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

Abstract

A novel organometallic compound, an organic light-emitting device employing the same, and an electronic device including the organic light-emitting device are provided. [Solution] The organometallic compound according to the present invention has a C2 symmetric structure and is represented by (chemical formula 1) Ir(L1)2(L2), and is characterized in that the sum of Δ(Ir-N) and Δ(Ir-C) is 0.002 Å or less.

Description

[Technical Field]

[0001] The present invention relates to an organometallic compound, an organic light-emitting device containing the same, and an electronic device containing the organic light-emitting device. The device has, in particular, excellent outcoupling efficiency, short decay time, and improved horizontal Organometallic compound having orientation coefficient, organic light-emitting device containing the same, and device containing organic light-emitting device Regarding child devices. [Background technology]

[0002] Organic light emitting devices are It is a self-luminous element with excellent viewing angle, response time, brightness, driving voltage and response speed characteristics. Multicolorization is possible. According to one example, the organic light emitting device comprises an anode, a cathode, and a layer between the anode and the cathode. and an organic layer including a light-emitting layer. Between the anode and the light-emitting layer, a hole transport region is provided, and between the light-emitting layer and the cathode, , an electron transport region is provided. Holes injected from the anode travel through the hole transport region to the light-emitting layer and are released from the cathode. The electrons injected from the electron transport region are transported to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to form excitons. Light is generated as the exciton changes from the excited state to the ground state.

[0003] The quality of organometallic compounds used in organic layers, including the light-emitting layer of organic light-emitting devices, is constantly being checked. With the goal of improving the quality and performance of these materials, the development of new organometallic compounds is becoming a challenge. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2016-69379 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention has been made in view of the above-mentioned problems with conventional organometallic compounds, and The present invention aims to provide a novel organometallic compound, an organic light-emitting device using the compound, and an organic light-emitting device including the compound. The present invention aims to provide an electronic device that [Means for solving the problem]

[0006] In order to achieve the above object, the organometallic compound according to the present invention has a C2 symmetric structure. death, It is represented by the following chemical formula 1: The sum of Δ(Ir-N) and Δ(Ir-C) is 0.002 Å or less. machine metal compound. (chemical 1) Ir(L1)2(L2)...Chemical formula 1 (In the above Chemical Formula 1, L1 is a ligand represented by the following chemical formula 2: L2 is a ligand represented by the following chemical formula 3: One of the two L1s is a first L1 ligand and the remaining one is a second L1 ligand. the law of nature, the first L1 ligand and the second L1 ligand are identical to each other; [ka] [ka] In the above formula 2, Y1 is N and Y2 is C; In Formula 2, ring CY1 is a polycyclic group in which three or more 6-membered rings are fused to each other; In the formula 2, the ring CY2 is C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic group the law of nature, In the formula 2, T1 is a para Hammett substituent constant (para H ammett substituent constant)(σ p ) is a group having a value the law of nature, In the above formula 2, b1 is an integer of 1 to 10, and when b1 is 2 or more, T1 may be identical to or different from each other, In the formulas 2 and 3, R1, R2, and R 31 ~R 33 are, independently of each other, hydrogen, Deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group , an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, sulfur a phosphonic acid group or its salt, a phosphate group or its salt, a substituted or unsubstituted C1-C 60 Alkyl Group, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C6 0 alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloar alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl group , substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or represents an unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4) (Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)( Q9) and In the formula 2, a1 and a2 are each independently an integer of 0 to 10, and a1 is 2. or more, two or more R1 are the same or different, and a2 is When R2 is 2 or more, the 2 or more R2's are the same or different from each other, In Chemical Formulas 2 and 3, * and *' are the bonding sites with Ir in Chemical Formula 1, respectively. the law of nature, The Δ(Ir-N) is the bond between Ir and the first L1 ligand Y1 in Chemical Formulas 1 and 2. the absolute value of the difference between the distance between Ir and Y1 of the second L1 ligand and the distance between Ir and Y1 of the second L1 ligand, The Δ(Ir-C) is the bond between Ir and the first L1 ligand Y2 in Chemical Formulas 1 and 2. the absolute value of the difference between the distance between Ir and Y2 of the second L1 ligand, and the distance between Ir and Y2 of the second L1 ligand, Two or more of the a1 R1 may optionally be bonded to each other, and at least one R 1a Place Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Replace with or Unsubstituted C1-C 30 can form a heterocyclic group, Two or more of the a2 R2 may optionally be bonded to each other, and at least one R 1a in Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1aReplace with or is unsubstituted C1-C 30 can form a heterocyclic group, In R1 and R2, two or more may be optionally bonded to each other, and at least one R 1a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Replace with or unsubstituted C1-C 30 can form a heterocyclic group, R 31 ~R 33 In the formula, two or more are optionally bonded to each other, and at least one R1 a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Replace with or unsubstituted C1-C 30 can form a heterocyclic group, R 1a For the explanation of R1, refer to the explanation of R1 above. The substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C 3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl Groups, substituted C6-C 60 Aryl groups, substituted C6-C 60 Aryloxy group, Replaced C6-C 60 Arylthio groups, substituted C1-C 60 Heteroaryl groups, substituted Substituents of substituted monovalent non-aromatic fused polycyclic groups and substituted monovalent non-aromatic fused heteropolycyclic groups are independent of each other, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkini C1-C 60 alkoxy groups, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3 -C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 a Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17), -P(=O)(Q 18 )(Q 19 ), -P( Q 18 )(Q 19 ), or any combination thereof, C1-C 60 Alkyl group, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, or C1-C 60 Alcoki Si group, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkini group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Hetero Cycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkane Nyl group, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Ally Ruthio group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic heteroaryl groups Condensed 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)(Q2 8)(Q 29 ), -P(Q 28 )(Q 29 ), or any combination thereof. Unsubstituted, C3-C 10 Cycloalkyl groups, C1-C 10 heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C6 0 aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ), or any combination thereof; The above Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q 39 are mutually exclusive In other words, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitrite group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, deuterium, C1-C 60 Alkyl groups, C6-C 60 a aryl groups, or any combination thereof, substituted or unsubstituted C1-C 60 Archi group, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C1 0 cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, deuterium, C1-C 60 Alkyl groups, C6-C 60 aryl groups, or any combination thereof, substituted or Unsubstituted C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Ally Ruthio group, C1-C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic It is a hetero-fused polycyclic group.

[0007] In order to achieve the above object, the present invention provides an organic light-emitting device comprising a first electrode and a second electrode. an organic layer disposed between the first electrode and the second electrode and including an emitting layer; The organic layer is characterized by containing one or more organometallic compounds of the present invention.

[0008] In the organic layer, the organometallic compound contained in the light-emitting layer acts as a dopant. It is possible.

[0009] The electronic device according to the present invention, which has been made to achieve the above object, comprises the organic light-emitting element of the present invention. It is characterized by including. [Effects of the Invention]

[0010] The organometallic compound according to the present invention, an organic light-emitting device containing the same, and an electrode containing the organic light-emitting device According to the device, organometallic compounds have excellent outcoupling efficiency, short decay times, and Organic light-emitting device employing organometallic compound and having improved horizontal alignment rate, and organic light-emitting device An electronic device including the element can advantageously have high luminous efficiency. [Brief explanation of the drawings]

[0011] [Figure 1] 1 is a perspective view showing a simplified view of an organometallic compound represented by Chemical Formula 1 laminated on the surface of a predetermined film A according to an embodiment of the present invention. [Figure 2] FIG. 2 is a simplified diagram showing the relationship between the C2 symmetry axis, transition dipole moment (TDM), horizontal alignment ratio of the transition dipole moment (TDM) (TDMH), and vertical alignment ratio of the transition dipole moment (TDM) (TDMV) of an organometallic compound represented by chemical formula 1 with respect to a given film A surface. [Figure 3] 1 is a cross-sectional view showing a schematic configuration of an organic light-emitting device according to one embodiment of the present invention. [Figure 4] FIG. 1 is a diagram illustrating a group linked to Ir via N and a group linked to Ir via C in Compound 1. DETAILED DESCRIPTION OF THE INVENTION

[0012] Next, the organometallic compound according to the present invention, the organic light-emitting element containing the same, and the organic light-emitting element A specific example of an embodiment of an electronic device including the same will be described with reference to the drawings.

[0013] The organometallic compound of the present invention is represented by the following chemical formula 1: is expressed as follows. (chemical 1) Ir(L1)2(L2)...Chemical formula 1

[0014] The organometallic compound represented by chemical formula 1 contains one iridium (Ir) and has the chemical formula 1 L1 is a ligand represented by the following chemical formula 2, and L2 is a ligand represented by the following chemical formula 3. It is a ligand represented by the formula: [ka] [ka]

[0015] In Formula 2, Y1 is N and Y2 is C. For detailed descriptions relating to Formulas 2 and 3, please refer to the descriptions herein. One of the two L1 in Formula 1 is a first L1 ligand. The remaining one is a second L1 ligand nd). The first L1 ligand and the second L1 ligand can be identical to each other. In Formula 1, two L1s (i.e., the first L1 ligand and the second L1 ligand) are mutually Since L2 is a ligand represented by chemical formula 3, it is Organometallic compounds have a C2 symmetry axis. It may have a structure.

[0016] The sum of Δ(Ir-N) and Δ(Ir-C) of the organometallic compound represented by chemical formula 1 is 0. 0.002Å or less, 0Å to 0.002Å, 0Å to 0.001Å, 0Å to 0.0009Å, 0Å It can be 0.0008 Å or 0 Å to 0.00072 Å. Here, Δ(Ir-N) is the bond between Ir and the first L1 ligand Y1 in Formulas 1 and 2. the absolute value of the difference between the distance (e.g., bond distance) and the distance between Ir and Y1 of the second L1 ligand is the absolute value of the difference between D1(Ir-N) and D2(Ir-N) in chemical formula 1a, and Δ (Ir-C) is the distance between Ir and Y2 of the first L1 ligand in chemical formulas 1 and 2, and the distance between Ir and Y2 of the first L1 ligand in chemical formula 2. and the absolute value of the difference between the distance to Y2 of the second L1 ligand, and in the chemical formula 1a shown below, It is the absolute value of the difference between D1(Ir-C) and D2(Ir-C). [ka]

[0017] The sum of Δ(Ir-N) and Δ(Ir-C) of the organometallic compound represented by chemical formula 1 is By satisfying the above range, the vibrational state of the S0 level of the organometallic compound (vibr onic state) has symmetrical properties, and the organometallic compound represented by chemical formula 1 Reduced T1-S0 transition in the excited state of the compound It can be done. As a result, the PL (photoluminescence) spectrum of the organometallic compound and / or EL (electroluminescence) spectrum half width (FW HM) and / or FWQM (full width at quarter maximum um) is reduced, and an electronic device employing the organometallic compound represented by Chemical Formula 1, for example, The organic light emitting device can have excellent color purity and high luminous efficiency.

[0018] According to another embodiment, L of the organometallic compound represented by formula 1 N / L C is 1.45 ~2.88, 1.45~2.50, 1.46~2.30, 1.47~2.20, 1.48 It can be 1.491 to 2.128. where L N is the chemical formula 2 The maximum distance between the non-hydrogen atom contained in the group represented by TIFF2026042033000007.tif45145 and Ir in chemical formula 1. the law of nature, L C is the chemical formula 2 The maximum distance between the non-hydrogen atom contained in the group represented by TIFF2026042033000008.tif38145 and Ir in chemical formula 1. (See Figure 1.)

[0019] As mentioned above, L N , L C , Δ(Ir-N), and Δ(Ir-C) are the organic gold of formula 1. It can also be measured by performing DFT (density functional theory) calculations on the compound. For example, the DFT calculations can be performed using Gaussians. According to one embodiment, during DFT calculation, the molecular structure optimization of the organometallic compound of Formula 1 is For iridium, the B3LYP / LanL2DZ function is used, and the ligands (L1 and For L2), the B3LYP / 6-31G(G,P) function can be used.

[0020] When the organometallic compound represented by Chemical Formula 1 is laminated on top of Film A (Layer A), 1) Two ligands L1 represented by chemical formula 2 are aligned along the surface (xy plane) of membrane A. And, 2) One ligand L2 represented by chemical formula 3 is oriented in the opposite direction ( i.e., aligned on the vacuum side in the z-axis direction. Here, the C2 symmetry axis of Chemical Formula 1 and the bonding direction between Ir and the ligand L2 are parallel to each other. The transition dipole moment (TDM) of the organometallic compound represented by chemical formula 1 is The dipole moment is perpendicular to the C2 axis of symmetry (see Figure 2). ).

[0021] L of the organometallic compound represented by chemical formula 1 N / L C The above-mentioned range is satisfied. As a result, the angle (θ) between the C2 symmetry axis of Chemical Formula 1 and the surface of Film A becomes smaller. The transition dipole moment (T DM) is i) Horizontal orientation of transition dipole moment (TDM) ntation ratio), i.e., TDM H and, ii) Vertical orientation of transition dipole moment (TDM) tation ratio), i.e., TDM V This can be shown by adding ( See Figure 2). The smaller the angle (θ) between the C2 symmetry axis of chemical formula 1 and the surface of membrane A, the greater the TDM H The transition dipole moment (TDM) of the organometallic compound is increased relative to the surface of the membrane A. It becomes qualitatively level. For example, the transition dipole moment (TDM) of the organometallic compound and the angle between the surface of film A can be between 0° and 10°.

[0022] Thus, the transition dipole moment (TDM) of the organometallic compound represented by formula 1 is , when it is substantially horizontal to the surface of the film A, an electronic device containing an organometallic compound, e.g. When the organic light-emitting device is driven, an electric field is emitted in a direction substantially parallel to the surface of the film A. , waveguide mode and / or surface plasmon polariton mode Light loss due to surface plasmon polariton mode can be reduced. Therefore, the aforementioned L N / L C An organometallic compound represented by chemical formula 1 that satisfies the range The electronic device employed, for example, an organic light-emitting device, has a high outcoupling efficiency (out-coupling efficiency). and electrons with high luminous efficiency. A device (e.g., an organic light emitting device) can be realized.

[0023] On the other hand, the maximum external quantum efficiency (maximum external quantum efficiency) of an organic light-emitting device The net efficiency is calculated using the following formula 1: (Number 1) η maxEQE =γΦη S / T η out Formula 1 In Equation 1, η maxEQE is the maximum external quantum efficiency, γ is the charge balance, Φ is the quantum efficiency, η S / T is the singlet / triplet fraction ) and η out is the outcoupling efficiency.

[0024] On the other hand, the external quantum efficiency (EXQE) of an organic light-emitting device at a target luminance is The efficiency at target luminance is It is calculated as shown in Equation 2 below. (Number 2) η EQE =η maxEQE (1-r) Equation 2 In Equation 2, η EQE is the external quantum efficiency at the target luminance, r is the roll-off ratio.

[0025] That is, from Equation 1 and Equation 2, in order to improve the luminous efficiency of the organic light emitting device, The external quantum efficiency must be increased and the roll-off ratio must be reduced, but the maximum external quantum efficiency must be increased. To increase the efficiency, it is necessary to increase the outcoupling efficiency. The organometallic compound has an L N / L C When the compound has a molecular structure that satisfies the above, Organic light-emitting diodes employing organometallic compounds that can provide high outcoupling efficiency The device can have an improved maximum external quantum efficiency, resulting in high luminous efficiency. An organic light emitting device can be realized.

[0026] In Chemical Formula 2, ring CY1 may be a polycyclic group in which three or more 6-membered rings are fused together. For example, the six-membered ring is a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, It may be a pyrimidine group, a pyrazine group, or a pyridazine group. According to one embodiment, in Formula 2, ring CY1 is a ring in which three or four six-membered rings are fused together. The group may be a polycyclic group. In formula 2, ring CY2 is C5-C 30 Carbocyclic group or C1-C 30 It may be a heterocyclic group. do.

[0027] For example, in formula 2, ring CY2 is i) ring 1, ii) second ring; iii) a fused ring in which two or more first rings are fused to each other; iv) a fused ring in which two or more second rings are fused together; or v) one or more first rings and one or more second rings are fused to each other; The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrolidone group, or a cyclopentadiene group. hydroxyl group, silole group, germole group, borole group, selenophene group, phosphole group, oxy group thiazolyl group, oxadiazole group, oxatriazole group, thiazole group, thiadiazolyl group triazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group azasilole group, azagermol group, azaborole group, azaselenophene group, or is an azaphosphole group, The second ring may be an adamantane group, a norbornane group (bicyclo[2.2.1]heptane group), Norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group, cyclohexane group, cyclohexene group, benzene group a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group; obtain.

[0028] According to one embodiment, in Formula 2, the ring CY2 is a cyclopentane group, a cyclohexane group, , a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, Triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group , thiophene group, furan group, pyrrole group, cyclopentadiene group, silole group, borole group, phosphole group, selenophene group, germole group, benzothiophene group, benzofuran group group, indole group, indene group, benzosilole group, benzoborole group, benzophospho benzoyl group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, Lanthanide group, carbazole group, fluorene group, dibenzosilole group, dibenzoborole group, dibenzosilole group, Benzophosphole group, dibenzoselenophene group, dibenzogermole group, dibenzothiophene phenyl 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group oxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaine Azabenzosilole group, azabenzoborole group, azabenzophosphole group, aza benzoselenophene group, azabenzogermole group, azadibenzothiophene group, azadibenzyl azafuran group, azacarbazole group, azafluorene group, azadibenzosilole group, aza Dibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadi Benzogermol group, azadibenzothiophene 5-oxide group, aza-9H-fluorene -9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxa Phosphorus group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazo oxazole group, isoxazole group, thiazole group, isothiazole group, oxazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazo quinol group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydro It may be a quinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0029] According to another embodiment, in Formula 2, the ring CY2 is a benzene group, a naphthalene group, a 1,2 ,3,4-tetrahydronaphthalene group, thiophene group, furan group, pyrrole group, cyclopentadiene group diphenylene group, silole group, benzothiophene group, benzofuran group, indole group, indole group, benzosilole group, dibenzothiophene group, dibenzofuran group, carbazole group , a fluorene group, or a dibenzosilole group.

[0030] In chemical formula 2, T1 is greater than "0" and less than "0.5" (e.g., 0.01 to 0.4 or 0. Para Hammett substituent constants (0.1-0.3) uent constant)(σ p ) values. Para-Hammett substituent constant (σ) greater than "0" and less than "0.5" p ) specific group having a value Examples include, for example, "Hansch et al., A Survey of Hamme tt substituent Constants and Resonance a nd Field Parameters, Chem. Rev. 1991, 91 , 165-195.

[0031] According to one embodiment, in Formula 2: T1 is a fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl groups, C3-C 10 Cycloalkane group, C1-C 10 heterocycloalkyl group, phenyl group, biphenyl group, or any of these groups Fluorinated C1-C, substituted or unsubstituted in any combination 20 Alkyl groups, fluorinated C3 -C 10 Cycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, fluorinated phenyl groups C1-C containing phenyl, fluorinated biphenyl, and cyano groups 20Alkyl group, cyano group-containing C3- C 10 Cycloalkyl groups, cyano-containing C1-C 10 Heterocycloalkyl group, cyano group The phenyl group may be a phenyl group containing a cyano group, or a biphenyl group containing a cyano group.

[0032] In Chemical Formula 2, b1 represents the number of T1 and is an integer of 1 to 10. That is, the ring CY1 of Chemical Formula 2 is necessarily substituted with at least one T1. When b1 is 2 or more, the two or more T1 may be the same or different. stomach. For example, b1 can be 1, 2, or 3. As mentioned above, the ring CY1 in formula 2 must be substituted with at least one T1. Therefore, the charge transfer in the ligand L1 represented by chemical formula 2 r) occurs rapidly, and the organometallic compound of formula 1 has a relatively short decay time. It is possible.

[0033] Increasing the brightness of an organic light-emitting device requires the use of excitons and polarons (pol This results in a high density of excitons, which facilitates energy transfer between excitons and / or As energy transfer between excitons and polarons occurs, quenching occurs, resulting in As a result, roll-off may occur. Here, a polaron means a particle that carries an electric charge. In order to reduce the quenching phenomenon, the exciton density in the light-emitting layer must be reduced or the exciton density must be increased. This shortens the time that excitons remain in the emitting layer, and reduces the diffusion length of excitons in the emitting layer. length) needs to be shortened. Here, the time during which the organometallic compound exists as an exciton is the time during which the organometallic compound remains in the triplet state. The decay time is the time during which the organometallic compound decays. This reduces the roll-off ratio of organic light-emitting devices that employ organometallic compounds, resulting in high An organic light emitting device having high luminous efficiency can be realized. The decay time is the TRPL (time It is also evaluated from the (resolved photoluminescence) spectrum. can be.

[0034] In Formulas 2 and 3, R1, R2, and R 31 ~R 33 are hydrogen, heavy water, and -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfone Acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 alkyl groups, Substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 a Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C 3-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 groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted Substituted monovalent non-aromatic condensed polycyclic radicals lycyclic group), substituted or unsubstituted monovalent non-aromatic fused heterocyclic polycyclic group (non-aromatic condensed heteropolycyclic group), -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q 3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or - It could be P(Q8)(Q9). For explanations of Q1 to Q9, please refer to the respective descriptions in this specification.

[0035] For example, each of R1 and R2 is not hydrogen. For example, in Formulas 2 and 3, R1, R2, and R 31 ~R 33 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfo Phosphate group or its salt, Phosphate group or its salt, -SF5, C1-C 20 Alkyl group or C1 -C 20 alkoxy groups, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Phosphate group or its salt, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl group, fluorine Chemical C1-C 20 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, Cyclooctyl group, adamantanyl group, norbornanyl group (bicyclo[2.2.1]heptyl) ethyl group), norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, chloro[2.2.2]octyl group, (C1-C 20 alkyl)cyclopentyl group, (C1- C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C 1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 Alkyl)norbornenyl Group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 (Alkyl)cyclohe Xenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl) Bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1] Hexyl group, (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20 alkyl)phenyl group, biphenyl group, terphenyl group , naphthyl group, 1,2,3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl C-C substituted with a group, or any combination thereof 20 Alkyl group or C1-C2 0 alkoxy groups, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Phosphate group or its salt, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl group, fluorine Chemical C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group Sil group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, biphenyl group Cyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2. 2.2] octyl group, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 Al cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1 -C 20 alkyl)cyclopentenyl group, (C1-C 20 (Alkyl)cyclohexenyl group , (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[ 1.1.1]pentyl group, (C1-C 20 (Alkyl)bicyclo[2.1.1]hexyl group , (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a fluorenyl group, a phenanthrenyl group, Anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group aryl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazolyl group indolyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazinyl group Zolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinox Salinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group , benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group aryl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group aryl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophene group nyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazolyl group, Dazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothio phenyl groups, or any combination thereof, substituted or unsubstituted, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, nor Bornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cyclohexenyl group butenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, Bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C1-C 20 Archi phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetraphenyl group Hydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluora phenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group a phenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quino quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group , cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azaka a rubazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, or -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)( Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9) or -P(Q8)(Q9 ), and Q1 to Q9 are independent of each other. -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, - CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCD H2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2, or Ruiha Deuterium, C1-C 20substituted with alkyl groups, phenyl groups, or any combination thereof or unsubstituted n-propyl, isopropyl, n-butyl, or sec-butyl group , isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group pentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group The alkyl group may be a phenyl group, a biphenyl group, or a naphthyl group.

[0036] According to one embodiment, in Formulas 2 and 3, R, R, and R 31 ~R 33 are mutually independently hydrogen, deuterium, -F, cyano, substituted or unsubstituted C-C 20 Alkyl Groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1- C 10 Heterocycloalkyl group, phenyl group, biphenyl group, -Si(Q3)(Q4)( Q5), or -Ge(Q3)(Q4)(Q5). According to another embodiment, in Formulas 2 and 3, R, R, and R 31 ~R 33 are mutual Independently, hydrogen, deuterium, -F, or a cyano group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, a biphenyl group, or any of them; Substituted or unsubstituted C1-C in combination 20 Alkyl groups, C3-C 10 Cycloal Kill group, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group, or teeth -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0037] According to still another embodiment, Chemical Formula 2 is represented by the following <Condition 1-1> or <Condition 1- 2> can be satisfied. <Condition 1-1> R2 does not include a fluoro group (-F) or a cyano group. <Condition 1-2> R2 is hydrogen or deuterium; Deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 Haitai substituted with a cycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof; or unsubstituted, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group; -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0038] According to still another embodiment, Chemical Formula 2 satisfies the following <Condition 2-1> and <Condition 2-2>. > or <Conditions 2-3> can be satisfied. <Condition 2-1> At least one of the a2 R2 is a fluoro group (-F), a cyano group, or any of these. Any combination is included. <Condition 2-2> At least one of the a2 R2s is a fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl groups, C3-C 10 Cycloalkane group, C1-C 10 heterocycloalkyl group, phenyl group, biphenyl group, or any of these groups Fluorinated C1-C, substituted or unsubstituted in any combination 20 Alkyl groups, fluorinated C3 -C 10 Cycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, fluorinated phenyl groups C1-C containing phenyl, fluorinated biphenyl, and cyano groups 20 Alkyl group, cyano group-containing C3- C 10 Cycloalkyl groups, cyano-containing C1-C 10 Heterocycloalkyl group, cyano group a phenyl group containing a cyano group, or a biphenyl group containing a cyano group. <Condition 2-3> R2 is hydrogen, deuterium, -F, or a cyano group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, a biphenyl group, or any of them; Substituted or unsubstituted C1-C in combination 20 Alkyl groups, C3-C 10 Cycloal Kill group, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group, or teeth -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), At least one of the a2 R2's is a fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl groups, C3-C 10 Cycloalkane group, C1-C 10 heterocycloalkyl group, phenyl group, biphenyl group, or any of these groups Fluorinated C1-C, substituted or unsubstituted in any combination 20 Alkyl groups, fluorinated C3 -C 10Cycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, fluorinated phenyl groups C1-C containing phenyl, fluorinated biphenyl, and cyano groups 20 Alkyl group, cyano group-containing C3- C 10 Cycloalkyl groups, cyano-containing C1-C 10 Heterocycloalkyl group, cyano group a phenyl group containing a cyano group, or a biphenyl group containing a cyano group.

[0039] According to yet another embodiment, in Formula 2, ring CY2 is not a naphthalene group (e.g., For example, in Chemical Formula 2, the ring CY2 is a benzene group, a dibenzofuran group, a dibenzothiophene group, carbazole group or fluorene group), Chemical Formula 2 is <Condition 1-1> or <Condition 1 -2> can be satisfied. According to yet another embodiment, in Formula 2, ring CY2 is a naphthalene group, and 2 can satisfy either <Condition 1-1> or <Condition 1-2>. According to yet another embodiment, in Formula 2, ring CY2 is a naphthalene group, and 2 may satisfy <Condition 2-1>, <Condition 2-2>, or <Condition 2-3>.

[0040] According to yet another embodiment, in Formulas 2 and 3, R, R, and R 31 ~R 33 teeth , independently of each other, hydrogen or deuterium, Deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 Haitai substituted with a cycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof; or unsubstituted, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group; -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0041] For example, in Formulas 2 and 3, R1, R2, and R 31 ~R 33 are independent of each other, hydrogen, deuterium, cyano group, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, a group represented by one of the following chemical formulas 9-1 to 9-39 , At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with deuterium. The group At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with -F. The selected group, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with a cyano group. The substituted group, A group represented by one of the following chemical formulas 9-201 to 9-233, At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is deuterium. a group substituted with At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 9-201 to 9-233 is cyano. a group substituted with a group, A group represented by one of the following chemical formulas 10-1 to 10-126, At least one hydrogen in one of the chemical formulas 10-1 to 10-126 shown below is deuterium a group substituted with At least one hydrogen atom in one of the chemical formulas 10-1 to 10-126 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 10-1 to 10-126 is cyano. a group substituted with a group, A group represented by one of the following chemical formulas 10-201 to 10-343, At least one hydrogen atom in one of the following chemical formulas 10-201 to 10-343 is heavy. groups substituted with hydrogen, At least one hydrogen atom in one of the chemical formulas 10-201 to 10-343 shown below is - a group substituted with F, At least one hydrogen atom in one of the chemical formulas 10-201 to 10-343 shown below is substituted with silyl group. A group substituted with an aryl group, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5) (where Q3 For explanations of Q1 to Q5, please refer to the descriptions in this specification. .

[0042] As yet another example, T1 in Formula 2 is -F, -CF3, -CF2H, -CFH2, cyano group, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with -F. The selected group, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with a cyano group. The substituted group, At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 9-201 to 9-233 is cyano. a group substituted with a group, At least one hydrogen atom in one of the chemical formulas 10-1 to 10-126 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 10-1 to 10-126 is cyano. a group substituted with a group, At least one hydrogen atom in one of the chemical formulas 10-201 to 10-343 shown below is - a group substituted with F, Or at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-343 may be a group substituted with a cyano group.

[0043] As yet another example, R2 in Formula 2 can be hydrogen, deuterium, -CH3, -CD3, -CD 2H, -CDH2, A group represented by one of the following chemical formulas 9-1 to 9-39, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with deuterium. The group A group represented by one of the following chemical formulas 9-201 to 9-233, At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is deuterium. a group substituted with A group represented by one of the following chemical formulas 10-1 to 10-126, At least one hydrogen in one of the chemical formulas 10-1 to 10-126 shown below is deuterium a group substituted with A group represented by one of the following chemical formulas 10-201 to 10-343, At least one hydrogen atom in one of the following chemical formulas 10-201 to 10-343 is heavy. groups substituted with hydrogen, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5) (where Q3 For explanations of Q1 to Q5, please refer to the descriptions in this specification. .

[0044] As yet another example, in Formula 2, R2 can be hydrogen, deuterium, a cyano group, -F, -CH3 , -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, A group represented by one of the following chemical formulas 9-1 to 9-39, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with deuterium. The group At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with -F. The selected group, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with a cyano group. The substituted group, A group represented by one of the following chemical formulas 9-201 to 9-233, At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is deuterium. a group substituted with At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 9-201 to 9-233 is cyano. a group substituted with a group, A group represented by one of the following chemical formulas 10-1 to 10-126, At least one hydrogen in one of the chemical formulas 10-1 to 10-126 shown below is deuterium a group substituted with At least one hydrogen atom in one of the chemical formulas 10-1 to 10-126 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 10-1 to 10-126 is cyano. a group substituted with a group, A group represented by one of the following chemical formulas 10-201 to 10-343, At least one hydrogen atom in one of the following chemical formulas 10-201 to 10-343 is heavy. groups substituted with hydrogen, At least one hydrogen atom in one of the chemical formulas 10-201 to 10-343 shown below is - a group substituted with F, At least one hydrogen atom in one of the chemical formulas 10-201 to 10-343 shown below is substituted with silyl group. A group substituted with an aryl group, -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), At least one of the a2 R2 is -F, -CF3, -CF2H, -CFH2, sia Nomoto, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with -F. The selected group, At least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is replaced with a cyano group. The substituted group, At least one hydrogen atom in one of the chemical formulas 9-201 to 9-233 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 9-201 to 9-233 is cyano. a group substituted with a group, At least one hydrogen atom in one of the chemical formulas 10-1 to 10-126 shown below is -F. substituted groups, At least one hydrogen atom in one of the following chemical formulas 10-1 to 10-126 is cyano. a group substituted with a group, At least one hydrogen atom in one of the chemical formulas 10-201 to 10-343 shown below is - a group substituted with F, Or at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-343 may be a group substituted with a cyano group.

[0045] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0046] Chemical formula 9-1~9-39, 9-201~9-233, chemical formula 10-1~10-126, In chemical formulas 10-201 to 10-343, * indicates the bonding site with the adjacent atom, and Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylge It is a methyl group.

[0047] "A group in which at least one hydrogen atom in the chemical formulas 9-1 to 9-39 has been replaced with a deuterium atom" , and "Chemical formula 9-201 to 9-233, at least one hydrogen is replaced with deuterium The "group" may be, for example, a group represented by the following chemical formulae 9-501 to 9-514 and 9-601 to 9-609. It may be a group represented by -635. [ka] [ka] [ka]

[0048] "A group in which at least one hydrogen atom in the chemical formulas 9-1 to 9-39 is substituted with -F" and "Groups of the chemical formulas 9-201 to 9-233 in which at least one hydrogen atom is replaced by -F." can be, for example, groups represented by the following chemical formulas 9-701 to 9-710. [ka]

[0049] In chemical formulas 10-1 to 10-12, at least one hydrogen atom is replaced by a deuterium atom. "Groups in which at least one hydrogen atom is replaced by a deuterium atom" and "Groups in which at least one hydrogen atom is replaced by a deuterium atom in the chemical formulas 10-201 to 10-343" The "substituted group" is, for example, a group represented by the following chemical formulas 10-501 to 10-553. It could be. [ka] [ka] [ka]

[0050] In chemical formulas 10-1 to 10-126, at least one hydrogen atom is replaced by -F. "Group" and "Chemical formula 10-201 to 10-343, in which at least one hydrogen is replaced by -F" The "group" is, for example, a group represented by the following chemical formulas 10-601 to 10-615. It is possible. [ka]

[0051] In chemical formula 2, a1 and a2 represent the numbers of R1 and R2, respectively, and may independently be an integer from 0 to 10. When a1 is 2 or more, the two or more R1's may be the same or different. When a2 is 2 or more, the two or more R2 may be the same or different. good. For example, in Chemical Formula 2, a1 is an integer of 0-3. As another example, in Chemical Formula 2, a2 ​​is an integer from 0 to 6. According to one embodiment, in Formula 2, a2 ​​is 1 or 2. According to another embodiment, in Formula 2, a2 ​​is 1 or 2 and R2 is not hydrogen. .

[0052] In Chemical Formulas 2 and 3, * and *' are binding sites with Ir in Chemical Formula 1, respectively. According to yet another embodiment, the organometallic compound of Formula 1 comprises at least one deuterium. According to yet another embodiment, at least one of the a1 R1 in Formula 1 is at least It may contain at least one deuterium. According to yet another embodiment, at least one of the a2 R2 in Formula 1 is deuterium oxide. It may contain elements. According to yet another embodiment, at least one of the a2 R2 in Formula 1 is C1 -C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkane deuterated C1-C substituted or unsubstituted alkyl groups, or any combination thereof; 20 a Alkyl group, deuterated C3-C 10 Cycloalkyl groups or deuterated C1-C 10 Heterogeneity It may be a cycloalkyl group.

[0053] In chemical formulas 2 and 3, 1) Two or more of the a1 R1 may optionally be bonded to each other, and at least one R 1a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Replace with or unsubstituted C1-C 30 can form a heterocyclic group, 2) Two or more of the a2 R2s may optionally be bonded to each other, and at least one R1 a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Replace with or unsubstituted C1-C 30 can form a heterocyclic group, 3) In R1 and R2, two or more may optionally be bonded to each other, and at least one R 1a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Replace with or unsubstituted C1-C 30 can form a heterocyclic group, 4) R 31 ~R 33 In the formula, two or more are optionally bonded to each other, and at least one R1a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 1a Place Substituted or unsubstituted C1-C 30 A heterocyclic group can be formed. R 1a For the explanation of R1, refer to the explanation of R1 in this specification.

[0054] According to one embodiment, in Formula 2: The group represented by TIFF2026042033000035.tif36128 may be a group represented by one of the following chemical formulas 2-1 to 2-21: . [ka] [ka] [ka] [ka]

[0055] Chemical formulas 2-1 to 2-21: Y1 is N, X1~X 10 are independently C or N, but are not limited to the chemical formulas 2-1 to 2-9, and at least one of X1 to X8 in Chemical Formula 2-21 is C; -20 X1~X 10 at least one of is C, * is a binding site with Ir in Chemical Formula 1, *" is a bonding site with an adjacent atom. For example, X1~X 10 can be C.

[0056] According to another embodiment, in Formula 2: The group represented by TIFF2026042033000040.tif45145 is a group represented by one of the following chemical formulas 2(1) to 2(75): obtain. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0057] Chemical formulas 2(1) to 2(75) Y1 is N, X 11 is C(R 11 ) or N, and X 12 is C(R 12 ) or N, and X 13 is C(R 13 ) or N, and X 14 is C(R 14 ) or N, and X 15 is C( R 15 ) or N, and X 16 is C(R 16 ) or N, and X 17 is C(R 17 ) or N and X 18 is C(R 18 ) or N, and X 19 is C(R 19 ) or N Yes, X 19a is C(R 19a ) or N, R 11 ~R 19 , and R 19a The explanations for R1 and R2 are given in the present specification. Please refer to the explanation about T 11 and T 12 The explanations for T1 and T2 are given in the present specification. Refer to * is a binding site with Ir in Chemical Formula 1, *" is a bonding site with an adjacent atom.

[0058] According to yet another embodiment, in Formula 2: The group represented by TIFF2026042033000050.tif38145 is a group represented by one of the chemical formulas CY2-1 to CY2-10 shown below. could be. [ka] [ka]

[0059] Chemical formulas CY2-1 to CY2-10 Y2 is C, X 21 are O, S, N(R7), C(R 27 )(R 28 ), or Si(R 27 )(R2 8) and R 21 ~R 28 The explanations for R2 in this specification are the same as those for R2. See, *' is the binding site with Ir in Chemical Formula 1, *" is a bonding site with an adjacent atom in chemical formula 1. For example, in chemical formula 2, The group represented by TIFF2026042033000053.tif38145 may be a group represented by chemical formula CY2-1 or CY2-8.

[0060] According to another embodiment, in Formula 2: The group represented by TIFF2026042033000054.tif38145 is represented by the following chemical formulae CY2-1(1) to CY2-1(3) and chemical formula C It may be a group represented by one of Y2-8(1) to CY2-8(6). [ka]

[0061] for example, i) Chemical formula CY2-1 and chemical formulas CY2-1(1) to CY2-1(3), R 21 Reach BiR 23 , and ii) Chemical formula CY2-8(1) to CY2-8(6), R 23 ~R 28 are independent of each other and deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof; Substituted or unsubstituted C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1 -C 10 It may also be a heterocycloalkyl group, a phenyl group, or a biphenyl group.

[0062] Another example is i) Chemical formula CY2-1 and chemical formulas CY2-1(1) to CY2-1(3), R21 Reach BiR 23 , and ii) Chemical formula CY2-8(1) to CY2-8(6), R 23 ~R 28 are independent of each other and deuterium, C1-C 20 alkyl groups, or any combination thereof, Unsubstituted C1-C 20 It may be an alkyl group.

[0063] Yet another example is the compound of formula CY2-1, 22 and R 24 are independent of each other, It can be hydrogen or deuterium. Further examples include compounds of formula CY2-1 and CY2-1(1), where R 21 and R 23 teeth , may be identical to each other. Further examples include compounds of formula CY2-1 and CY2-1(1), where R 21 and R 23 teeth , may be different from each other. Further examples include compounds of formula CY2-1 and CY2-1(1), where R 21 and R 23 teeth , are different from each other, and R 23 The number of carbon atoms in 21 From the number of carbon atoms contained in There will also be more.

[0064] As yet another example, i) R of the chemical formula CY2-1 21 ~R 24 At least one of the ii) R of chemical formulas CY2-2 to CY2-7 21 ~R 26 At least one of the iii) R of the chemical formula CY2-8 23 ~R 28 At least one of the iv) R of the chemical formula CY2-921 , R 24 ~R 28 One of these, or any combination thereof Combination, v) R of the chemical formula CY2-10 21 , R 22 , R 25 ~R 28 One of these Any combination, vi) Chemical formula CY2-1(1) to CY2-1(3), R 21 and R 23 , and vii) Chemical formula CY2-8(1) to CY2-8(6), R 23 ~R 28 are independent of each other, C1-C 20 Alkyl groups, C3-C 10 Cycloa alkyl group, C1-C 10 a heterocycloalkyl group, a phenyl group, a biphenyl group, or Deuterated C1-C, substituted or unsubstituted in any combination of 20 Alkyl groups, heavy water Chemical C3-C 10 Cycloalkyl groups, deuterated C1-C 10 heterocycloalkyl groups, or can be a deuterated phenyl group.

[0065] As yet another example, i) Chemical formula CY2-1, R 21 and R 23 At least one of (e.g., chemical formula C Y2-1, R 21 and R 23 ), ii) Chemical formula CY2-1(1) to CY2-1(3), R 21 and R 23 , and iii) Chemical formula CY2-8(1) to CY2-8(6), R 23 ~R 28 are independent of each other, C1-C 20 Alkyl groups, C3-C10 Cycloa alkyl group, C1-C 10 a heterocycloalkyl group, a phenyl group, a biphenyl group, or Deuterated C1-C, substituted or unsubstituted in any combination of 20 Alkyl groups, heavy water Chemical C3-C 10 Cycloalkyl groups, deuterated C1-C 10 heterocycloalkyl groups, or can be a deuterated phenyl group.

[0066] As yet another example, i) R of the chemical formula CY2-8 23 ~R 28 , ii) R of the chemical formula CY2-9 21 , and R 24 ~R 28 , and iii) R of the chemical formula CY2-10 21 , R 22 , and R 25 ~R 28 teeth, Independently of each other, hydrogen or deuterium, Deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 Haitai substituted with a cycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof; or unsubstituted, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group; -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0067] As yet another example, i) R of the chemical formula CY2-8 23 ~R 28 , ii) R of the chemical formula CY2-9 21 , and R 24 ~R 28 , and iii) R of the chemical formula CY2-10 21 , R 22 , and R 25 ~R 28 teeth, Independently of each other, hydrogen, deuterium, -F, or a cyano group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, a biphenyl group, or any of them; Substituted or unsubstituted C1-C in combination 20 Alkyl groups, C3-C 10 Cycloal Kill group, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group, or teeth -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5), i) R of the chemical formula CY2-8 23 ~R 28 At least one of the ii) R of the chemical formula CY2-9 21 , R 24 ~R 28 One of these, or any combination thereof combination, and iii) R of the chemical formula CY2-10 21 , R 22 , R 25 ~R 28 One of the following Any combination of these is Independently of each other, a fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl groups, C3-C 10 Cycloalkane group, C1-C 10heterocycloalkyl group, phenyl group, biphenyl group, or any of these groups Fluorinated C1-C, substituted or unsubstituted in any combination 20 Alkyl groups, fluorinated C3 -C 10 Cycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, fluorinated phenyl groups C1-C containing phenyl, fluorinated biphenyl, and cyano groups 20 Alkyl group, cyano group-containing C3- C 10 Cycloalkyl groups, cyano-containing C1-C 10 Heterocycloalkyl group, cyano group The phenyl group may be a phenyl group containing a cyano group, or a biphenyl group containing a cyano group.

[0068] Further examples include R 23 ~R 28 teeth , independently of each other, a fluoro group (-F) or a cyano group, or Deuterium, fluoro group, cyano group, C1-C 20 Alkyl groups, C3-C 10 Cycloalkane group, C1-C 10 heterocycloalkyl group, phenyl group, biphenyl group, or any of these groups Fluorinated C1-C, substituted or unsubstituted in any combination 20 Alkyl groups, fluorinated C3 -C 10 Cycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, fluorinated phenyl groups C1-C containing phenyl, fluorinated biphenyl, and cyano groups 20 Alkyl group, cyano group-containing C3- C 10 Cycloalkyl groups, cyano-containing C1-C 10 Heterocycloalkyl group, cyano group The phenyl group may be a phenyl group containing a cyano group, or a biphenyl group containing a cyano group. According to yet another embodiment, R of Formula 331 and R 32 The number of carbon atoms contained in Each is also 4 or more (e.g., 5 or more).

[0069] According to yet another embodiment, the organometallic compound represented by Formula 1 can be prepared by the following conditions: Condition 4, Condition 5, or a combination thereof may be satisfied. <Condition 4> In formula 3, R 31 is a group represented by the following chemical formula 4. <Condition 5> In formula 3, R 32 is a group represented by the following chemical formula 5. [ka] [ka] In Chemical Formulae 4 and 5, A1 to A6 are each independently hydrogen or deuterium, or Deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl groups, biphenyls C-C substituted or unsubstituted phenyl groups, or any combination thereof 20 Archi group, C3-C 10 Cycloalkyl groups, C6-C 60 Aryl groups, C1-C 60 Heteroa an aryl group, a phenyl group, or a biphenyl group; * indicates a bonding site with an adjacent atom.

[0070] For example, chemical formula 4 satisfies one of the following conditions 4-1 to 4-6. and / or Chemical Formula 5 satisfies one of the following <Condition 5-1> to <Condition 5-6>. possible. <Condition 4-1> A1 to A3 are not hydrogen at the same time. <Condition 4-2> A1 to A3 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 Shik and substituted or unsubstituted with alkyl, phenyl, biphenyl, or any combination thereof. is unsubstituted, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl groups, or is a biphenyl group. <Condition 4-3> A1 and A2 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Unsubstituted C1-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, phenyl groups, or a biphenyl group, A3 is deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl C2-C2 substituted or unsubstituted with a group, a biphenyl group, or any combination thereof 0 alkyl groups, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-4> A1 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloal substituted or unsubstituted alkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Conversion, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl group, phenyl group or biphenyl group is a methyl group, A2 and A3 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Unsubstituted, C2-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, phenyl groups, Or a biphenyl group. <Condition 4-5> A1 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3; A2 is deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl C1-C2 substituted or unsubstituted with a group, a biphenyl group, or any combination thereof 0 alkyl groups, C3-C 10 a cycloalkyl group, a phenyl group, or a biphenyl group; A3 is deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl C2-C2 substituted or unsubstituted with a group, a biphenyl group, or any combination thereof 0 alkyl groups, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-6> A1 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3; A2 and A3 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Unsubstituted, C2-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, phenyl groups, Or a biphenyl group.

[0071] <Condition 5-1> A4 to A6 are not hydrogen at the same time. <Condition 5-2> A4 to A6 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 Shik and substituted or unsubstituted with alkyl, phenyl, biphenyl, or any combination thereof. is unsubstituted, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl groups, or is a biphenyl group. <Condition 5-3> A4 and A5 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Unsubstituted C1-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, phenyl groups, or a biphenyl group, A6 is deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl C2-C2 substituted or unsubstituted with a group, a biphenyl group, or any combination thereof 0 alkyl groups, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-4> A4 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloal substituted or unsubstituted alkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Conversion, C1-C 20 Alkyl groups, C3-C 10 a cycloalkyl group, a phenyl group, or a biphenyl group is a phenyl group, A5 and A6 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Unsubstituted, C2-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, phenyl groups, Or a biphenyl group. <Condition 5-5> A4 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3; A5 is deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl C1-C2 substituted or unsubstituted with a group, a biphenyl group, or any combination thereof 0 alkyl groups, C3-C 10 a cycloalkyl group, a phenyl group, or a biphenyl group; A6 is deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenyl C2-C2 substituted or unsubstituted with a group, a biphenyl group, or any combination thereof 0 alkyl groups, C3-C 10 It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-6> A4 is hydrogen, deuterium, -CH3, -CH2D, -CHD2, or -CD3; A5 and A6 are independently deuterium, C1-C 20 Alkyl groups, C3-C 10 S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Unsubstituted, C2-C 20 Alkyl groups, C3-C 10 cycloalkyl groups, phenyl groups, Or a biphenyl group.

[0072] According to yet another embodiment, R of Formula 3 31 ~R 33 At least one of the Independently, deuterium, C1-C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, phenoxy groups C3-C substituted or unsubstituted with phenyl, biphenyl, or any combination thereof 10 It is also a cycloalkyl group. According to yet another embodiment, the organometallic compound represented by Formula 1 is the compound shown below: It can be one of items 1-19. [ka] [ka]

[0073] According to one embodiment, the emission spectrum or electron density of the organometallic compound represented by Chemical Formula 1 The FWQM of the emission peak of the electroluminescence (EL) spectrum is less than 100 nm. . For example, the emission spectrum or electroluminescence spectrum of an organometallic compound FWQM of optical peak: 100nm or less, 60nm to 100nm, 70nm to 100nm , 80 nm to 100 nm, or 82 nm to 96 nm. On the other hand, according to another embodiment, the emission spectrum or is the maximum emission wavelength (emission peak wavelength (λ max )) is in the range of 600 nm to 660 nm or 615 nm to 640 nm. For example, the emission spectrum or electroluminescence spectrum of an organometallic compound The maximum emission wavelength of the light peak (λ max )) is 615nm~630nm or is in the range of 620nm to 630nm.

[0074] The horizontal orientation rate of the transition dipole moment (TDM) of the organometallic compound represented by chemical formula 1 is , 90% to 100%. For example, the horizontal orientation ratio of the transition dipole moment (TDM) of an organometallic compound is, for example, 90%~99%, 90%~98%, 90%~97%, 90%~96%, 90%~95%, Or 91% to 95%. The horizontal orientation rate of the transition dipole moment (TDM) of an organometallic compound can be measured by, for example, Reference can be made to Evaluation Example 3 described below. As mentioned above, the transition dipole moment (TDM) of organometallic compounds has a high horizontal orientation rate. Therefore, when an organic light emitting device including an organometallic compound is driven, the film including the organometallic compound The electric field is emitted in a direction that is substantially horizontal to the Optical loss due to polariton modes can be reduced. The extraction efficiency (i.e., An electronic device (e.g., a light-emitting layer described later) including a film containing an organometallic compound. For example, in organic light-emitting devices, the light emitted from the organometallic compound is extracted to the outside. Since the organic metal compound has a high luminescence efficiency, electronic devices using the organic metal compound, such as organic light-emitting devices, have a high luminescence efficiency. Light efficiency can be achieved.

[0075] The quantum photoluminescence efficiency (PLQY) in the film of the organometallic compound represented by chemical formula 1 film) is 90% to 100%. For example, the quantum luminescence efficiency of organometallic compound films is 91% to 100%, and 92%. %~100%, 93%~100%, 94%~100%, 95%~100%, 96%~10 0%, 97% to 100%, 98% to 100%, 99% to 100%, or 100%. According to one embodiment, the quantum luminescence efficiency of the film of the organometallic compound is 95% to 9 9%, 96%~99%, 97%~99%, 98%~99%.

[0076] The method for synthesizing the organometallic compound represented by Chemical Formula 1 can be easily understood by those skilled in the art by referring to the synthesis examples described below. It is something that can be recognized. Therefore, the organometallic compound represented by Chemical Formula 1 can be used in the organic layer of an organic light-emitting device, for example, and according to another aspect, the compound is suitable for use as a dopant in the light-emitting layer of the a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emitting layer; The organic layer comprises an organic polymer containing at least one organometallic compound represented by Chemical Formula 1. An optical element is provided.

[0077] The organic light-emitting device has an organic layer containing the organometallic compound represented by Chemical Formula 1 as described above. This results in low driving voltage, high external quantum efficiency, relatively small FWQM, and long lifetime. You can have life. The organometallic compound represented by Chemical Formula 1 is used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Chemical Formula 1 is contained in the light-emitting layer. In this case, the organometallic compound acts as a dopant, and the light-emitting layer further contains a host. (i.e., the content of the organometallic compound represented by Chemical Formula 1 is less than the content of the host. stomach). The light-emitting layer can emit red or green light.

[0078] In this specification, the phrase "(an organic layer) contains one or more organometallic compounds" means "( The organic layer is a metal organic compound of the formula I or a metal organic compound of the formula I It is also interpreted as meaning that the organometallic compound may contain two or more different organometallic compounds. For example, the organic layer may contain 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 contain Compound 1 and Compound 2 as organometallic compounds. At this time, Compound 1 and Compound 2 are present in the same layer (for example, Compound 1 and Compound 2 are Both may be present in the light-emitting layer.

[0079] The first electrode is an anode, which is a hole-injecting electrode, and the second electrode is a cathode, which is an electron-injecting electrode. Alternatively, the first electrode is a cathode, which is an electron injecting electrode, and the second electrode is , the anode, which is the hole injection electrode. For example, in an organic light-emitting device, the first electrode is an anode and the second electrode is a cathode. the organic layer comprises a hole transport region disposed between the first electrode and the light-emitting layer, and a hole transport region disposed between the light-emitting layer and the first electrode. The hole transport region further comprises a hole injection layer, a hole transport region, and an electron transport region disposed between the two electrodes. a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof; The region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. good. In this specification, the term "organic layer" refers to a layer between a first electrode and a second electrode in an organic light-emitting element. is a term that refers to single and / or multiple layers arranged in a The "organic layer" may include not only organic compounds but also organometallic complexes containing metals. .

[0080] FIG. 3 is a cross-sectional view showing a schematic configuration of an organic light-emitting device 10 according to one embodiment of the present invention. is. Hereinafter, with reference to FIG. 3, the structure and manufacturing method of an organic light emitting device according to an embodiment of the present invention will be described. The following explains the details: The organic light-emitting element 10 is a layered structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are stacked in this order. It has a structure.

[0081] A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a general organic light-emitting device can be used. Glass with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness A substrate or a transparent plastic substrate can be used.

[0082] The first electrode 11 is formed by depositing a material for the first electrode on the upper part of the substrate by vapor deposition or sputtering. It is formed by providing it using the law, etc. The first electrode 11 is an anode. The material for the first electrode may include a material having a high work function to facilitate hole injection. . The first electrode 11 is a reflective electrode, a semi-transparent electrode, or a transparent electrode. The first electrode material is indium tin oxide (ITO), indium zinc oxide (IZ), O), tin oxide (SnO2), zinc oxide (ZnO), etc. can be used. Or magnesium (Mg), aluminum (Al), aluminum-lithium (Al -Li), calcium (Ca), magnesium-indium (Mg-In), magnesium Metals such as mu-silver (Mg-Ag) can also be used. The first electrode 11 can have a single layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 can have a three-layer structure of ITO / Ag / ITO.

[0083] An organic layer 15 is disposed on top of the first electrode 11 . Organic layer 15 may include a hole transport region, an emissive layer, and an electron transport region. The hole transport region is disposed between the first electrode 11 and the light-emitting layer. The hole transport region may be a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any of these. It may include any combination. The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may be a hole injection layer / hole transport layer or a layer stacked in this order from the first electrode 11. The layer may have a structure of hole injection layer / hole transport layer / electron blocking layer. When the hole transport region includes a hole injection layer, the hole injection layer is vacuum-deposited on top of the first electrode 11. method, spin coating method, casting method, LB (Langmuir-Blodgett) It is formed using a variety of methods such as the law.

[0084] When the hole injection layer is formed by vacuum deposition, the deposition conditions are as follows: The thickness of the hole injection layer varies depending on the compound used, the structure of the hole injection layer, and the thermal properties. For example, the deposition temperature is about 100 to about 500°C, and the vacuum degree is about 10 -8 ~about 10 -3 torr, evaporation The speed is selected within the range of about 0.01 to about 100 Å / sec. When the hole injection layer is formed by spin coating, the coating conditions are as follows: Depending on the compound used as the injection layer material, the structure of the hole injection layer to be targeted, and the thermal properties, The coating speed varies, but is about 2,000 rpm to about 5,000 rpm. The heat treatment temperature for removing the solvent afterwards is selected from the temperature range of about 80°C to 200°C. .

[0085] The conditions for forming the hole transport layer and the electron blocking layer refer to the conditions for forming the hole injection layer. The hole transport region may be, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated -NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triflate phenylamine) (TCTA), polyaniline / dodecylbenzenesulfonic acid) (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonyl) PEDOT / PSS), Polyaniline / Camphorsulfonic Acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), bottom Compounds represented by the chemical formula 201 shown below, compounds represented by the chemical formula 202 shown below , or any combination thereof. TIFF2026042033000060.tif61163TIFF2026042033000061.tif104154 [ka] [ka]

[0086] In chemical formula 201, Ar 101 and Ar 102 are independently deuterium, -F, -Cl, -Br, -I , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C1 -C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C3-C10 a cycloalkenyl group, C1-C 10 Heterocycloalkyl groups, C1-C 10 Heterocycloalkenyl group, C6- C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1 -C 60 heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof, substituted or unsubstituted, phenylene group, pentalenylene group, group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylenylene group , naphthacenylene, picenylene, perylenylene, or pentacenylene groups. .

[0087] In formula 201, xa and xb are each independently an integer of 0 to 5, or 0, 1, or 2. It could be. For example, xa can be 1 and xb can be 0. In chemical formulas 201 and 202, R 101 ~R 108 , R 111 ~R 119 , and R 121 ~R 124 are independent of each other, Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfo Phosphate group or its salt, Phosphate group or its salt, C1-C 10 Alkyl groups (e.g., methyl groups, Ethyl, propyl, butyl, pentyl, hexyl, etc.) or C1-C 10 Al oxy groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy groups) etc.), Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or a salt thereof, a C1-C substituted with a phosphate group or a salt thereof, or any combination thereof 10 Alkyl group or C1-C 10 an alkoxy group, or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups, C1-C 10 alkoxy group or any combination thereof, substituted or unsubstituted, phenyl group, naphthyl group, aliphatic group, It may be an anthracenyl group, a fluorenyl group, or a pyrenyl group.

[0088] In chemical formula 201, R 109 represents deuterium, -F, -Cl, -Br, -I, and hydroxyl groups. , cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carvone Acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl group, C1-C 20 Alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyridinyl group phenyl, naphthyl, or any combination thereof, substituted or unsubstituted; , an anthracenyl group, or a pyridinyl group.

[0089] According to one embodiment, the compound of formula 201 has formula 201A shown below: Therefore, it can also be expressed as [ka] In chemical formula 201A, R 101 , R 111 , R 112 and R 109 For a detailed explanation of , see above.

[0090] For example, the hole transport region may be one of the compounds HT1 to HT21 shown below, or one of these compounds. may include any combination of: [ka] [ka] [ka] [ka] [ka]

[0091] The thickness of the hole transport region is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1, 000Å. The hole transport region may be a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof. If the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 10 The thickness of the hole transport layer is about 50 Å to about 2,000 Å, for example. , about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-mentioned ranges, Thus, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage. In addition to the materials mentioned above, the hole transport region may further contain a charge generating material to improve conductivity. may be included in. The charge generating material can be uniformly or non-uniformly distributed within the hole transport region.

[0092] The charge generating material is, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any of these. It can be a combination of: For example, the p-dopant is tetracyanoquinone dimethane (TCNQ), 2,3,5,6 -Tetrafluorotetracyano-1,4-benzoquinone dimethane (F4-TCNQ), F Quinone derivatives such as 6-TCNNQ, tungsten oxides and molybdenum oxides metal oxides, cyano-containing compounds such as compound HT-D1 shown below, or It can be any combination. TIFF2026042033000070.tif103128

[0093] The hole transport region may further include a buffer layer. The buffer layer compensates for the optical resonance distance due to the wavelength of the light emitted from the light emitting layer, thereby improving efficiency. It can play a role in raising the On the other hand, when the hole transport region includes an electron blocking layer, the electron blocking layer material is a material that can be used to inhibit the hole transport as described above. The materials may include materials that may be used in the transport region, host materials described below, or any combination thereof. obtain. For example, when the hole transport region includes an electron blocking layer, the electron blocking layer material may be mC P, the compound HT21, or any combination thereof can be used.

[0094] On top of the hole transport region, methods such as vacuum deposition, spin coating, casting, and LB method are used. The light-emitting layer can be formed by using such a method. When forming the light-emitting layer by vacuum deposition or spin coating, the deposition conditions and The coating conditions vary depending on the compound used, but generally, the formation of the hole injection layer is The condition is selected from a range of conditions substantially the same as the above. The light-emitting layer comprises a host and a dopant, the dopant being a compound as described herein. The organometallic compounds may include those represented by Formula 1.

[0095] The hosts are TPBi, TBADN, ADN (also known as "DNA"), and CBP, as shown below. , CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, or any of them may include any combination of: TIFF2026042033000071.tif96162TIFF2026042033000072.tif82162

[0096] When the organic light emitting device is a full-color organic light emitting device, the light emitting layer may be a red light emitting layer, a green light emitting layer, a The blue light-emitting layer and / or the blue light-emitting layer are patterned. Alternatively, the light-emitting layer has a structure in which a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer are stacked. By doing so, it is possible to emit white light. do. When the light-emitting layer includes a host and a dopant, the content of the dopant is generally about 1 / 2 of the host. The amount is selected from the range of about 0.01 to about 15 parts by weight based on 100 parts by weight. The thickness of the light-emitting layer is about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. do. When the thickness of the light-emitting layer satisfies the above-mentioned range, excellent light-emitting properties can be obtained without a substantial increase in driving voltage. It can exhibit excellent luminescence properties.

[0097] An electron transport region is then placed on top of the light emitting layer. The electron transport region may be a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. It may include For example, the electron transport region may be a hole blocking layer / electron transport layer / electron injection layer or an electron transport layer / electron It can have an injection layer structure. The electron transport layer may have a single layer structure or a multilayer structure containing two or more different materials. This can be done. The conditions for forming the hole blocking layer, electron transport layer and electron injection layer in the electron transport region are determined by the shape of the hole injection layer. Refer to the conditions for the

[0098] When the electron transport region includes a hole blocking layer, the hole blocking layer may be, for example, BCP, BPhen, BAlq, or any combination thereof. [ka]

[0099] Alternatively, the hole blocking layer may be formed from a host, an electron transport layer material described later, an electron injection layer material, or any of these. may include any combination of: The thickness of the hole blocking layer is about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. do. When the thickness of the hole blocking layer satisfies the above range, the driving voltage does not increase substantially. , excellent hole blocking properties can be obtained.

[0100] The electron transport layer is made of BCP, BPhen, Alq3, BAlq, TAZ, NTAZ, or any of its It may include any combination of these. TIFF2026042033000074.tif88147

[0101] Alternatively, the electron transport layer may contain at least one of the following compounds ET1 to ET25 and It may include any combination of these. [ka] [ka] [ka] [ka]

[0102] The thickness of the electron transport layer is about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. is. When the thickness of the electron transport layer satisfies the above range, the driving voltage does not increase substantially. As a result, satisfactory electron transport properties can be obtained. The electron transport layer may further contain a metal-containing material in addition to the materials described above.

[0103] The metal-containing material may include a Li complex. The Li complex may include, for example, compounds ET-D1 or ET-D2 shown below. [ka]

[0104] The electron transport region may also include an electron injection layer to facilitate electron injection from the second electrode 19. do. The electron injection layer may be made of LiF, NaCl, CsF, Li2O, BaO, or any combination thereof. It may include a combination. The thickness of the electron injection layer is about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above-mentioned range, the driving voltage does not increase substantially. As a result, satisfactory electron injection characteristics can be obtained.

[0105] A second electrode 19 is disposed on top of the organic layer 15 . The second electrode 19 is the cathode. The material for the second electrode 19 may be a metal, alloy, or conductive material having a relatively low work function. Compounds, or combinations thereof can be used. Specific examples include lithium (Li), magnesium (Mg), and aluminum (Al ), aluminum-lithium (Al-Li), calcium (Ca), magnesium-in Magnesium (Mg-In), magnesium-silver (Mg-Ag), etc. are used as the material for forming the second electrode 19. Can be used as a texture. Alternatively, to obtain a front light emitting element, a transparent second electrode 19 is formed using ITO or IZO. A variety of modifications are possible, such as the above.

[0106] The organic light-emitting device has been described above with reference to FIG. 3, but it is not limited thereto. do not have. According to yet another aspect, the organic light emitting devices can also be included in electronic devices. Accordingly, an electronic device is provided that includes an organic light emitting device. The electronic devices may include, for example, displays, lights, sensors, and the like.

[0107] As used herein, C5-C 30 A carbocyclic group is a ring-forming group having 5 to 30 carbon atoms. It represents a saturated or unsaturated ring group having only one ring. C5-C 30 A carbocyclic group may be a monocyclic or polycyclic group. "(At least one R 1a (substituted or unsubstituted) C5-C 30 "Carbocyclic group" is, for example, For example, (at least one R 1aadamantane group, norbornane group, Nanone group (bicyclo[2.2.1]heptane group), norbornene group, bicyclo[1.1.1 ]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group , cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group , anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1, Contains 2,3,4-tetrahydronaphthalene group, cyclopentadiene group, fluorene group, etc. It can be seen.

[0108] As used herein, C1-C 30 The heterocyclic group has 1 to 30 carbon atoms as ring atoms. In addition, the compound may contain at least one heteroatom selected from N, O, P, Si, S, Ge, Se, and B. It represents a saturated or unsaturated ring group having at least one ring. C1-C 30 The heterocyclic group is a monocyclic group or a polycyclic group. "(At least one R 1a "C1-C30 heterocyclic group substituted or unsubstituted with" means For example, (at least one R 1a substituted or unsubstituted thiophene group, furan group , pyrrole group, silole group, borole group, phosphole group, selenophene group, germole group , benzothiophene group, benzofuran group, indole group, benzosilole group, benzoboro group benzoyl group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiazolinone group, olefin group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborane group dibenzophosphole group, dibenzoselenophene group, dibenzogermol group, dibenzo Dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5, 5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, Azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, Azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group , azadibenzogermole group, azadibenzothiophene 5-oxide group, aza-9H-thiophene Fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, imidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, Triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiazole group Diazolyl group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, It may include a dihydroquinoline group, etc.

[0109] As used herein, C1-C 60 The alkyl group is a linear or branched saturated alkyl group having 1 to 60 carbon atoms. means a monovalent aliphatic hydrocarbon radical, C1-C 60 The alkylene group is C1-C 60 Alkyl The term "a" refers to a divalent group having the same structure as the group. As used herein, C1-C 60 Alkyl groups, C1-C 20 Alkyl group and / or C1 -C10 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group , tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3- Pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group Silyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, te rt-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or any of these methyl, ethyl, n-propyl, iodo, ... isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group , sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, se c-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group Octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, t ert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, or tert-decyl group Sil groups and the like may be included. For example, formula 9-33 is a branched C6 alkyl group substituted with two methyl groups. This can be seen as a tert-butyl group.

[0110] As used herein, C1-C 60 The alkoxy group is -OA. 101 (where A 101 teeth , C1-C 60 means a monovalent group having the formula: As used herein, C1-C 60 Alkoxy groups, C1-C 20 Alkoxy group or C1 -C 10 Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or may include a pentoxy group. As used herein, C3-C 10 Cycloalkyl groups are C3-C 10 Monovalent saturated hydrocarbons means a ring group, C3-C 10 The cycloalkylene group is C3-C 10 Cycloalkyl groups It means a divalent group having one structure. As used herein, C3-C 10 Examples of cycloalkyl groups include cyclopropyl groups, cycloalkyl groups, butyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group group, adamantanyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group xyl group, bicyclo[2.2.1]heptyl group (norbornanyl group), bicyclo[2.2 .2]octyl groups, etc.

[0111] As used herein, C1-C 10 Heterocycloalkyl groups include N, O, P, Si, S, At least one heteroatom selected from Ge, Se, and B is present as a ring-forming atom. Including C1-C 10 means a monovalent monocyclic group, C1-C 10 The heterocycloalkylene group is a C1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group. As used herein, C1-C 10 Examples of heterocycloalkyl groups include silolanyl groups, silyl groups, and silyl groups. Linanyl group, tetrahydrofuranyl group, tetrahydro-2H-pyranyl group, tetrahydro Thiophenyl groups and the like may be included. As used herein, C2-C 60 Alkenyl groups are C2-C 60 The middle or It has a structure containing one or more carbon-carbon double bonds at the terminal, and specific examples thereof include ethenyl. groups, propenyl groups, butenyl groups, and the like. As used herein, C2-C 60 The alkenylene group is C2-C 60 Same as alkenyl group means a divalent group having the structure:

[0112] As used herein, C2-C 60 Alkynyl groups are C2-C 60 The middle or It has a structure containing one or more carbon-carbon triple bonds at the terminal, and specific examples thereof include ethynyl groups, propynyl groups, and the like. As used herein, C2-C 60 The alkynylene group is C2-C 60 Same as alkynyl group means a divalent group having the structure: As used herein, C3-C 10 The cycloalkenyl group is C3-C 10 A monovalent monocyclic group It has at least one carbon-carbon double bond in the ring, but is aromatic. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cyclopentenyl group. cycloheptenyl groups, etc. As used herein, C3-C 10 The cycloalkenylene group is C3-C 10 Cycloalkane It means a divalent group having the same structure as a nyl group. As used herein, C1-C 10 Heterocycloalkenyl groups include N, O, P, Si, and S. At least one heteroatom selected from Ge, Se, and B is used as a ring-forming atom. C1-C 10 It is a monovalent monocyclic group having at least one double bond in the ring. C1-C 10 Specific examples of heterocycloalkenyl groups include 2,3-dihydrofuranyl groups, 2 , 3-dihydrothiophenyl group, etc. As used herein, C1-C 10 The heterocycloalkenylene group is a C1-C 10 Hetero It means a divalent group having the same structure as a cycloalkenyl group.

[0113] As used herein, C6-C 60 The aryl group is C6-C 60 Has a carbocyclic aromatic system means a monovalent group, C6-C 60 The arylene group is C6-C 60 Bicyclic aromatic rings means a valence group. C6-C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, and a phenyl group. Examples include an phenanthrenyl group, a pyrenyl group, and a chrysenyl group. C6-C 60 Aryl groups and C6-C 60 When the arylene group contains two or more rings, the two or more The upper rings may be fused together. As used herein, C7-C 60 The alkylaryl group has at least one C1-C6 C6-C substituted with alkyl groups 60 It means an aryl group. As used herein, C1-C 60 Heteroaryl groups include N, O, P, Si, S, Ge, containing at least one heteroatom selected from Se and B as a ring-forming atom; means a monovalent group having a C1-C60 cyclic aromatic system, C1-C 60 The heteroarylene group is At least one hetero element selected from the group consisting of N, O, P, Si, S, Ge, Se, and B Contains 1 atom as a ring atom, C1-C 60 means a divalent group having a carbocyclic aromatic system . C1-C 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, and pyrazinylated groups. These include a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. C1-C 60 Heteroaryl groups and C1-C 60 The heteroarylene group contains two or more rings. If desired, two or more rings may be fused together.

[0114] As used herein, C2-C 60 The alkylheteroaryl group has at least one C1 -C 60 C1-C substituted with alkyl groups 60 It means a heteroaryl group. As used herein, C6-C 60 The aryloxy group is -OA. 102 (where A 10 2 is C6-C 60 aryl group), and C6-C 60 The arylthio group is -SA 103 (where A 103 is C6-C 60 aryl group). As used herein, a monovalent non-aromatic fused polycyclic group refers to a group in which two or more rings are fused together, It contains only carbon atoms as ring atoms and the entire molecule is non-aromatic ty) (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic fused polycyclic group include a fluorenyl group. In this specification, the divalent non-aromatic fused polycyclic group has the same structure as the monovalent non-aromatic fused polycyclic group. means a divalent group having

[0115] As used herein, a monovalent non-aromatic hetero-fused polycyclic group refers to a group in which two or more rings are fused together. The ring atoms other than carbon are selected from N, O, P, Si, S, Ge, Se, and B. a monovalent group (e.g., 1 to 6) containing a heteroatom selected from the group consisting of aryl, ... 0 carbon atoms). Examples of the monovalent non-aromatic hetero-fused polycyclic group include a carbazolyl group. In this specification, the divalent non-aromatic condensed heteropolycyclic group refers to a monovalent non-aromatic condensed heteropolycyclic group. means a divalent group having the same structure as

[0116] As used herein, substituted C5-C 30 Carbocyclic groups, substituted C2-C 30 Hetero Ring groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C 3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl Groups, substituted C6-C 60 Aryl groups, substituted C7-C 60 alkylaryl groups, Substituted C6-C 60Aryloxy groups, substituted C6-C 60 arylthio group, Replaced C1-C 60 Heteroaryl groups, substituted C2-C 60 Alkylheteroary a substituted monovalent non-aromatic fused polycyclic group, and a substituted monovalent non-aromatic fused heteropolycyclic group; The substituents of a group are, independently of one another, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkini C1-C 60 alkoxy groups, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3 -C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 a Aryl group, C7-C 60 Alkylaryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, C2-C 60 Alkylheteroary monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )( Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q1 5), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 ) (Q 19 ), or any combination thereof, C1-C 60 Alkyl group, C2 -C 60 Alkenyl groups, C2-C 60 Alkynyl group, or C1-C 60 alkoxy groups, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 , -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkini group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Hetero Cycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkane Nyl group, C6-C 60 Aryl groups, C7-C 60 Alkylaryl groups, C6-C 60 Ants C6-C 60 Arylthio groups, C1-C 60Heteroaryl groups, C2-C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heterocyclic polycyclic group group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or any combination thereof, substituted or not substituted. Conversion, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Ally group, C7-C 60 Alkylaryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, C2-C 60 Alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group, -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ),or It can be any combination thereof.

[0117] In this specification, Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q3 9 independently represents hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, A cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a group thereof Salt, sulfonic acid group or its salt, phosphate group or its salt, deuterium, C1-C 60 alkyl groups, C6-C 60 aryl groups, or any combination thereof, substituted or unsubstituted C1- C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C6 0 alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups , C3-C 10 Cycloalkenyl groups, C1-C 10 heterocycloalkenyl group, deuterium, C1-C 60 Alkyl groups, C6-C 60 aryl groups, or any combination thereof; Substituted or unsubstituted C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent a fused heterocyclic non-aromatic ring group.

[0118] For example, in this specification, Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q3 1~Q 39 are independent of each other, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, - CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCD H2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2, or Ruiha Deuterium, C1-C 10 substituted with alkyl groups, phenyl groups, or any combination thereof or unsubstituted n-propyl, isopropyl, n-butyl, or sec-butyl group , isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group pentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group The alkyl group may be a phenyl group, a biphenyl group, or a naphthyl group. As used herein, "deuterated C1-C 60 Alkyl groups (or deuterated C1-C 20 Alkyl groups, deuterated C2-C 20 "Alkyl groups, etc." means groups with at least one deuterium atom. Substituted C1-C 60 Alkyl group (or C1- substituted with at least one deuterium) C 20 Alkyl groups, C2-C substituted with at least one deuterium 20 alkyl groups, etc.) means. For example, a "deuterated C1 alkyl group (i.e., a deuterated methyl group)" is - Includes -CD3, -CD2H and -CDH2. As used herein, "deuterated C3-C 10"Cycloalkyl group" means a group having at least one Deuterium-substituted C3-C 10 It means a cycloalkyl group. "Deuterated C3-C 10 Examples of the "cycloalkyl group" include the group represented by the above-mentioned chemical formula 10- 501, etc. can be referred to.

[0119] As used herein, "fluorinated C1-C 60 Alkyl group (or fluorinated C1-C 20 Al alkyl groups), fluorinated C3-C 10 Cycloalkyl groups and fluorinated C1-C 10 F Each "heterocycloalkyl group" is substituted with at least one fluoro group (-F). , C1-C 60 Alkyl group (or C1-C 20 alkyl groups, etc.), C3-C 10 Cyclo Alkyl groups and C1-C 10 It means a heterocycloalkyl group. For example, a "fluorinated C1 alkyl group (i.e., a fluorinated methyl group)" is -CF 3, including -CF2H and -CFH2. "Fluoride C1-C 60 Alkyl group (or fluorinated C1-C 20 alkyl groups, etc.)," C3-C Fluoride 10 Cycloalkyl group" or "Fluorinated C1-C 10 Heterocycloalkyl "Moto" is i) Fully fluorinated, where all hydrogen atoms in each group are replaced with fluoro groups. C1-C 60 Alkyl group (or fully fluorinated C1-C 20 alkyl groups, etc.), fully fluorinated C3-C 10 Cycloalkyl groups or fully fluorinated C1-C 10 Heterocycloalkyl groups There is, or ii) Partial hydrogen atoms in which not all hydrogen atoms in each group are replaced with fluoro groups ially) Fluoride C1-C 60 Alkyl group (or partially fluorinated C1-C 20 Alkyl group etc.), partially fluorinated C3-C 10 Cycloalkyl or partially fluorinated C1-C 10 Heterogeneity It may be a cycloalkyl group.

[0120] As used herein, "(C1-C 20 (Alkyl) "X" group means at least one C 1-C 20 Depicts an "X" group substituted with an alkyl group. For example, in this specification, "(C1-C 20 Alkyl)C3-C 10 cycloalkyl "group" means at least one C1-C 20 C3-C substituted with alkyl groups 10 Cycloa represents an alkyl group, and "(C1-C 20 "(alkyl)phenyl group" means a group having at least one C1 -C 20 This represents a phenyl group substituted with an alkyl group. An example of a (C1 alkyl)phenyl group is a toluyl group. . As used herein, "azaindole group, azabenzoborole group, azabenzophospho azaindene group, azabenzosilole group, azabenzogermol group, azabenzothiazole group, phene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilane group rol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoseleno Phen group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H -fluoren-9-one group, and azadibenzothiophene 5,5-dioxide group, respectively. Indole group, benzoborole group, benzophosphole group, indene group, benzosiloxane group, benzothiazolinone, benzogermol, benzothiophene, benzoselenophene, benzofurazolinone, dibenzoborane group, dibenzophosphole group, fluorene group, dibenzoborane group, Benzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9- It has the same backbone as the dibenzothiophene 5,5-dioxide group, but It means a heterocycle in which at least one of the carbon atoms forming the ring is replaced with nitrogen.

[0121] The following describes the compounds and organic light-emitting devices according to one embodiment of the present invention, with reference to synthesis examples and examples. The device will be described in more detail, but the present invention is not limited to the following synthesis examples and examples. It is not something that can be done. In the synthesis example below, the expression "Instead of "A", "B" was used" The amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0122] <<Compound synthesis examples>> <Synthesis example 1 (compound 1)> [ka]

[0123] [Synthesis of intermediate L1-3] 1.9 g (7.2 mmol) of 2-chloro-4-iodonicotinaldehyde was dissolved in acetonitrile. Mix with 60 ml of dichloromethane and 15 ml of water and add 0.4 g of PdCl2(PPh3)2 (0. 5 mmol), 3-fluorophenylboronic acid 1.0 g (7.2 mmol) and KC After adding O3 (2.5 g (18.0 mmol)), the mixture was heated to reflux at 85° C. for 16 hours. The resulting solution was concentrated under reduced pressure, and the organic layer was extracted with dichloromethane and water. The layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography. As a result, intermediate L1-3 (1.5 g (yield 87%)) was obtained. LC-MS m / z=236(M+H) +

[0124] [Synthesis of Intermediate L1-2] (Methoxymethyl)triphenylphosphonium chloride 5.4g (15.8mmol) was mixed with 50 ml of anhydrous ether, and then 1 ml of 1.0 M potassium tert-butoxide solution was added. 6 ml of the solution was added dropwise and stirred at room temperature for about 1 hour. Then, the intermediate L1-3 (1 0.5g (6.3mmol)) was slowly added dropwise and stirred at room temperature for 18 hours. The resulting mixture was extracted with water and ethyl acetate, and the organic layer was dissolved in mag- nesium sulfate. After drying with sodium hydroxide, the mixture was distilled under reduced pressure and purified by liquid chromatography to obtain intermediate L1. -2 (1.6 g (yield 96%)) was obtained. LC-MS m / z=264(M+H) +

[0125] [Synthesis of Intermediate L1-1] Intermediate L1-2 (1.4 g (5.1 mmol)) was mixed with 40 ml of dichloromethane. After slowly adding dropwise 3.0 ml of methanesulfonic acid, the mixture was stirred at room temperature for about 18 hours. The organic layer was extracted by adding saturated aqueous sodium bicarbonate solution to the resulting product. After drying with magnesium sulfate, the mixture was distilled under reduced pressure and purified by liquid chromatography. Intermediate L1-1 (1.0 g (yield 85%)) was obtained. LC-MS m / z=232(M+H) +

[0126] [Synthesis of intermediate L1] Intermediate L1-1 (1.0 g (4.1 mmol)) was dissolved in tetrahydrofuran (THF) 0.9 g (6.2 mL) of 3,5-dimethylphenylboronic acid was mixed with 10 mL of water. mmol), Pd(OAc)2(0.09g(0.4mmol)), Sphos(0.3 5g (0.82mmol)) and K2CO3 (1.4g (10.3mmol)) were added. Then, the mixture was heated under reflux for one day. The resulting product was extracted with ethyl acetate and water, and the organic layer was extracted with magnesium sulfate. After drying over sodium, the mixture was distilled under reduced pressure and purified by liquid chromatography to give intermediate L1( 1.1 g (yield 85%) was obtained. LC-MS m / z=302(M+H) +

[0127] [Synthesis of Intermediate L1 Dimer] Intermediate L1 (1.05 g (3.4 mmol)) and iridium chloride 0.6 g (1.6 mm ol) was mixed with 40 mL of ethoxyethanol and 15 mL of distilled water, and then 2 The mixture was heated to reflux for 4 hours. The temperature of the resultant is then lowered to room temperature, and the resulting solid is filtered. The solid was thoroughly washed with water / methanol / hexane in that order and dried in a vacuum oven. This gave intermediate L1Dimer (1.1 g).

[0128] [Synthesis of Compound 1] Intermediate L1Dimer (1.0 g (0.63 mmol)), 3,7-diethylnonane- 4,6-dione (4.5 mmol) and Na2CO3 (0.48 g (4.5 mmol)) and 40 mL of ethoxyethanol were mixed and stirred at 90°C for 24 hours. The temperature of the resulting product is lowered to room temperature, and the solids formed are filtered out. The product was purified by chromatography to give Compound 1 (0.6 g, 47% yield). LC-MS m / z=1007(M+H) +

[0129] <Synthesis example 2 (compound 2)> [ka]

[0130] [Synthesis of intermediate L2-5] Dichloromethyl methyl ether 15g (130mmol) and dichloromethane 200ml After mixing, SnCl4 (15 ml (130 mmol)) was added slowly at 0°C, and the The mixture was stirred for 2 hours. 16.5 g of 1-fluoro-7-methylnaphthalene mixed with 100 ml of CH2Cl2 (103 mmol) was slowly added dropwise, and the mixture was stirred at room temperature for about 16 hours. After the reaction was completed, the reaction mixture was poured into 150 ml of ice water and the extracted organic layer was separated with mag- nesium sulfate. After drying over sodium and distilling under reduced pressure, the product was purified by liquid chromatography to give intermediate L2-5. (12.2 g (yield 63%)) was obtained. LC-MS m / z=189(M+H) +

[0131] [Synthesis of intermediate L2-4] Intermediate L2-5 (10 g (53.1 mmol)), malonic acid 6.7 g (64.2 mmol) l) and 6.3 ml (64.2 mmol) of piperidine were mixed with 80 ml of pyridine. Thereafter, the mixture was stirred at 90°C for about 18 hours. After the reaction was completed, pyridine was distilled off under reduced pressure, and water was added dropwise to the reaction mixture. The resulting product was acidified to a pH of about 4 with 4N HCl. The resulting solid was filtered and washed several times with hexane. The compound obtained therefrom was dried without any purification process to give intermediate L2-4 (11 g (yield 75%)). LC-MS m / z=231(M+H) +

[0132] [Synthesis of intermediate L2-3] Intermediate L2-4 (11 g (47.8 mmol)) was mixed with 250 ml of dry acetone. After that, 5.5 ml (57.4 mmol) of ethyl chloroformate was added at room temperature, and triethylamine was added. 17 ml (119.5 mmol) of ethanol was slowly added dropwise. The reaction mixture was stirred at room temperature for 2 hours, and then the sodium azide was mixed with 100 ml of water at 0°C. 6.2 g (95.6 mmol) of sodium was slowly added dropwise to the mixture, and the mixture was stirred for about 1 hour. After the reaction is completed, the reaction mixture is poured into ice water and stirred, and the resulting solid is filtered. Intermediate L2-3 (11 g, 90% yield) was obtained without further purification.

[0133] [Synthesis of intermediate L2-2] 56 ml of tributylamine was mixed with 170 ml of diphenyl ether, and then The intermediate agent L2-3 (5 g (19.6 mmol)) mixed with 170 ml of diethyl ether was gradually added. The mixture was heated and stirred for about 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and then 300 ml of hexane was added and stirred at room temperature for about 1 hour. The solid formed at this time was filtered and obtained as intermediate L2-2 (2.4 g, yield) without further purification. 55%)). LC-MS m / z=228(M+H) +

[0134] [Synthesis of intermediate L2-1] Intermediate L2-2 (2.4 g (10.6 mmol)) was dissolved in 380 ml of POCl. The mixture was heated and stirred for about 18 hours. After the reaction is complete, the mixture is cooled and slowly added dropwise to 200 ml of ice water. It was neutralized with an aqueous solution. The organic layer extracted with dichloromethane was dried over magnesium sulfate and then evaporated under reduced pressure. After collecting the residue, the mixture was purified by liquid chromatography to give intermediate L2-1 (2.0 g (yield 80%)). obtained. LC-MS m / z=246(M+H) +

[0135] [Synthesis of intermediate L2] The same procedure as in Synthesis Example 1 was repeated except that intermediate L2-1 was used instead of intermediate L1-1. Intermediate L2 (1.8 g, 73% yield) was obtained using the same method as that for intermediate L1. Got it. LC-MS m / z=316(M+H) +

[0136] [Synthesis of intermediate L2Dimer] The same intermediate as in Synthesis Example 1, except that intermediate L2 was used instead of intermediate L1. The intermediate L2Dimer was obtained using the same method as for synthesizing L1Dimer.

[0137] [Synthesis of Compound 2] Except that instead of the intermediate L1Dimer, the intermediate L2Dimer was used. Compound 2 (0.6 g, yield 40%) was synthesized using the same method as that of Compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1035(M+H) +

[0138] <Synthesis example 3 (compound 3)> [ka]

[0139] [Synthesis of intermediate L3] Intermediate L1 (2.0 g (6.6 mmol)) and 80 mL of anhydrous tetrahydrofuran (THF) After mixing with 4.6 ml of 1.6 M BuLi solution ( 7.3 mmol) was slowly added. After about 2 hours, 1.3 ml (9.9 mmol) of chlorotriphenylsilane was slowly added dropwise. The mixture was stirred at room temperature for 18 hours. After the reaction was completed, the mixture was extracted with 60 ml of ethyl acetate and water. The obtained organic layer was The mixture was dried over ice and distilled under reduced pressure. The residue was purified by liquid chromatography to give intermediate L3 (1.1 g (yield 45%)). LC-MS m / z=374(M+H) +

[0140] [Synthesis of intermediate L3Dimer] The same procedure as in Synthesis Example 1 except that intermediate L3 was used instead of intermediate L1. The intermediate L3Dimer was obtained using the same method as for synthesizing L1Dimer.

[0141] [Synthesis of Compound 3] Except that instead of the intermediate L1Dimer, the intermediate L3Dimer was used. Compound 3 (0.7 g, yield 45%) was synthesized using the same method as that for compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1151(M+H) +

[0142] <Synthesis example 4 (compound 4)> [ka]

[0143] [Synthesis of intermediate L4-6] Instead of 3-fluorophenylboronic acid, (3-bromo-5-(trifluoromethyl) Synthesis of Intermediate L1-3 in Synthesis Example 1, except that phenyl)boronic acid was used. The same procedure was used to obtain intermediate L4-6 (6.2 g (71% yield)). LC-MS m / z=364(M+H) +

[0144] [Synthesis of intermediate L4-5] The same procedure as in Synthesis Example 1 was repeated except that intermediate L4-6 was used instead of intermediate L1-3. Intermediate L4-5 (6.5 g, yield 98%) was synthesized using the same method as that used for synthesizing intermediate L1-2. %) was obtained. LC-MS m / z=392(M+H) +

[0145] [Synthesis of intermediate L4-4] The same procedure as in Synthesis Example 1 was repeated, except that intermediate L4-5 was used instead of intermediate L1-2. Intermediate L4-4 (2.1 g, yield 35%) was synthesized using the same method as that used for synthesizing intermediate L1-1. %) was obtained. LC-MS m / z=360(M+H) +

[0146] [Synthesis of intermediate L4-3] Intermediate L4-4 (2.1 g (5.9 mmol)) was mixed with 120 ml of acetonitrile. After that, 1.1 ml (8.9 mmol) of chlorotrimethylsilane and 1.3 g (8 0.9 mmol)) was added and heated to reflux at 90°C for 36 hours. After the reaction was completed, the obtained active compound was extracted with 60 ml of ethyl acetate and saturated aqueous sodium sulfate solution. The organic layer was dried over magnesium sulfate and distilled under reduced pressure. The mixture was purified by liquid chromatography to give intermediate L4-3 (2.3 g, yield 87%). LC-MS m / z=452(M+H) +

[0147] [Synthesis of intermediate L4-2] The same procedure as in Synthesis Example 1 was repeated, except that intermediate L4-3 was used instead of intermediate L1-1. Using the same method as that for intermediate L1, intermediate L4-2 (1.8 g, 80% yield) was obtained. ) was obtained. LC-MS m / z=430(M+H) +

[0148] [Synthesis of intermediate L4-1] Intermediate L4-2 (1.8 g (4.2 mmol)) was dissolved in tetrahydrofuran (THF) 6 Mix 0 ml of 4,4,5,5-tetramethyl-2-(prop-1-ene) with 15 ml of water. 0.9 g (5.0 mmol) of phenyl-2-yl-1,3,2-dioxaborolane and Pd( OAc)2(0.1g(0.4mmol)), Sphos(0.3g(0.8mmol) ), K2CO3 (1.5 g (10.5 mmol)), and heated to reflux at 80°C for 18 hours. made him do so. After the reaction was completed, the reaction mixture was extracted with 50 ml of ethyl acetate. The obtained organic layer was After drying over sodium and distilling under reduced pressure, the product was purified by liquid chromatography to give intermediate L4- 1.2 g (75% yield) of 1 was obtained. LC-MS m / z=392(M+H) +

[0149] [Synthesis of intermediate L4] Intermediate L4-1 (1.2 g (3.1 mmol)) was mixed with 60 ml of ethyl alcohol. After adding Pd / C (0.1 g (10 wt%)), hydrogen was injected and the mixture was stirred at room temperature for 18 hours. After the reaction was completed, the reaction mixture was passed through a Celite pad, concentrated under reduced pressure, and then The residue was purified by liquid chromatography to give intermediate L4 (1.1 g (yield 90%)). LC-MS m / z=394(M+H) +

[0150] [Synthesis of intermediate L4Dimer] The same intermediate as in Synthesis Example 1, except that intermediate L4 was used instead of intermediate L1. The intermediate L4Dimer was obtained using the same method as for synthesizing L1Dimer.

[0151] [Synthesis of Compound 4] Except that instead of the intermediate L1Dimer, the intermediate L4Dimer was used. Compound 4 (0.6 g, yield 38%) was obtained using the same method as that used to synthesize Compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1191(M+H) +

[0152] <Synthesis example 5 (compound 5)> [ka]

[0153] [Synthesis of intermediate L5-3] Instead of 3-fluorophenylboronic acid, 4-(trifluoromethyl)phenylboronic acid The same method as that for intermediate L1-3 in Synthesis Example 1 was used, except that carboxylic acid was used instead. This was used to obtain intermediate L5-3 (2.2 g, 75% yield). LC-MS m / z=286(M+H) +

[0154] [Synthesis of intermediate L5-2] The same procedure as in Synthesis Example 1 was repeated except that intermediate L5-3 was used instead of intermediate L1-3. Intermediate L5-2 (2.4 g, yield: 9%) was obtained using the same method as in the synthesis of intermediate L1-2. 9%)). LC-MS m / z=314(M+H) +

[0155] [Synthesis of intermediate L5-1] Instead of intermediate L1-2, intermediate L5-2 was used, and instead of methanesulfonic acid, The same procedure as in Synthesis Example 1, except that trifluoromethanesulfonic acid was used. The same synthesis method as for 1 was used to obtain intermediate L5-1 (1.0 g, 50% yield). LC-MS m / z=282(M+H) +

[0156] [Synthesis of intermediate L5] The same procedure as in Synthesis Example 1 was repeated except that intermediate L5-1 was used instead of intermediate L1-1. Intermediate L5 (0.8 g, 70% yield) was synthesized using the same method as that for intermediate L1. Got it. LC-MS m / z=352(M+H) +

[0157] [Synthesis of intermediate L5Dimer] The same intermediate as in Synthesis Example 1, except that intermediate L5 was used instead of intermediate L1. The intermediate L5Dimer was obtained using the same method as for synthesizing L1Dimer.

[0158] [Synthesis of Compound 5] Except that instead of the intermediate L1Dimer, the intermediate L5Dimer was used. Compound 5 (0.3 g, yield 40%) was obtained using the same synthesis method as that of Compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1107(M+H) +

[0159] <Synthesis example 6 (compound 6)> [ka]

[0160] [Synthesis of intermediate L6-2] 6.0 g (23.7 mmol) of 2-chloro-4-iodo-3-methylpyridine was added to acetonitrile. Mix with 80 ml of nitrile and 20 ml of water. PdCl2(PPh3)2 (1.2 g 1.6mmol)), 2-fluoro-6-(4,4,5,5-tetramethyl-1,3,2 -Dioxaborolan-2-yl)-3-(trimethylsilyl)benzaldehyde 8.4g (26.1 mmol) and K2CO3 (8.2 g (59.2 mmol)) were added, and then 8 The mixture was heated to reflux at 5°C for 18 hours. The resulting product was concentrated under reduced pressure, and the organic layer was extracted with ethyl acetate and water. After drying with magnesium sulfate, the mixture was distilled under reduced pressure and purified by liquid chromatography to obtain the intermediate L6-2 (6.1 g (yield 80%)) was obtained. 2-Fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane In the case of (-2-yl)-3-(trimethylsilyl)benzaldehyde, the reaction is as shown above. obtained by. LC-MS m / z=322(M+H) +

[0161] [Synthesis of intermediate L6-1] The same procedure as in Synthesis Example 1 was repeated, except that intermediate L6-2 was used instead of intermediate L1-2. Intermediate L6-1 (1.7 g, yield 30%) was synthesized using the same method as that used for synthesizing intermediate L1-1. %) was obtained. LC-MS m / z=304(M+H) +

[0162] [Synthesis of intermediate L6] The same procedure as in Synthesis Example 1 was repeated except that intermediate L6-1 was used instead of intermediate L1-1. Intermediate L6 (1.5 g, 73% yield) was obtained using the same method as that for intermediate L1. Got it. LC-MS m / z=374(M+H) +

[0163] [Synthesis of intermediate L6Dimer] The same intermediate as in Synthesis Example 1, except that intermediate L6 was used instead of intermediate L1. The intermediate L6Dimer was obtained using the same method as for synthesizing L1Dimer.

[0164] [Synthesis of Compound 6] Except that instead of the intermediate L1Dimer, the intermediate L6Dimer was used. Compound 6 (0.8 g, yield 30%) was obtained using the same method as that used to synthesize Compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1180(M+H) +

[0165] <Synthesis example 7 (compound 7)> [ka]

[0166] [Synthesis of intermediate L7-1] Instead of 3,5-dimethylphenylboronic acid, 2-(3-(tert-butyl)-5 -methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane The same method as for the synthesis of intermediate L1 in Synthesis Example 1 was used, except that Interstitial body L7-1 was obtained. LC-MS m / z=344(M+H)+

[0167] [Synthesis of intermediate L7] The same procedure as in Synthesis Example 3 was repeated except that intermediate L7-1 was used instead of intermediate L1. Intermediate L7 (0.9 g, 50% yield) was obtained using the same method as for the synthesis of intermediate L3. . LC-MS m / z=416(M+H) +

[0168] [Synthesis of Intermediate L7 Dimer] The same intermediate as in Synthesis Example 1, except that intermediate L7 was used instead of intermediate L1. The intermediate L7Dimer was obtained using the same method as for synthesizing L1Dimer.

[0169] [Synthesis of Compound 7] Except that instead of intermediate L1Dimer, intermediate L7Dimer was used. Compound 7 (0.3 g, yield 35%) was synthesized using the same method as that of Compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1235(M+H) +

[0170] <Synthesis example 8 (compound 8)> [ka]

[0171] [Synthesis of intermediate L8] The point that chlorotrimethylgermane was used instead of chlorotrimethylsilane Intermediate L8 (1.1 g) was obtained by the same method as that for intermediate L3 in Synthesis Example 3, except for the following: (yield 40%) was obtained. LC-MS m / z=420(M+H )+

[0172] [Synthesis of intermediate L8Dimer] The same intermediate as in Synthesis Example 1, except that intermediate L8 was used instead of intermediate L1. The intermediate L8Dimer was obtained using the same method as for synthesizing L1Dimer.

[0173] [Synthesis of Compound 8] Except that instead of intermediate L1Dimer, intermediate L8Dimer was used. Compound 8 (0.5 g, yield 46%) was synthesized using the same method as that for compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1243(M+H) +

[0174] <Synthesis example 9 (compound 9)> [ka]

[0175] [Synthesis of intermediate L9-5] 15g (64mmol) of 4-bromo-1-naphthaldehyde in 100ml of chloroform Mix with 10 ml (96 mmol) of aminoacetaldehyde dimethyl acetal Slowly add hot and stir. After 1 hour, the mixture was heated to 100°C, the solvent was removed, and the resulting reaction mixture was cooled to room temperature. Then, without further purification, intermediate L9-5 (20 g, yield 99%) was obtained. LC-MS m / z=322(M+H) +

[0176] [Synthesis of intermediate L9-4] Intermediate L9-5 (20 g (62 mmol)) was mixed with 100 ml of chloroform. 6 ml (62 mmol) of chloroformate, 9 ml (74 mmol) of trimethyl phosphite, ol) was slowly added dropwise in order. The resulting reaction mixture was stirred at room temperature for about 48 hours and then added with 1.0M (TiCl4(2 50 ml (250 mmol))) was slowly added dropwise at 0°C, and the mixture was heated under reflux for about 48 hours. . After the reaction was completed, the reaction mixture was cooled to room temperature and then poured into ice water. The aqueous layer was washed with dichloromethane and then added to an aqueous solution of 140 g (495 mmol) of tartrate. The organic layer obtained by neutralizing with saturated aqueous NaHCO3 solution and extracting with dichloromethane The product was purified by liquid chromatography to give intermediate L9-4 (5.4 g (yield 34%)). . LC-MS m / z=258(M+H) +

[0177] [Synthesis of intermediate L9-3] Intermediate L9-4 (5 g (19 mmol)) was mixed with 60 ml of dichloromethane, 6.7 g (38 mmol) of metachloroperbenzoic acid (mCPBA) was added dropwise at 0°C. The reaction mixture was stirred at room temperature for about 18 hours, and then extracted with a 6N-KOH aqueous solution. The organic layer was dried over magnesium sulfate and then obtained intermediate L9-3 (5. 1 g (yield 99%) was obtained.

[0178] [Synthesis of intermediate L9-2] 35 g (18 mmol) of intermediate L9 was mixed with 60 ml of dichloromethane, and then PO Br3 (6.5 g (22 mmol)) was slowly added dropwise at 0°C, and then dimethylformamide was added. 0.8 ml (9 mmol) of dichloromethane (DMF) was slowly added, and the mixture was stirred at room temperature for about 18 hours. After the reaction was completed, the organic layer obtained after neutralization with saturated aqueous NaHCO3 was After drying over sodium hydroxide, the mixture was purified by liquid chromatography to give intermediate L9-2 (2.2 g The compound was obtained in a 30% yield. LC-MS m / z=336(M+H) +

[0179] [Synthesis of intermediate L9-1] The same procedure as in Synthesis Example 1 was repeated, except that intermediate L9-2 was used instead of intermediate L1-1. Using the same method as that for synthesizing intermediate L1, intermediate L9-1 (1.6 g, 75% yield) was obtained. ) was obtained. LC-MS m / z=362(M+H) +

[0180] [Synthesis of intermediate L9] Intermediate L9-1 (1.5 g (4.1 mmol)) was dissolved in tetrahydrofuran (THF) After mixing with 0 ml of Pd(PPh3)4 (0.3 g (0.3 mmol)), (4-furan 0.7 g (4.9 mmol) fluorophenyl)boronic acid, 1.4 g (10. 2 mmol)) and 10 ml of water were added, and the mixture was heated to reflux at 80°C for about 18 hours. After the reaction was completed, the organic layer obtained by extraction with ethyl acetate was dried over magnesium sulfate. Thereafter, the mixture was purified by liquid chromatography to obtain intermediate L9 (1.2 g (yield 82%)). LC-MS m / z=378(M+H) +

[0181] [Synthesis of intermediate L9Dimer] The same procedure as in Synthesis Example 1 except that intermediate L9 was used instead of intermediate L1. The intermediate L9Dimer was obtained using the same method as for synthesizing L1Dimer.

[0182] [Synthesis of Compound 9] Except that instead of intermediate L1Dimer, intermediate L9Dimer was used. Compound 9 (0.7 g, yield 47%) was obtained using the same method as that used to synthesize Compound 1 in Synthesis Example 1. %) was obtained. LC-MS m / z=1159(M+H) +

[0183] <Synthesis example 10 (compound 10)> [ka]

[0184] [Synthesis of intermediate L10-3] 6.0 g (23.7 mmol) of 2-chloro-4-iodo-3-methylpyridine was added to acetonitrile. Mix with 80 ml of nitrile and 20 ml of water. PdCl2(PPh3)2 (1.2 g 1.6 mmol), 3-fluoro-2-formylphenylboronic acid 4.4 g (26.1 After adding K2CO3 (8.2 g (59.2 mmol)) and K2CO3 (8.2 g (59.2 mmol)), the mixture was heated at 80 °C for 18 h. The mixture was heated to reflux for 1 hour. The resulting product was concentrated under reduced pressure, and the organic layer was extracted with ethyl acetate and water. After drying with magnesium sulfate, the mixture was distilled under reduced pressure and purified by liquid chromatography. Intermediate L10-3 (5.0 g (yield 85%)) was obtained. LC-MS m / z=250(M+H) +

[0185] [Synthesis of intermediate L10-2] Intermediate L10-3 (4.0 g (16.0 mmol)) was dissolved in anhydrous N,N-dimethylformamide. Dissolve in 150 ml of ethanol and slowly add 1.0 M potassium hydroxide in tetrahydrofuran (THF) at room temperature. After slowly adding 19 ml (19.2 mmol) of sodium tert-butoxide solution, Heated at 0°C for 6 hours. After the reaction was completed, the organic layer obtained by extraction with ethyl acetate and water was dried over magnesium sulfate. made him do so. The reaction mixture was filtered, concentrated under reduced pressure, and purified by liquid chromatography to give intermediate L10 -2 (1.3 g (yield 35%)) was obtained. LC-MS m / z=232(M+H) +

[0186] [Synthesis of Intermediate L10-1] The same procedure as in Synthesis Example 1 was repeated except that intermediate L10-2 was used instead of intermediate L1-1. Intermediate L10-1 (1.2 g, yield 70%) was synthesized using the same method as that used for synthesis of intermediate L1 in Example 1. %) was obtained. LC-MS m / z=302(M+H) +

[0187] [Synthesis of intermediate L10] Instead of chlorotrimethylsilane, chlorodimethylphenylsilane was used. Intermediate L10 (0 0.8g (yield 46%) was obtained. LC-MS m / z=436(M+H) +

[0188] [Synthesis of intermediate L10Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L10 was used instead of Intermediate L1. The intermediate L10Dimer was obtained using the same method as for the synthesis of the L1Dimer.

[0189] [Synthesis of Compound 10] Except that intermediate L10Dimer was used instead of intermediate L1Dimer. Compound 10 (0.35 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. The result was a 42% success rate. LC-MS m / z=1276(M+H) +

[0190] <Synthesis example 11 (compound 11)> [ka]

[0191] [Synthesis of intermediate L11-5] 5.0 g (32.0 mmol) of 1-naphthaldehyde was dissolved in 60 ml of anisole. Then, Pd(PPh3)4 (2.6 g (2.24 mmol)), bis[2-(diphenylphosphine Sphinophenyl] ether (DPEPhos) 1.7g (3.2mmol), K3P O4 (11 g (80 mmol)), 1,1,1-Trifluoro-2-iodoethane After adding 10.6 ml (64 mmol) of e and 20 ml of water, the mixture was heated at 130°C for 24 hours. Ta. After the reaction was completed, the mixture was neutralized with 1N-HCl and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The reaction mixture obtained therefrom was distilled under reduced pressure, and then purified by liquid chromatography to obtain an intermediate. Compound L11-5 (3.9 g, yield 52%) was obtained. LC-MS m / z=239(M+H) +

[0192] [Synthesis of intermediate L11-4] The use of intermediate L11-5 instead of 4-bromo-1-naphthaldehyde Intermediate L11- was synthesized by the same method as that for intermediate L9-5 in Synthesis Example 9, except for the following: 4 (3.8 g (73% yield)) was obtained. LC-MS m / z=326(M+H) +

[0193] [Synthesis of intermediate L11-3] The same procedure as in Synthesis Example 1 was repeated except that intermediate L11-4 was used instead of intermediate L9-5. Intermediate L11-3 (0.9 g, yield) was synthesized using the same method as that used for synthesizing intermediate L9-4 in Example 9. 28%)). LC-MS m / z=262(M+H) +

[0194] [Synthesis of intermediate L11-2] The same procedure as in Synthesis Example 1 was repeated except that intermediate L11-3 was used instead of intermediate L9-4. Intermediate L11-2 (0.9 g, yield) was obtained using the same method as that used for synthesizing intermediate L9-3 in Example 9. 99%)).

[0195] [Synthesis of intermediate L11-1] The same procedure as in Synthesis Example 1 was repeated except that intermediate L11-2 was used instead of intermediate L9-3. Intermediate L11-1 (0.7 g, yield) was obtained using the same method as that used for synthesizing intermediate L9-3 in Example 9. 63%)). LC-MS m / z=341(M+H) +

[0196] [Synthesis of intermediate L11] The same procedure as in Synthesis Example 1 was repeated except that intermediate L11-1 was used instead of intermediate L1-1. Intermediate L11 (0.6 g, 85% yield) was obtained using the same method as that for intermediate L1 in Example 1. ) was obtained. LC-MS m / z=366(M+H) +

[0197] [Synthesis of intermediate L11Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L11 was used instead of Intermediate L1. The intermediate L11Dimer was obtained using the same method as that for the synthesis of L1Dimer.

[0198] [Synthesis of Compound 11] Except that the intermediate L11Dimer was used instead of the intermediate L1Dimer. Compound 11 (0.25 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. The result was a 40% success rate. LC-MS m / z=1135(M+H) +

[0199] <Synthesis example 12 (compound 12)> [ka]

[0200] [Synthesis of intermediate L12-1] The same procedure was followed except that iodine was used instead of chlorodimethylphenylsilane. Intermediate L12-1 (1.4 g) was synthesized using the same method as that for synthesizing intermediate L10 in Example 10. The compound was obtained in a 50% yield. LC-MS m / z=428(M+H) +

[0201] [Synthesis of intermediate L12] Intermediate L12-1 (1.2 g (2.8 mmol)) was dissolved in tetrahydrofuran (THF) 0 ml of phenylboronic acid and 10 ml of water were mixed, and 0.4 g (3.4 mmol) of Pd( PPh3)4(0.2g(0.2mmol)), K2CO3(1.0g(7.0mmol) )) was added, and the mixture was heated to reflux at 85°C for 18 hours. After the reaction was completed, the reaction mixture was extracted with 30 ml of ethyl acetate. The obtained organic layer was After drying over sodium and distilling under reduced pressure, the product was purified by liquid chromatography to give intermediate L12. (0.8 g (78% yield)) was obtained. LC-MS m / z=378(M+H) +

[0202] [Synthesis of intermediate L12Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L12 was used instead of Intermediate L1. The intermediate L12Dimer was obtained using the same method as for the synthesis of the L1Dimer.

[0203] [Synthesis of Compound 12] Except that intermediate L12Dimer was used instead of intermediate L1Dimer. Compound 12 (0.3 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. 40%)). LC-MS m / z=1159(M+H) +

[0204] <Synthesis example 13 (compound 13)> [ka]

[0205] [Synthesis of intermediate L13-4] 5.0 g (22.2 mmol) of 2-bromo-6-fluoronaphthalene was dissolved in anhydrous tetrahydrofuran. After dissolving in 60 ml of THF, the solution was diluted to 1.6 M in 15 ml of hexane at -78°C. -BuLi solution (24.4 mmol) was slowly added. After about 2 hours, 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-diox- 5.4 ml (26.6 mmol) of saborolane was slowly added dropwise, and the mixture was stirred at room temperature for 18 hours. After the reaction was completed, the organic layer was extracted with 30 ml of ethyl acetate and water. The mixture was dried over ice and distilled under reduced pressure. The mixture was purified by liquid chromatography to give intermediate L13-4 (5.1 g, 85% yield). . LC-MS m / z=273(M+H) +

[0206] [Synthesis of intermediate L13-3] Intermediate L13-4 (5.1 g (18.7 mmol)) was dissolved in 120 ml of acetonitrile and Mix with 30 ml of water and PdCl2(PPh3)2 (0.9 g (1.3 mmol)), 2-chloro-4-iodonicotinaldehyde 5.0 g (18.7 mmol) and KCO After adding 3 (6.5 g (46.8 mmol)), the mixture was heated to reflux at 80° C. for 24 hours. The resulting solution was concentrated under reduced pressure, and the organic layer was extracted with dichloromethane and water. The layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography. The intermediate L13-3 (4.4 g, yield 82%) was obtained. LC-MS m / z=286(M+H) +

[0207] [Synthesis of intermediate L13-2] (Methoxymethyl)triphenylphosphonium chloride 12.0 g (35.0 mmol) ) was mixed with 150 ml of anhydrous ether and then dissolved in 1.0 M potassium tert-butoxide. 35 ml of the solution was added dropwise, and the mixture was stirred at room temperature for about 2 hours. Then, intermediate L13-3( 4.0 g (14.0 mmol)) was slowly added dropwise, and the mixture was stirred at room temperature for 18 hours. The resulting mixture was extracted with water and ethyl acetate, and the organic layer was dissolved in mag- nesium sulfate. After drying with sodium, it was distilled under reduced pressure and purified by liquid chromatography to obtain intermediate L13-2. (4.2 g (yield 95%)) was obtained. LC-MS m / z=314(M+H) +

[0208] [Synthesis of intermediate L13-1] Intermediate L13-2 (4.0 g (12.7 mmol)) was mixed with 250 ml of chloroform. After adding 5.6 ml (63.5 mmol) of triflic acid dropwise, the mixture was heated at 60°C for about 4 hours. The mixture was stirred for a while. The organic layer was extracted by adding saturated aqueous sodium bicarbonate solution to the resulting product. After drying with magnesium sulfate, the mixture was distilled under reduced pressure and purified by liquid chromatography to obtain the intermediate L13-1 (1.0 g (yield 28%)) was obtained. LC-MS m / z=282(M+H) +

[0209] [Synthesis of intermediate L13] The same procedure as in Synthesis Example 1 was repeated except that intermediate L13-1 was used instead of intermediate L1-1. Intermediate L13 (1.0 g, 82% yield) was obtained using the same method as that for intermediate L1 in Example 1. ) was obtained. LC-MS m / z=352(M+H) +

[0210] [Synthesis of intermediate L13Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L13 was used instead of Intermediate L1. The intermediate L13Dimer was obtained using the same method as that for the synthesis of the L1Dimer.

[0211] [Synthesis of Compound 13] Except that intermediate L13Dimer was used instead of intermediate L1Dimer. Compound 13 (0.5 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. 46%)). LC-MS m / z=1107(M+H) +

[0212] <Synthesis example 14 (compound 14)> [ka]

[0213] [Synthesis of intermediate L14-5] 4.0 g (20.9 mmol) of 6-chloroisoquinoline-7-carbaldehyde was added to tetrachloroisoquinoline-7-carbaldehyde. Mix with 80 ml of trihydrofuran (THF) and 20 ml of water, and Pd(PPh3)4(1 0.6g (1.4mmol)), (3-fluoro-4-methylphenyl)boronic acid 3.9g (25.1 mmol) and K2CO3 (7.2 g (52.3 mmol)) were added, and then 1 The mixture was heated under reflux for 8 hours. The resulting product was concentrated under reduced pressure, dissolved in dichloromethane, and extracted with water. The organic layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography. As a result, intermediate L14-5 (4.4 g, 80% yield) was obtained. LC-MS m / z=266(M+H) +

[0214] [Synthesis of intermediate L14-4] The same procedure as in Synthesis Example 1 was repeated except that intermediate L14-5 was used instead of intermediate L1-3. Intermediate L14-4 (4.4 g, yield: 1.0%) was synthesized using the same method as that for intermediate L1-2 in Example 1. (95%)). LC-MS m / z=294(M+H) +

[0215] [Synthesis of intermediate L14-3] The synthesis was the same as above, except that intermediate L14-4 was used instead of intermediate L13-2. Intermediate L14-3 (1.9 g) was synthesized using the same method as in Example 13 for intermediate L13-1. (yield 52%) was obtained. LC-MS m / z=262(M+H) +

[0216] [Synthesis of intermediate L14-2] The same procedure as in Synthesis Example 1 was repeated except that intermediate L14-3 was used instead of intermediate L9-4. Intermediate L14-2 (0.9 g, yield) was synthesized using the same method as that used for synthesizing intermediate L9-3 in Example 9. 99%)).

[0217] [Synthesis of intermediate L14-1] The same procedure as in Synthesis Example 1 was repeated except that intermediate L14-2 was used instead of intermediate L9-3. Intermediate L14-1 (1.3 g, yield) was obtained using the same method as that used for synthesizing intermediate L9-2 in Example 9. 55%)). LC-MS m / z=341(M+H) +

[0218] [Synthesis of intermediate L14] The same procedure as in Synthesis Example 1 was repeated except that intermediate L14-1 was used instead of intermediate L1-1. Using the same method as that for synthesizing intermediate L1 in 1, intermediate L14 (1.1 g, 80% yield) was obtained. ) was obtained. LC-MS m / z=366(M+H) +

[0219] [Synthesis of intermediate L14Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L14 was used instead of Intermediate L1. The intermediate L14Dimer was obtained using the same method as that for the synthesis of the L1Dimer.

[0220] [Synthesis of Compound 14] Except that intermediate L14Dimer was used instead of intermediate L1Dimer. Compound 14 (0.6 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. 40%)). LC-MS m / z=1135(M+H) +

[0221] <Synthesis example 15 (compound 15)> [ka]

[0222] [Synthesis of intermediate L15-5] Instead of 6-chloroisoquinoline-7-carbaldehyde, 4-bromonicotinaldehyde The synthesis method was the same as that of intermediate L14-5 in Synthesis Example 14, except that hydride was used. Using this method, intermediate L15-5 (2.8 g, 85% yield) was obtained. LC-MS m / z=202(M+H) +

[0223] [Synthesis of intermediate L15-4] The same procedure as in Synthesis Example 1 was repeated except that intermediate L15-5 was used instead of intermediate L1-3. Intermediate L15-4 (3.0 g, yield) was obtained using the same method as that used to synthesize intermediate L1-2 in Example 1. (95%)). LC-MS m / z=230(M+H) +

[0224] [Synthesis of intermediate L15-3] The synthesis was the same as above, except that intermediate L15-4 was used instead of intermediate L13-2. Intermediate L15-3 (0.9 g) was synthesized using the same method as in Example 13 for intermediate L13-1. (yield 35%) was obtained. LC-MS m / z=198(M+H) +

[0225] [Synthesis of intermediate L15-2] The same procedure as in Synthesis Example 1 was repeated except that intermediate L15-3 was used instead of intermediate L9-4. Intermediate L15-2 (0.9 g, yield) was synthesized using the same method as that used for synthesizing intermediate L9-3 in Example 9. 99%)).

[0226] [Synthesis of intermediate L15-1] The same procedure as in Synthesis Example 1 was repeated except that intermediate L15-2 was used instead of intermediate L9-3. Intermediate L15-1 (0.8 g, yield) was synthesized using the same method as that used for synthesizing intermediate L9-2 in Example 9. 70%)). LC-MS m / z=276(M+H) +

[0227] [Synthesis of intermediate L15] The same procedure as in Synthesis Example 1 was repeated except that intermediate L15-1 was used instead of intermediate L1-1. Using the same method as that for intermediate L1 in Example 1, intermediate L15 (0.7 g, 85% yield) was obtained. ) was obtained. LC-MS m / z=302(M+H) +

[0228] [Synthesis of intermediate L15Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L15 was used instead of Intermediate L1. The intermediate L15Dimer was obtained using the same method as that for the synthesis of the L1Dimer.

[0229] [Synthesis of Compound 15] Except that intermediate L15Dimer was used instead of intermediate L1Dimer. Compound 15 (0.2 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. 40%)). LC-MS m / z=1035(M+H) +

[0230] <Synthesis example 16 (compound 16)> [ka]

[0231] [Synthesis of intermediate L16-3] Instead of (4-(trifluoromethyl)phenyl)boronic acid, (4-cyanophenyl The synthesis was the same as that of intermediate L5-3 in Synthesis Example 5, except that boronic acid was used. This method was used to obtain intermediate L16-3 (2.6 g (71% yield)). LC-MS m / z=243(M+H) +

[0232] [Synthesis of intermediate L16-2] The same procedure as in Synthesis Example 1 was repeated except that intermediate L16-3 was used instead of intermediate L5-3. Intermediate L16-2 (2.7 g, yield) was obtained using the same method as in Example 5 for the synthesis of intermediate L5-2. (95%)). LC-MS m / z=271(M+H) +

[0233] [Synthesis of intermediate L16-1] The same procedure as in Synthesis Example 1 was repeated except that intermediate L16-2 was used instead of intermediate L5-2. Intermediate L16-1 (0.6 g, yield) was obtained using the same method as that used for synthesizing intermediate L15-1 in 5. The result was a 25% success rate. LC-MS m / z=239(M+H) +

[0234] [Synthesis of intermediate L16] The same procedure as in Synthesis Example 1 was repeated except that intermediate L16-1 was used instead of intermediate L1-1. Using the same method as that for synthesizing intermediate L1 in 1, intermediate L16 (0.6 g, 85% yield) was obtained. ) was obtained. LC-MS m / z=309(M+H) +

[0235] [Synthesis of intermediate L16Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L16 was used instead of Intermediate L1. The intermediate L16Dimer was obtained using the same method as that for the synthesis of L1Dimer.

[0236] [Synthesis of Compound 16] Except that intermediate L16Dimer was used instead of intermediate L1Dimer. Compound 16 (0.2 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. 40%)). LC-MS m / z=1049(M+H) +

[0237] <Synthesis example 17 (compound 17)> [ka]

[0238] [Synthesis of intermediate L17] Instead of 3,5-dimethylphenylboronic acid, (4-(trifluoromethyl)naphthalene The synthesis method of intermediate L2 in Synthesis Example 2 was repeated except that 2-(2-phenyl-2-methyl-2-boronic acid was used. The same procedure as in Method 1 was used to obtain intermediate L17 (0.9 g (72% yield)). LC-MS m / z=352(M+H) +

[0239] [Synthesis of intermediate L17Dimer] The same procedure as in Synthesis Example 2 was repeated except that intermediate L17 was used instead of intermediate L2. The intermediate L17Dimer was obtained using the same method as that for the synthesis of L2Dimer.

[0240] [Synthesis of Compound 17] Except that intermediate L17Dimer was used instead of intermediate L2Dimer. Compound 17 (0.2 g, yield) was obtained using the same method as that for compound 2 in Synthesis Example 2. 15%)). LC-MS m / z=1105(M+H) +

[0241] <Synthesis example 18 (compound 18)> [ka]

[0242] [Synthesis of intermediate L18] Instead of 3,5-dimethylphenylboronic acid, (4-methylnaphthalen-2-yl) The same method as in Synthesis Example 3 for intermediate L3 was used, except that boronic acid was used. This was used to give intermediate L18 (0.7 g (80% yield)). LC-MS m / z=410(M+H) +

[0243] [Synthesis of Intermediate L18 Dimer] The same procedure as in Synthesis Example 3 was repeated except that Intermediate L18 was used instead of Intermediate L3. The intermediate L18Dimer was obtained using the same method as that for the synthesis of the L3Dimer.

[0244] [Synthesis of Compound 18] Except that intermediate L18Dimer was used instead of intermediate L3Dimer. Compound 18 (0.1 g, yield) was obtained using the same method as that used to synthesize Compound 3 in Synthesis Example 3. 15%)). LC-MS m / z=1221(M+H) +

[0245] <Synthesis example 19 (compound 19)> [ka]

[0246] [Synthesis of intermediate L19] Instead of 3,5-dimethylphenylboronic acid, (4-methylnaphthalen-2-yl) The same method as in Synthesis Example 1 for intermediate L1 was used, except that boronic acid was used. This was used to obtain intermediate L19 (1.2 g (80% yield)). LC-MS m / z=338(M+H) +

[0247] [Synthesis of Intermediate L19 Dimer] The same procedure as in Synthesis Example 1 was repeated except that Intermediate L19 was used instead of Intermediate L1. The intermediate L19Dimer was obtained using the same method as that for the synthesis of the L1Dimer.

[0248] [Synthesis of Compound 19] Except that intermediate L19Dimer was used instead of intermediate L1Dimer. Compound 19 (0.15 g, yield) was obtained using the same method as that for compound 1 in Synthesis Example 1. The result was a 16% success rate. LC-MS m / z=1077(M+H) +

[0249] <<Evaluation Example 1>> For Ir contained in compound 1, the B3LYP / LanL2DZ function was used to calculate the For the organic ligands included in substance 1, the B3LYP / 6-31G(D,P) function was used. The molecular structure of compound 1 was optimized and a Gaussian-based DFT (density functional theory) was used. ) calculation, the two distances between Ir and N in compound 1 (D1(Ir-N) and D2(Ir-N)), and the two distances between Ir and C (D1(Ir-C) and D2(Ir- C)) was evaluated, and Δ(Ir-N) and Δ(Ir-C) of Compound 1 were calculated therefrom. This was repeated for compounds 2 to 19 and compounds A to C, and the results are shown below. The results are summarized in Table 1. [Table 1] TIFF2026042033000100.tif67154TIFF2026042033000101.tif108154TIFF2026042033000102.tif32152TIFF2026042033000103.tif26152

[0250] From Table 1, the sum of Δ(Ir-N) and Δ(Ir-C) for compounds 1 to 19 is 0.002 Å. The sum of Δ(Ir-N) and Δ(Ir-C) of compounds A to C is 0.002 Å. You can be sure that it will exceed that.

[0251] <<Evaluation Example 2>> For Ir contained in compound 1, the B3LYP / LanL2DZ function was used to calculate the For the organic ligands included in substance 1, the B3LYP / 6-31G(D,P) function was used. The molecular structure of compound 1 was optimized and a Gaussian-based DFT (density functional theory) was used. ) calculation, L of compound 1 N and L C Evaluate and then L N / L C Calculate did. Compound 1 L N is a non-hydrogen atom contained in a group bonded to Ir via N and I The maximum distance between compound 1 and r is C is contained in the group bonded to Ir via C. This is the maximum distance between the Ir and the non-hydrogen atom. FIG. 4 shows a group connected to Ir via N and a group connected to Ir via C in Compound 1. 1 is a diagram illustrating the groups and the groups. This was repeated for compounds 1 to 19 and compounds A to C, and the results are shown below. The results are summarized in Table 2. [Table 2]

[0252] From Table 2, L of compounds 1 to 19 N / L C is 1.45 or more, but the L N / L C It can be confirmed that is less than 1.45.

[0253] <<Evaluation Example 3>> Compound H52 and compound 1 were mixed on a quartz substrate in a weight ratio of 98:2. -7 tor After co-evaporation at a vacuum of 1000 rpm to prepare a 50 nm thick film, a sealing glass was placed on the film. A glass plate was attached to seal the film. The film was measured using CoCoLink's Luxol-OLED / analyzer (L OA-100) to measure angle-specific PL (light emission intensity) from -150° to +150° Then, using the analyzer fitting program, the water related to compound 1 was The flat orientation rate was calculated. This was repeated for compounds 2 to 19 and compounds A to C, and the results are shown below. The results are summarized in Table 3. [Table 3]

[0254] From Table 3, it can be seen that the horizontal alignment rates of compounds 1 to 19 are superior to those of compounds A to C. It can be confirmed that this is the case.

[0255] The results of Evaluation Example 1 and Evaluation Example 2 are summarized in Table 4 below (○: Satisfied / ×: Unsatisfied). As stated above. [Table 4]

[0256] Example 1 A glass substrate with ITO patterning was used as the anode, measuring 50 mm x 50 mm x 0. Cut into 0.5mm pieces and rinse with isopropyl alcohol and pure water for over 5 minutes each. After ultrasonic cleaning, the sample was exposed to ultraviolet light and ozone for 30 minutes, and then vacuum deposition was performed. It was installed in the location. HT3 and F6-TCNNQ were co-evaporated in a weight ratio of 98:2 on top of the anode. A hole injection layer with a thickness of 1,350 Å was formed, and HT3 was vacuum-deposited on top of the hole injection layer. A hole transport layer of 1000 ppm was formed. HT21 was vacuum-deposited on the hole transport layer to form an electron blocking layer with a thickness of 300 Å. Next, H52 (host) and Compound 1 (dopant) were mixed in a ratio of 98:2 on top of the electron blocking layer. The layers were co-evaporated in a weight ratio to form a 400 Å thick light-emitting layer. Then, ET3 and ET-D1 were co-deposited on the upper part of the light-emitting layer in a volume ratio of 50:50. ET-D1 was vacuum-deposited on top of the electron transport layer, and a 10 Å thick electron An injection layer is formed, and Al is vacuum-deposited on top of the electron injection layer to form a 1,000 Å thick cathode. By this, ITO (1,500Å) / HT3+F6-TCNNQ (2 wt%) (1 00Å) / HT3(1,350Å) / HT21(300Å) / H52+Compound 1(2wt %)(400Å) / ET3+ET-D1(50%)(350Å) / ET-D1(10Å) An organic light-emitting device with a SiO2 / Al(1,000 Å) structure was fabricated. TIFF2026042033000107.tif109151

[0257] <Examples 2 to 19 and Comparative Examples A to C> When forming the light-emitting layer, the compounds listed in Table 5 were used as dopants instead of Compound 1. An organic light-emitting device was fabricated using the same method as in Example 1, except that the above materials were used. Ta.

[0258] <<Evaluation Example 4>> The organic light-emitting devices manufactured in Examples 1 to 19 and Comparative Examples A to C were driven. Voltage (V), maximum external quantum efficiency (Max EQE) (%), FWQM of EL spectrum ( nm) and lifetime (LT 97 ) (hr) was evaluated, and the results are shown in Table 5 below. The evaluation equipment used was a current / voltage meter (Keithley 2400) and a luminance meter (Mino lta Cs-1000A) is used, and the lifespan (LT 97 ) (at 3,500 nits) The time (hr) required for the brightness to decrease to 97% of the initial brightness of 100% was evaluated. It is a valuable asset. In Table 5, the driving voltage, maximum external quantum efficiency, and lifetime are each expressed as relative values ​​(%). did. (Number 20) Roll-off ratio = {1-(Efficacy at 3,500 nits / Maximum luminous efficacy)} ×100% [Table 5] TIFF2026042033000109.tif108154TIFF2026042033000110.tif32152TIFF2026042033000111.tif26152

[0259] From Table 5, the FWQM of the light emitted from the organic light-emitting devices of Examples 1 to 19 is The FWQM of the light emitted from the organic light-emitting device of Example C is relatively small compared to that of Examples 1 to 19. The organic light-emitting device of this example has higher color purity than the organic light-emitting devices of Comparative Examples A to C. It can be confirmed. Moreover, the organic light-emitting devices of Examples 1 to 19 exhibited improved properties compared to the organic light-emitting devices of Comparative Examples A to C. It has improved drive voltage, improved external quantum efficiency, and improved life characteristics. It can be confirmed.

[0260] The present invention is not limited to the above-described embodiment. It is possible to make various modifications within the scope of the present invention. [Explanation of symbols]

[0261] 10 Organic light-emitting device 11 1st electrode 15 Organic layer 19 2nd electrode

Claims

1. C ２ It has a symmetrical structure, It is represented by the following chemical formula 1: The sum of Δ(Ir-N) and Δ(Ir-C) is 0.002 Å or less. metal compounds. (Chem.1) Ir(L) １ ) ２ (L) ２ Chemical Formula 1 (In the above Chemical Formula 1, L １ is a ligand represented by the following chemical formula 2: L ２ is a ligand represented by the following chemical formula 3: Two L's １ One of them is the 1st L １ The remaining one is the second L １ With ligand can be, The first L １ The ligand and the second L １ the ligands are identical to each other, 【Chemistry 2】 【Transformation 3】 In the above formula 2, Y １ is N and Y ２ is C, In Formula 2, the ring CY １ is a polycyclic group in which three or more 6-membered rings are condensed with each other, In Formula 2, the ring CY ２ is C ５ -C ３０ Carbocyclic group or C １ -C ３０ Heterocyclic group the law of nature, In the chemical formula 2, T １ is the para Hammett substituent constant (σ ｐ ) value is a group that In Formula 2, b1 is an integer of 1 to 10, and when b1 is 2 or more, T １ are either identical to each other or different, In the above formulas 2 and 3, R １ , R ２ , and R ３１ ~R ３３ are, independently of each other, hydrogen, Deuterium, -F, -Cl, -Br, -I, -SF ５ , hydroxyl group, cyano group, nitro group , an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, sulfur a phosphonic acid group or a salt thereof, a phosphate group or a salt thereof, a substituted or unsubstituted C １ -C ６０ Alkyl group, substituted or unsubstituted C ２ -C ６０ Alkenyl group, substituted or unsubstituted C ２ -C ６ ０ Alkynyl group, substituted or unsubstituted C １ -C ６０ Alkoxy groups, substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C １ -C １０ Heterocycloar alkyl group, substituted or unsubstituted C ３ -C １０ Cycloalkenyl groups, substituted or unsubstituted C １ -C １０ heterocycloalkenyl group, substituted or unsubstituted C ６ -C ６０ aryl group , substituted or unsubstituted C ６ -C ６０ aryloxy group, substituted or unsubstituted C ６ -C ６０ arylthio group, substituted or unsubstituted C １ -C ６０ Heteroaryl groups, substituted or represents an unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, groups, -N(Q １ )(Q ２ ), -Si(Q ３ )(Q ４ )(Q ５ ), -Ge(Q ３ )(Q ４ ) (Q ５ ), -B(Q ６ ) (Q ７ ), -P(=O)(Q ８ ) (Q ９ ), or -P(Q ８ ) ( Q ９ ) and In the formula 2, a1 and a2 are each independently an integer of 0 to 10, and a1 is 2. If R is 2 or more, １ are the same or different, and a2 is If it is 2 or more, 2 or more R ２ are either identical to each other or different, In Chemical Formulas 2 and 3, * and *' are the bonding sites with Ir in Chemical Formula 1, respectively. the law of nature, The Δ(Ir—N) is a compound represented by the formulas 1 and 2, which is a compound of Ir and the first L １ Ligand Y １ with distance, Ir, and the second L １ Ligand Y １ is the absolute value of the difference between the distance and The Δ(Ir-C) is a compound represented by the formulas 1 and 2, which is a compound of Ir and the first L １ Ligand Y ２ with distance, Ir, and the second L １ Ligand Y ２ is the absolute value of the difference between the distance and a 1 R １ two or more of the groups may optionally be bonded to each other, and at least one R １ａ Place Substituted or unsubstituted C ５ -C ３０ a carbocyclic group, or at least one R １ａ Replace with or Unsubstituted C １ -C ３０ can form a heterocyclic group, a2 R ２ In the formula, two or more are optionally bonded to each other, and at least one R １ａ in Substituted or unsubstituted C ５ -C ３０ a carbocyclic group, or at least one R １ａ Replace with or is unsubstituted C １ -C ３０ can form a heterocyclic group, R １ and R ２ In the formula, two or more are optionally bonded to each other, and at least one R １ａ substituted or unsubstituted C ５ -C ３０ a carbocyclic group, or at least one R １ａ Replace with or unsubstituted C １ -C ３０ can form a heterocyclic group, R ３１ ~R ３３ In the formula, two or more are optionally bonded to each other, and at least one R １ ａ substituted or unsubstituted C ５ -C ３０ a carbocyclic group, or at least one R １ａ Replace with or unsubstituted C １ -C ３０ can form a heterocyclic group, The R １ａ For an explanation of R １ See the explanation about The substituted C １ -C ６０ Alkyl groups, substituted C ２ -C ６０ Alkenyl group, substituted C was ２ -C ６０ Alkynyl group, substituted C １ -C ６０ Alkoxy groups, substituted C ３ -C １０ Cycloalkyl groups, substituted C １ -C １０ Heterocycloalkyl groups, substituted Retard C ３ -C １０ Cycloalkenyl group, substituted C １ -C １０ Heterocycloalkenyl Group, substituted C ６ -C ６０ Aryl groups, substituted C ６ -C ６０ Aryloxy group, Replaced C ６ -C ６０ Arylthio groups, substituted C １ -C ６０ Heteroaryl groups, substituted Substituents of substituted monovalent non-aromatic fused polycyclic groups and substituted monovalent non-aromatic fused heteropolycyclic groups are independent of each other, Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkini C １ -C ６０ alkoxy groups, Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ a Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q １１ )(Q １２ )、-Si(Q １３ )(Q １４ )(Q １５ )、-Ge(Q １３ )(Q １４ )(Q １５ )、-B(Q １６ )(Q １７ )、-P(=O)(Q １８ )(Q １９ )、-P( Q １８ ) (Q １９ ), or any combination thereof, １ -C ６０ Alkyl Group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group or C １ -C ６０ Alkoxy base, Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , hydroxyl group, cyano group, nitro group, amidino group, hydra a hydroxyl group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or is its salt, C １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkini group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Hetero Cycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkane Nyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Ally Ruthio group, C １ -C ６０ Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic heteroaryl groups (b) condensed 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 ２ ８ ) (Q ２９ ), -P(Q ２８ ) (Q ２９ ), or any combination thereof. or unsubstituted, C ３ -C １０ Cycloalkyl group, C １ -C １０ heterocycloalkyl groups, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６ ０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ３１ )(Q ３２ )、-Si(Q ３３ )(Q ３４ )(Q ３５ )、-Ge(Q ３３ )(Q ３４ )(Q ３５ )、-B(Q ３６ )(Q ３７ )、-P(=O)(Q ３８ )(Q ３９ ), or -P(Q ３８ ) (Q ３９ ),or Any combination thereof, The above Q １ ~Q ９ , Q １１ ~Q １９ , Q ２１ ~Q ２９ , and Q ３１ ~Q ３９ are mutually Independently, Hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group, or its salt, phosphate group or its salt, deuterium, C １ -C ６０ Alkyl group, C ６ -C ６０ Aryl C substituted or unsubstituted with a group, or any combination thereof １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cyclo Alkenyl group, C １ -C １０ Heterocycloalkenyl group, deuterium, C １ -C ６０ Alkyl Group, C ６ -C ６０ aryl groups, or any combination thereof, substituted or unsubstituted C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ arylthio groups, C １ -C ６０ a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic heterofused polycyclic group It is a polycyclic group.)

2. The sum of the Δ(Ir—N) and Δ(Ir—C) is 0 Å to 0.001 Å. The organometallic compound according to claim 1 .

3. L Ｎ is the formula 2, is the maximum distance between an atom other than hydrogen contained in the group represented by the formula (I) and Ir in the formula (I). the law of nature, L Ｃ is the formula 2, is the maximum distance between an atom other than hydrogen contained in the group represented by the law of nature, In the chemical formula, *" represents a bonding site with an adjacent atom, L Ｎ 2. The organometallic reaction system according to claim 1, wherein the / LC is 1.45 to 2.

88. Compound.

4. Said L Ｎ / L Ｃ The organometallic compound according to claim 3, wherein the value of compound.

5. In Formula 2, the ring CY １ is a polycyclic group in which three or four 6-membered rings are fused together, 、 The six-membered ring may be a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyridine group, or a pyridine group.

2. The organic compound according to claim 1, wherein the organic compound is a pyridine group, a pyrazine group, or a pyridazine group. metal compounds.

6. In Formula 2, the ring CY ２ However, benzene group, naphthalene group, 1,2,3,4-tetrahydrofuran Dronaphthalene group, thiophene group, furan group, pyrrole group, cyclopentadiene group, cyclopentadiene group benzothiophene group, benzofuran group, indole group, indene group, benzosiloxane group dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, or 2. The organometallic compound according to claim 1, wherein is a dibenzosilole group.

7. In the chemical formula 2, T １ teeth, a fluoro group (—F) or a cyano group, or Deuterium, fluoro group, cyano group, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkane group, C １ -C １０ heterocycloalkyl group, phenyl group, biphenyl group, or any of these groups Fluorinated C, substituted or unsubstituted in any combination １ -C ２０ Alkyl group, fluorinated C ３ -C １０ Cycloalkyl groups, fluorinated C １ -C １０ Heterocycloalkyl groups, fluorinated phenyl groups C containing phenyl group, fluorinated biphenyl group, and cyano group １ -C ２０ Alkyl group, cyano group-containing C ３ - C １０ Cycloalkyl group, cyano group-containing C １ -C １０ Heterocycloalkyl group, cyano group 2. The compound according to claim 1, wherein the compound is a phenyl group containing a cyano group or a biphenyl group containing a cyano group. Organometallic compounds of.

8. The above R １ , R ２ and R ３１ ~R ３３ are independent of each other, hydrogen, deuterium, —F, or a cyano group; Deuterium, -F, cyano group, C １ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, C １ -C １０ a heterocycloalkyl group, a phenyl group, a biphenyl group, or any of them; substituted or unsubstituted in combination, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloal Kill group, C １ -C １０ a heterocycloalkyl group, a phenyl group, or a biphenyl group; -Si(Q ３ ) (Q ４ ) (Q ５ ) or -Ge(Q ３ ) (Q ４ ) (Q ５ ) 2. The organometallic compound according to claim 1 .

9. In the above Chemical Formula 2, 【change】 is a group represented by one of the following chemical formulas 2-1 to 2-21.

2. The organometallic compound according to claim 1, wherein 【Chemistry 2-1-2-6】 【Chemistry 2-7-2-12】 【Chemistry 2-13-2-18】 【Chemistry 2-19-2-21】 (In the above chemical formulas 2-1 to 2-21, Y １ is N, X １ ~X １０ are each independently C or N, and the chemical formulas 2-1 to 2-9 and X in Formula 2-21 １ ~X ８ At least one of the formulas 2-10 to 2-20 is C. X １ ~X １０ at least one of is C, * is a bonding site with Ir in Chemical Formula 1, *" is a bonding site with an adjacent atom.)

10. In the above Chemical Formula 2, 【change】 is a group represented by one of the following chemical formulas 2(1) to 2(75):

2. The organometallic compound according to claim 1 . 【Chemistry 2(1)-2(12)】 【Chemistry 2(13)-2(24)】 【Chemistry 2(25)-2(36)】 【Chemistry 2(37)-2(48)】 【Chemistry 2(49)-2(54)】 【Chemistry 2(55)-2(60)】 【Chemistry 2(61)-2(66)】 【Chemistry 2(67)-2(72)】 【Chemistry 2(73)-2(75)】 (In the above chemical formulas 2(1) to 2(75), Y １ is N, X １１ is C(R １１ ) or N, and X １２ is C(R １２ ) or N, and X １３ is C(R １３ ) or N, and X １４ is C(R １４ ) or N, and X １５ is C ( R １５ ) or N, and X １６ is C(R １６ ) or N, and X １７ is C(R １７ ) or N, and X １８ is C(R １８ ) or N, and X １９ is C(R １９ ) or N Yes, X １９ａ is C(R １９ａ ) or N, The R １１ ~ The above R １９ , and the R １９ａ The explanations for each are given in the claims. Te, R １ See the explanation about T １１ and T １２ The explanation for each of the above is as follows: １ Explanation about Refer to * is a bonding site with Ir in Chemical Formula 1, *" is a bonding site with an adjacent atom.)

11. In the above Chemical Formula 1, 【change】 is a group represented by one of the following chemical formulas CY2-1 to CY2-10: The organometallic compound according to claim 1, 【Chemical CY2-1-CY2-8】 【Chemical CY2-9-CY2-10】 (In the above chemical formulas CY2-1 to CY2-10, Y ２ is C, X ２１ is O, S, N (R ７ ), C(R ２７ ) (R ２８ ), or Si(R ２７ ) (R ２ ８ ) and R ２１ ~R ２８ The explanation for each of these is given in claim 1, ２ Explanation about See, *' is a bonding site with Ir in Chemical Formula 1, *" is a bonding site with an adjacent atom in Chemical Formula 1.)

12. In the above Chemical Formula 1, is a group represented by the chemical formula CY2-1 or CY2-8. The organometallic compound according to claim 11.

13. In the formula CY2-1, R ２１ and R ２３ are independently deuterium, C １ -C ２ ０ Alkyl group, C ３ -C １０ Cycloalkyl group, C １ -C １０ heterocycloalkyl groups, C substituted or unsubstituted with a phenyl group, a biphenyl group, or any combination thereof １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl group, C １ -C １０ Heterocycloar 12. The organic compound according to claim 11, wherein the alkyl group is an alkyl group, a phenyl group, or a biphenyl group. metal compounds.

14. The present invention is characterized by satisfying the following conditions 4 and 5, or a combination thereof. The organometallic compound according to claim 1 . (<Condition 4> In Formula 3, R ３１ is a group represented by the following chemical formula 4. <Condition 5> In Formula 3, R ３２ is a group represented by the following chemical formula 5. 【Chemistry 4】 【Transformation 5】 In the formulas 4 and 5, A １ ~A ６ are, independently of each other, hydrogen or deuterium, or Deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl groups, biphenyls C substituted or unsubstituted with phenyl groups, or any combination thereof １ -C ２０ Archi group, C ３ -C １０ Cycloalkyl group, C ６ -C ６０ Aryl group, C １ -C ６０ Heteroa an aryl group, a phenyl group, or a biphenyl group; * indicates a bonding site with an adjacent atom.)

15. The chemical formula 4 satisfies one of the following conditions 4-1 to 4-6: 、 The chemical formula 5 satisfies one of the following conditions 5-1 to 5-6:

15. The organometallic compound according to claim 14, (<Condition 4-1> A １ ~A ３ is not hydrogen at the same time. <Condition 4-2> A １ ~A ３ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Shik and substituted or unsubstituted with alkyl, phenyl, biphenyl, or any combination thereof. is unsubstituted, C １ -C ２０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, or It is a biphenyl group. <Condition 4-3> A １ and A ２ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; or unsubstituted, C １ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, phenyl groups, or a biphenyl group, A ３ is deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl C, substituted or unsubstituted with a group, a biphenyl group, or any combination thereof ２ -C ２ ０ Alkyl group, C ３ -C １０ It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-4> A １ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloal substituted or unsubstituted alkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Exchange, C １ -C ２０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, or a biphenyl group is a phenyl group, A ２ and A ３ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; or unsubstituted, C ２ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, phenyl groups, Or a biphenyl group. <Condition 4-5> A １ is hydrogen, deuterium, -CH ３ , -CH ２ D, -CHD ２ , or -CD ３ and A ２ is deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl C, substituted or unsubstituted with a group, a biphenyl group, or any combination thereof １ -C ２ ０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, or a biphenyl group; A ３ is deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl C, substituted or unsubstituted with a group, a biphenyl group, or any combination thereof ２ -C ２ ０ Alkyl group, C ３ -C １０ It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 4-6> A １ is hydrogen, deuterium, -CH ３ , -CH ２ D, -CHD ２ , or -CD ３ and A ２ and A ３ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; or unsubstituted, C ２ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, phenyl groups, Or a biphenyl group. <Condition 5-1> A ４ ~A ６ is not hydrogen at the same time. <Condition 5-2> A ４ ~A ６ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Shik and substituted or unsubstituted with alkyl, phenyl, biphenyl, or any combination thereof. is unsubstituted, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl groups, or is a biphenyl group. <Condition 5-3> A ４ and A ５ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; or unsubstituted, C １ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, phenyl groups, or a biphenyl group, A ６ is deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl C, substituted or unsubstituted with a group, a biphenyl group, or any combination thereof ２ -C ２ ０ Alkyl group, C ３ -C １０ It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-4> A ４ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloal substituted or unsubstituted alkyl groups, phenyl groups, biphenyl groups, or any combination thereof; Exchange, C １ -C ２０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, or a biphenyl group is a phenyl group, A ５ and A ６ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; or unsubstituted, C ２ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, phenyl groups, Or a biphenyl group. <Condition 5-5> A ４ is hydrogen, deuterium, -CH ３ , -CH ２ D, -CHD ２ , or -CD ３ and A ５ is deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl C, substituted or unsubstituted with a group, a biphenyl group, or any combination thereof １ -C ２ ０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, or a biphenyl group; A ６ is deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ Cycloalkyl groups, phenyl C, substituted or unsubstituted with a group, a biphenyl group, or any combination thereof ２ -C ２ ０ Alkyl group, C ３ -C １０ It is a cycloalkyl group, a phenyl group, or a biphenyl group. <Condition 5-6> A ４ is hydrogen, deuterium, -CH ３ , -CH ２ D, -CHD ２ , or -CD ３ and A ５ and A ６ are independently deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ S substituted with cycloalkyl groups, phenyl groups, biphenyl groups, or any combination thereof; or unsubstituted, C ２ -C ２０ Alkyl group, C ３ -C １０ cycloalkyl groups, phenyl groups, or a biphenyl group.

16. R of Formula 3 ３１ ~R ３３ At least one of the following is independently selected from deuterium, C １ -C ２０ Alkyl group, C ３ -C １０ a cycloalkyl group, a phenyl group, a biphenyl group, or any combination thereof, substituted or unsubstituted C ３ -C １０ is a cycloalkyl group 2. The organometallic compound according to claim 1 .

17. A first electrode; A second electrode; an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; The organic layer contains one or more organometallic compounds according to any one of claims 1 to 16. An organic light-emitting device comprising:

18. the first electrode is an anode; the second electrode is a cathode; The organic layer includes a hole transport region disposed between the first electrode and the light-emitting layer, and further comprising an electron transport region disposed between the light-emitting layer and the second electrode; The hole transport region may be a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any of these. any combination of The electron transport region may be a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. The organic light-emitting device according to claim 17, comprising a laminate.

19. 18. The photosensitive material according to claim 17, wherein the organometallic compound is contained in the light-emitting layer. Light emitting element.

20. An electronic device comprising the organic light-emitting device according to any one of claims 17 to 19. Device.

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