Titanium complex compound and organic light emitting device comprising same

Abstract

One aspect of the present invention relates to a titanium complex compound represented by chemical formula 1 and an organic light emitting device comprising same. The titanium complex compound according to one aspect can overcome the low luminous efficiency and instability of existing titanium-based light emitters and realize significantly improved luminous properties. [Chemical formula 1] (In Chemical Formula 1, Y1, Y2, R1 to R7 and p to r are as described in the specification.)

Description

Titanium complex and organic light-emitting device containing the same

[0001] The present disclosure relates to a titanium complex compound and an organic light-emitting device comprising the same.

[0002] Transition metal-based light-emitting diodes (L-emitting diodes) possess high luminescence efficiencies and can have their luminescence properties tunable by ligands, making them widely studied as materials for optoelectronic devices. Precious metal complexes, such as iridium (Ir), ruthenium (Ru), and platinum (Pt), offer superior luminescence properties and are therefore highly versatile. However, these precious metal elements exist in only trace amounts on Earth, leading to high costs and resource depletion, and critical limitations in terms of sustainability.

[0003] Accordingly, there is a growing demand for the development of alternative luminescent materials utilizing earth-abundant elements such as iron (Fe) and titanium (Ti). Titanium is a low-toxicity, stable, and sustainable material that has attracted attention in various research fields. However, little research has been conducted on titanium complexes with stable luminescent properties, and the titanium complexes reported to date have limited luminescent efficiencies of less than 1%. In particular, luminescent materials with long luminescent lifetimes mainly rely on complexes of noble metals with high spin-orbit coupling, and replacing them with sustainable first-period transition metals is difficult due to the inherent limitations of the central metal.

[0004] One aspect of the present invention provides a titanium complex compound having a novel structure that can be usefully used as a blue light-emitting material and a method for producing the same.

[0005] Another aspect of the present invention provides an organic light-emitting device employing the titanium complex compound as a light-emitting layer material.

[0006] One aspect of the present invention provides a titanium complex represented by the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] (In the above chemical formula 1,

[0010] R 1 Inland R 3 are each independently C1-C20 alkyl, C1-C20 alkoxy or halogen;

[0011] p to r are each independently integers from 0 to 3;

[0012] Y 1 and Y 2 are each independently hydrogen, C1-C20 alkyl, C6-C20 aryl, C2-C20 heteroaryl, and the Y 1 and Y 2 Alkyl, aryl and heteroaryl of *-NR 8 N 9 can be further substituted with;

[0013] R 4 Inland R 9 are each independently C1-C20 alkyl or C6-C20 aryl.)

[0014] According to one aspect, the titanium complex compound may be represented by the following chemical formula 2.

[0015] [Chemical Formula 2]

[0016]

[0017] (In the above chemical formula 2,

[0018] R 1 , R 4 Inland R 7 , Y 1 and Y 2 is the same as the above definition.)

[0019] Above Y 1 and Y 2 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl, or C2-C12 heteroaryl, or may be selected from the following structures.

[0020]

[0021] (In the above structure, R8 and R 9 are each independently C1-C10 alkyl or C6-C12 aryl.)

[0022] According to one aspect, the titanium complex compound may be represented by the following chemical formula 3.

[0023] [Chemical Formula 3]

[0024]

[0025] (In the above chemical formula 3,

[0026] R 1 is C1-C10 alkyl, C1-C10 alkoxy or halogen;

[0027] R 4 Inland R 9 are each independently C1-C10 alkyl or C6-C12 aryl.)

[0028] According to one aspect, the titanium complex compound may be represented by the following chemical formula 4.

[0029] [Chemical Formula 4]

[0030]

[0031] (In the above chemical formula 4,

[0032] R 1 is C1-C7 alkyl, C1-C7 alkoxy or halogen;

[0033] R is C1-C7 alkyl or C6-C12 aryl.)

[0034] The above R 1 is branched C3-C7 alkyl, C1-C7 alkoxy or halogen; R can be C1-C7 alkyl or C6-C12 aryl.

[0035] The titanium complex according to one aspect may be selected from the following structures.

[0036]

[0037]

[0038]

[0039] According to one aspect, the titanium complex compound may have a photoluminescence quantum efficiency of 30% or more.

[0040] Another aspect of the present invention provides an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the electrodes, wherein the organic layer comprises the titanium complex compound.

[0041] In an organic light-emitting device according to one aspect, the organic layer containing the titanium complex compound may be a light-emitting layer.

[0042] Titanium complexes according to one mode can overcome the low luminescence efficiency and instability of existing titanium-based luminescent materials and achieve significantly improved luminescence properties. In particular, titanium complexes according to one mode exhibit excellent blue phosphorescence efficiency and can be utilized as blue luminescent materials, which previously relied heavily on precious metal complexes.

[0043] In addition, titanium complexes according to one aspect can drastically reduce production costs by utilizing titanium, an abundant metallic element, are sustainable, and have excellent luminous efficiency and lifespan characteristics, making them advantageous for commercialization and expected to be useful in fields such as the display and lighting industries.

[0044] In other words, titanium complexes according to one aspect have advantages in environmental, economic, and technological aspects, and can offer a wide range of application possibilities as next-generation luminescent materials.

[0045] Figure 1 illustrates the results of an evaluation of the luminescence spectrum of a titanium complex according to Example 1.

[0046] Figure 2 illustrates the results of evaluating the luminescence lifetime of a titanium complex according to Example 1.

[0047] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0048] As used herein, the singular forms may be intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0049] Throughout this specification, the terms "comprises," "includes," "contains," or "has" a component, unless specifically stated to the contrary, do not exclude other components, but rather may include other components, and do not exclude additional unrecited elements, materials, or processes.

[0050] The numerical ranges used herein include the lower and upper limits and all values ​​within that range, increments logically derived from the shape and width of the defined range, all doubly defined values, and all possible combinations of the upper and lower limits of numerical ranges defined in different shapes. Unless otherwise specified herein, values ​​outside the defined range that may arise due to experimental error or rounding of values ​​are also included in the defined numerical range.

[0051] Unless otherwise specified herein, “about” may be considered a value within 30%, 25%, 20%, 15%, 10% or 5% of the stated value.

[0052] In this specification, substituents including “alkyl”, “alkoxy” and other “alkyl” moieties include both straight-chain and branched forms.

[0053] Below, the present disclosure will be described in detail. However, this is merely exemplary and the present disclosure is not limited to the specific embodiments described as examples.

[0054] One aspect of the present invention provides a titanium complex compound capable of implementing excellent luminescent properties, and specifically, the titanium complex compound according to one aspect can be represented by the following chemical formula 1.

[0055] [Chemical Formula 1]

[0056]

[0057] (In the above chemical formula 1,

[0058] R 1 Inland R 3 are each independently C1-C20 alkyl, C1-C20 alkoxy or halogen;

[0059] p to r are each independently integers from 0 to 3;

[0060] Y 1 and Y 2 are each independently hydrogen, C1-C20 alkyl, C6-C20 aryl, C2-C20 heteroaryl, and the Y 1 and Y 2 Alkyl, aryl and heteroaryl of *-NR 8 N 9 can be further substituted with;

[0061] R 4 Inland R 9 are each independently C1-C20 alkyl or C6-C20 aryl.)

[0062] The titanium complex according to one embodiment, having the structural characteristics described above, can overcome the technical limitations of low luminescence efficiency and instability of existing titanium-based luminescent materials and realize significantly improved luminescence characteristics. In particular, the titanium complex according to one embodiment has excellent blue phosphorescence efficiency and can be utilized as a blue luminescent material that has previously been highly dependent on existing noble metal complexes.

[0063] For example, the photoluminescence quantum yield of the titanium complex may be 30% or more, or 40% or more, or 50% or more, 60% or more, or 70% or more, and specifically 30% to 90%, or 40% to 90%, or 50% to 90%, or 50% to 80%.

[0064] For example, the above R 1 Inland R 3 Each may independently be C1-C10 alkyl, C1-C10 alkoxy or halogen, and specifically may be C1-C7 alkyl, C1-C7 alkoxy or halogen.

[0065] According to one aspect, the titanium complex compound may be represented by the following chemical formula 2.

[0066] [Chemical Formula 2]

[0067]

[0068] (In the above chemical formula 2,

[0069] R 1 is C1-C20 alkyl, C1-C20 alkoxy or halogen;

[0070] Y 1 and Y 2 are each independently hydrogen, C1-C20 alkyl, C6-C20 aryl, C2-C20 heteroaryl, and the Y 1 and Y 2 Alkyl, aryl and heteroaryl of *-NR 8 N 9 can be further substituted with;

[0071] R 4 Inland R 9 are each independently C1-C20 alkyl or C6-C20 aryl.)

[0072] For example, the above R 1may be C1-C10 alkyl, C1-C10 alkoxy or halogen, and specifically may be C1-C7 alkyl, C1-C7 alkoxy or halogen.

[0073] For example, the above R 4 Inland R 7 Each of which may independently be C1-C10 alkyl or C6-C12 aryl, specifically, C1-C7 alkyl, or C1-C4 alkyl, or C1-C3 alkyl, or phenyl.

[0074] For example, the above Y 1 and Y 2 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl, or C2-C12 heteroaryl, or may be selected from the following structures.

[0075]

[0076] In the above structure, R 8 and R 9 Each may independently be C1-C10 alkyl or C6-C12 aryl, specifically, C1-C7 alkyl, or C1-C4 alkyl, or C1-C3 alkyl, or phenyl.

[0077] Specifically, the titanium complex compound according to one aspect may be represented by the following chemical formula 3.

[0078] [Chemical Formula 3]

[0079]

[0080] (In the above chemical formula 3,

[0081] R 1 is C1-C20 alkyl, C1-C20 alkoxy or halogen;

[0082] R 4 Inland R 9 are each independently C1-C20 alkyl or C6-C20 aryl.)

[0083] For example, the above R 4 Inland R 9Each of R may independently be C1-C10 alkyl or C6-C12 aryl, specifically, C1-C7 alkyl, or C1-C4 alkyl, or C1-C3 alkyl, or phenyl, and R 4 Inland R 9 can be identical to each other.

[0084] Specifically, the titanium complex according to one aspect may be represented by the following chemical formula 4.

[0085] [Chemical Formula 4]

[0086]

[0087] (In the above chemical formula 4,

[0088] R 1 is C1-C20 alkyl, C1-C20 alkoxy or halogen;

[0089] R is C1-C20 alkyl or C6-C20 aryl.)

[0090] For example, the above R 1 may be C1-C7 alkyl, C1-C7 alkoxy or halogen, and specifically, R 1 is branched C3-C7 alkyl, C1-C7 alkoxy or halogen; R can be C1-C7 alkyl or C6-C12 aryl.

[0091] For example, the R may be C1-C7 alkyl or C6-C12 aryl, and specifically, the R may be C1-C4 alkyl or C1-C3 alkyl.

[0092] For example, the titanium complex according to one aspect may be selected from the following structures, but is not limited thereto.

[0093]

[0094]

[0095]

[0096] Titanium complexes according to one aspect can be prepared using materials and reaction conditions known in the art.

[0097] Another aspect of the present invention provides an organic light-emitting device comprising the titanium complex. In this case, the organic light-emitting device is composed of a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode. The organic layers may have a single-layer structure consisting of one layer, but may also have a multilayer structure consisting of two or more layers including a light-emitting layer. When the organic layers of the organic light-emitting device have a multilayer structure, this may be, for example, a structure in which a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, etc. are laminated. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0098] The above organic layer may include a compound according to one aspect.

[0099] The organic layer may include a light-emitting layer, and the light-emitting layer may include a titanium complex compound according to one embodiment, and the titanium complex compound according to one embodiment may be included as a host material in the light-emitting layer. When the titanium complex compound according to one embodiment is included as a host material in the light-emitting layer, the light-emitting layer may include one or more dopants.

[0100] It goes without saying that the organic light-emitting device according to one aspect can be manufactured by any possible method within the scope recognizable by a person skilled in the art.

[0101] The titanium complex according to one aspect can be applied to various organic light-emitting devices, and the organic light-emitting devices can be used in devices selected from, but not limited to, flat panel display devices, flexible display devices, flat panel lighting devices of single color or white color, and flexible lighting devices of single color or white color.

[0102] Below, organic light-emitting devices according to one aspect are described in more detail, but are not limited thereto.

[0103] An organic light-emitting device according to one embodiment may include an anode, a cathode, and an organic layer disposed therebetween. In addition, the organic layer of the above-described organic light-emitting device may include at least one of an auxiliary layer (buffer layer), a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and, except for including a titanium complex compound according to one embodiment of the present invention in the organic layer, may be manufactured in a structure known in the art using a manufacturing method and materials commonly used in the art, so a detailed description thereof will be omitted.

[0104] Hereinafter, the above-described implementation examples will be described in more detail through examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0105] [Manufacturing Example 1]

[0106]

[0107] 2.23 g (10 mmol) of diethyl pyridine-2,6-dicarboxylate, 3.0 g (29.4 mmol) of pivalic acid, 0.87 mL (16.3 mmol) of sulfuric acid, 170 mg (1 mmol) of silver nitrate (AgNO3), and 7.0 g (29.4 mmol) of sodium persulfate (Na2S2O8) were added to 100 mL of water and stirred at room temperature for 24 hours. After the reaction was completed, an aqueous sodium bicarbonate solution was added. The obtained aqueous layer was extracted three times with 20 mL of ethyl acetate (EA), and the combined organic layers were dried over magnesium sulfate and the solvent was evaporated. The residue obtained was separated and purified by silica gel column chromatography to obtain 2.33 g (yield 83.5%) of intermediate compound a.

[0108] 1 H NMR (600 MHz, CDCl3) δ 8.27 (s, 2H), 4.49 (q, J = 7.0 Hz, 4H), 1.47 (t, J = 7.1 Hz, 6H), 1.39 (s, 9H).

[0109] [Manufacturing Example 2]

[0110]

[0111] 2.01 g (10 mmol) of 4-hydroxypyridine-2,6-dicarboxylic acid, 3 drops of dimethylformamide (DMF), and 15 mL of thionyl chloride (SOCl2) were added and stirred under reflux for 2 hours to allow the reaction. After the reaction was completed, the solvent was evaporated to obtain 2.3 g (yield 96.6%) of intermediate compound b.

[0112] 1 H NMR (600 MHz, CDCl3) δ 8.31 (s, 2H).

[0113] [Manufacturing Example 3]

[0114]

[0115] 1.46 g (6.1 mmol) of intermediate compound b was added to 8 mL of ethanol and stirred at room temperature for 1 hour to react. After the reaction was completed, an aqueous sodium chloride solution was added. The obtained aqueous layer was extracted three times with 20 mL of dichloromethane (DCM), and the combined organic layers were dried over magnesium sulfate and the solvent was evaporated to obtain 1.42 g (yield 90.0%) of intermediate compound c.

[0116] 1 H NMR (600 MHz, CDCl3) δ 8.26 (s, 2H), 4.50 (q, J = 7.1 Hz, 4H), 1.46 (t, J = 7.2 Hz, 6H).

[0117] [Manufacturing Example 4]

[0118]

[0119] 1.0 g (5 mmol) of 4-hydroxypyridine-2,6-dicarboxylic acid, 0.17 mL (3.1 mmol) of sulfuric acid (H2SO4) and 10 mL of methanol were added and stirred under reflux for 4 hours. After the reaction was completed, an aqueous sodium bicarbonate solution was added. The obtained aqueous layer was extracted three times with 20 mL of ethyl acetate (EA), and the combined organic layer was dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 282 mg (yield 25.1%) of intermediate compound d.

[0120] 1 H NMR (600 MHz, DMSO-d6) δ 7.74 (s, 2H), 3.98 (s, 3H), 3.91 (s, 6H).

[0121] [Example 1] Titanium complex (1)

[0122]

[0123] Preparation of compound (1)-A

[0124] 500 mg (2.24 mmol) of diethyl pyridine-2,6-dicarboxylate, 1.0 g (10.08 mmol) of 4-bromo-N,N-dimethylaniline, 500 mg of magnesium turnings, and 3 mg of iodine were added to 20 mL of tetrahydrofuran (THF) and stirred under reflux for 14 hours. After the reaction was completed, an aqueous ammonium chloride solution was added. The obtained aqueous layer was extracted three times with 20 mL of ethyl acetate (EA), and the combined organic layer was dried over magnesium sulfate, and the solvent was evaporated. The residue obtained was separated and purified by silica gel column chromatography to obtain 580 mg (yield 42.1%) of compound (1)-A.

[0125] 1 H NMR (600 MHz, CD2Cl2) δ 7.54 (t, J = 7.5 Hz, 1H), 7.04 (d, J = 8.9 Hz, 8H), 7.01 (d, J = 7.8 Hz, 2H), 6.63 (d, J = 8.8 Hz, 8H), 4.89 (s, 2H), 2.92 (s, 24H).

[0126] Preparation of titanium complex (1)

[0127] Compound (1)-A 100 mg (0.162 mmol) and titanium (IV) isopropoxide 23 mg (0.081 mmol) were added to toluene and reacted by reflux stirring for 17 hours. After completion of the reaction, the mixture was concentrated and recrystallized to obtain 79.2 mg (yield 76.7%) of titanium complex compound (1).

[0128] 1H NMR (600 MHz, CD2Cl2) δ 7.71 (t, J = 7.7 Hz, 2H), 7.34 (d, J = 7.8 Hz, 4H), 7.18 (d, J = 8.8 Hz, 16H), 6.41 (d, J = 8.9 Hz, 16H), 2.86 (s, 48H).

[0129] [Example 2] Titanium complex (2)

[0130]

[0131] Preparation of compound (2)-A

[0132] 1.76 g (8.8 mmol) of 4-bromo-N,N-dimethylaniline, 500 mg of magnesium turnings, 3 mg of iodine, and 20 mL of THF were added and reacted by refluxing for 3 hours. After that, 558.7 mg (2.0 mmol) of the intermediate compound a obtained in Preparation Example 1 was dissolved in 10 mL of THF, and this solution was slowly added dropwise to the stirred solution, and reacted by refluxing for 15 hours. After the reaction was completed, an aqueous ammonium chloride solution was added. The obtained aqueous layer was extracted three times with 20 mL of ethyl acetate (EA), and the collected organic layer was dried with magnesium sulfate, and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain 1.04 g (yield 77.8%) of compound (2)-A.

[0133] 1 H NMR (600 MHz, CD2Cl2) δ 7.08 (s, 2H), 7.05 (d, J = 8.8 Hz, 8H), 6.63 (d, J = 8.8 Hz, 8H), 4.90 (s, 2H), 2.92 (s, 24H), 1.14 (s, 9H).

[0134] Preparation of titanium complex (2)

[0135] Compound (2)-A 180 mg (0.268 mmol) and titanium (IV) isopropoxide 37.8 mg (0.134 mmol) were added to toluene and reacted by reflux stirring for 3 hours. After completion of the reaction, the mixture was concentrated and recrystallized to obtain 173.8 mg (yield 93.5%) of titanium complex compound (2).

[0136] 1 H NMR (600 MHz, CD2Cl2) δ 7.41 (s, 4H), 7.16 (d, J = 8.9 Hz, 16H), 6.39 (d, J = 8.9 Hz, 16H), 2.86 (s, 48H), 1.24 (s, 18H).

[0137] [Example 3] Titanium complex (3)

[0138]

[0139] The same procedure as in Example 2 was followed except that 4-bromo-N,N-diphenylaniline was used instead of 4-bromo-N,N-dimethylaniline.

[0140] 1 H NMR (600 MHz, THF-d8) δ 7.39 (s, 4H), 7.20 (d, J = 8.7 Hz, 16H), 7.05 (dd, J = 8.5, 7.3 Hz, 32H), 6.92 - 6.88 (m, 32H), 6.85 (t, J = 7.4 Hz, 16H), 6.76 - 6.71 (m, 16H), 1.24 (s, 18H).

[0141] [Example 4] Titanium complex (4)

[0142]

[0143] The same procedure was followed, except that intermediate compound c obtained in Preparation Example 3 was used instead of intermediate compound a in Example 2.

[0144] 1 H NMR (600 MHz, CDCl3) δ 7.30 (s, 4H), 7.18 (d, J = 8.8 Hz, 16H), 6.40 (d, J = 9.0 Hz, 16H), 2.86 (s, 48H).

[0145] [Example 5] Titanium complex (5)

[0146]

[0147] The same procedure was followed, except that intermediate compound d obtained in Manufacturing Example 4 was used instead of intermediate compound a in Example 2.

[0148] 1 H NMR (600 MHz, CDCl3) δ 7.23 (d, J = 8.5 Hz, 16H), 6.76 (s, 4H), 6.43 (s, 16H), 3.71 (s, 6H), 2.87 (s, 48H).

[0149] <Evaluation of luminescence characteristics>

[0150] Each of the titanium complexes obtained in the above examples was diluted in 1,2-dichlorobenzene to a concentration that gave an absorbance of 0.1 at 375 nm, and the emission spectrum was measured by exciting at a wavelength of 375 nm at room temperature using a lifetime measurement fluorescence spectrometer (Horiba fluoromax plus) (Fig. 1), and the obtained maximum emission wavelength (λ max ) and the luminescence lifetime at the maximum luminescence wavelength was measured (Fig. 2), and the results are shown in Table 1 below.

[0151] In addition, by calculating the photon emission and absorption ratio of the titanium complex of Example 2 compared to the reference using the solvent conditions as a reference, the photoluminescence quantum efficiency of the titanium complex was measured, and it was confirmed that an excellent efficiency of 70.2% was achieved.

[0152] Titanium complex 12345λ max(nm)509492474534489 Luminous lifetime (ns)571.8397.872.778.2126.4

[0153] Referring to the above luminescence characteristic evaluation, it can be seen that the titanium complex compounds according to the examples of the present invention all exhibit maximum luminescence wavelengths in the blue to green range and have excellent luminescence characteristics in a solution at room temperature. In addition, it can be seen that the titanium complex compounds according to the examples have a photoluminescence quantum efficiency of 70% or more, which is significantly improved luminescence efficiency compared to existing titanium-based organic luminescent materials that have luminescence efficiencies of less than 1%. In other words, it was confirmed that the titanium complex compounds according to the present invention have excellent luminescence characteristics that are commercializable.

[0154] Although the present disclosure has been described with specific details and limited examples, these are provided only to help a more general understanding of the present disclosure, and the present disclosure is not limited to the above examples, and those skilled in the art to which the present disclosure pertains can make various modifications and variations based on these descriptions.

[0155] Therefore, the present disclosure should not be limited to the embodiments described above, and all things that are equivalent or equivalent to the claims described below as well as the same are included in the scope of the present disclosure.

Claims

1. Titanium complex represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R 1 Inland R 3 are each independently C1-C20 alkyl, C1-C20 alkoxy or halogen; p to r are each independently an integer from 0 to 3; Y 1 and Y 2 are each independently hydrogen, C1-C20 alkyl, C6-C20 aryl, C2-C20 heteroaryl, and Y 1 and Y 2 Alkyl, aryl and heteroaryl of *-NR 8 N 9 can be further substituted with; R 4 Inland R 9 are each independently C1-C20 alkyl or C6-C20 aryl.

2. In paragraph 1, A titanium complex compound represented by the following chemical formula 2: [Chemical formula 2] In the above chemical formula 2, R 1 , R 4 Inland R 7 , Y 1 and Y 2 is the same as the definition in paragraph 1 above.

3. In paragraph 1, Above Y 1 and Y 2 A titanium complex, wherein each independently represents hydrogen, C1-C10 alkyl, C6-C12 aryl, or C2-C12 heteroaryl, or is selected from the following structures: In the above structure, R 8 and R 9 are each independently C1-C10 alkyl or C6-C12 aryl.

4. In paragraph 1, A titanium complex compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, R 1 is C1-C10 alkyl, C1-C10 alkoxy or halogen; R 4 Inland R 9 are each independently C1-C10 alkyl or C6-C12 aryl.

5. In paragraph 1, A titanium complex compound represented by the following chemical formula 4: [Chemical Formula 4] In the above chemical formula 4, R 1 is C1-C7 alkyl, C1-C7 alkoxy or halogen; R is C1-C7 alkyl or C6-C12 aryl.

6. In paragraph 5, Above R 1 A titanium complex, wherein R is branched C3-C7 alkyl, C1-C7 alkoxy or halogen; and R is C1-C7 alkyl or C6-C12 aryl.

7. In paragraph 1, A titanium complex selected from the following structures.

8. In paragraph 1, The above titanium complex compound is a titanium complex compound having a photoluminescence quantum efficiency of 30% or more.

9. An organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the electrodes, An organic light-emitting device, wherein the organic layer comprises a titanium complex compound selected from any one of claims 1 to 8.

10. In paragraph 9, An organic light-emitting device, wherein the organic layer containing the titanium complex compound is a light-emitting layer.

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