Pt-4 when forming the light-emitting layer.

[0501] Evaluation Example 2: Characterization of Organic Light Emitting Diodes

[0502] For each organic light-emitting diode fabricated in Examples 1 and 2 and Comparative Example 1, the maximum emission wavelength of the EL spectrum, driving voltage, and external quantum emission efficiency were evaluated, and the results are shown in Table 3. The maximum emission wavelength of the EL spectrum was determined for each organic light-emitting diode using a luminance meter (Minolta Cs-1000A) at 1000 cd / m² 2 The driving voltage and external quantum luminescence efficiency were evaluated using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A).

[0503] Dopant Compound No. Maximum emission wavelength (nm) Driving voltage (V), relative value (%) External quantum luminescence efficiency EQE (1000 cd / m²) 2 Relative value (%) Example 1 Pt-4 463 97 107 Example 2 Pt-26 463 96 109 Comparative Example 1 C1 462 100 100

[0504] <Compound C1>

[0505]

[0506] From Table 3 above, it can be seen that the organic light-emitting devices of Examples 1 and 2 exhibit lower driving voltage and higher external quantum emission efficiency compared to the organic light-emitting device of Comparative Example 1. Explanation of the symbols

[0507] 10: Organic light-emitting diode 11: First electrode 15: Organic layer 19: Second electrode

Claims

Claim 1 Organometallic compound represented by any one of the following chemical formulas 1-1A to 1-1E: <Chemical Formula 1-1A> <Chemical Formula 1-1B> <Chemical Formula 1-1C> <Chemical Formula 1-1D> <Chemical Formula 1-1E> In the above chemical formulas 1-1A and 1-1B, X1 is C, and X2 to X4 are independently C or N; in the above chemical formulas 1-1C to 1-1E, X1 to X4 are independently C or N; in the above chemical formulas 1-A to 1-E, M1 is Pt, and T2 is *-O-*', *-S-*', *-Se-*', *-C(R 50 )(R 60 )-*', *-B(R 50 )-*' or *-N(R 50 )-*' and, Z 11 To Z 15 are independent of each other, R 10 Igo, Z 21 To Z 23 are independent of each other, R 20 Igo, Z 31 To Z 36 are independent of each other, R 30 or E1 and Z 41 To Z 44 are independent of each other, R 40 And, among the above chemical formulas 1-1A to 1-1E, Z 31 To Z 36 At least one of them is E1, and E1 is a group represented by any one of the following chemical formulas 2-2 to 2-4, and Among the above chemical formulas 2-2 to 2-4, Y 21 is B, P, P(=O) or N, and K1 to K3 are independently single bonds, B(R 204 ), N(R 205 ), O, S, Se, C(=O) or S(=O)2 and,R 10 , R 20 , R 30 , R 40 , R 50 , R 60 and R 201 to R 205 are independently hydrogen, deuterium, -F, cyano groups, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C1-C 60 A heteroaryloxy group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2) or -B(Q6)(Q7), wherein R 202 and R 203 Each is not hydrogen, c201 to c203 are independently one of integers from 1 to 10, and the substituted C1-C 60 Alkyl groups, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C6-C 60 aryl group, substituted C1-C 60 Heteroaryl group, substituted C1-C 60 The substituents of the heteroaryloxy group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group are deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, or phosphate group or a salt thereof; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphate group or thereof Salt, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic 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 ) or substituted or unsubstituted by any combination thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group or C1-C 60 Alkoxy group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, C1-C 60 Alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ) or substituted or unsubstituted with any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic 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 ) or -P(=O)(Q 38 )(Q 39 ); or any combination thereof; and, above Q1 to Q9, Q 11 to Q 19 , Q 21 to Q 29 and Q 31 to Q 39 are independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amido group; hydrazine group; hydrazone group; carboxylic acid group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 Alkyl group, C6-C 60 C1-C substituted or unsubstituted with an aryl group, or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl group, C6-C 60 C6-C6 substituted or unsubstituted with an aryl group, or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 delete Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 delete Claim 10 In claim 1, among the above chemical formulas 2-2 to 2-4, i) Y 21 ☐ is B, and K1 to K3 are each O or; ii) Y 21 is B, and K1 to K3 are each N(R 205 ) or;iii) Y 21 is B, at least one of K1 to K3 is O, and at least one of K1 to K3 is N(R 205 ) or;iv) Y 21 is N, and K1 to K3 are each single bonds or;v) Y 21 is N, and K1 to K3 are each C(=O) or, vi) Y 21 An organometallic compound in which N is and K1 to K3 are each S(=O)2. Claim 11 delete Claim 12 delete Claim 13 delete Claim 14 In claim 1, Z among the above chemical formulas 1-1A and 1-1E 11 To Z 15 are identical or different from each other, and Z among the above chemical formulas 1-1B to 1-1D 11 To Z 13 are identical or different from each other, and among the above chemical formulas 1-1A to 1-1E, Z 21 To Z 23 are identical or different from each other, and Z 31 To Z 33 , Z 35 and Z 36 are respectively R 30 Igo, Z 31 To Z 33 , Z 35 and Z 36 are identical or different from each other, and Z 34 is E1 and Z 41 To Z 44 are respectively R 40 Igo, Z 41 To Z 44 Organometallic compounds that are identical or different from each other. Claim 15 An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer comprises one or more organometallic compounds of any one of claims 1, 10 and 14. Claim 16 An organic light-emitting device according to claim 15, wherein one or more of the above-mentioned organometallic compounds are included in the light-emitting layer. Claim 17 An organic light-emitting device according to claim 16, wherein the light-emitting layer comprises a host and a dopant, and the dopant comprises one or more organometallic compounds. Claim 18 In claim 16, the above-mentioned light-emitting layer is an organic light-emitting device that emits blue light. Claim 19 An organic light-emitting device according to claim 15, wherein the first electrode is an anode and the second electrode is a cathode, and the organic layer further comprises 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, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. Claim 20 An electronic device comprising the organic light-emitting element of paragraph 15.

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