KR101739831B1 - Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus - Google Patents

Abstract

상기 식에서, R1, R2, R3, R4, L, n 및 Het는 전술하여 정의된 바와 같다.There is provided an organic light-emitting compound represented by the following formula (1).
[Chemical Formula 1]

Wherein R1, R2, R3, R4, L, n and Het are as defined above.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, an ink composition, an organic light emitting device, and an electronic device.

An organic light-emitting compound, an ink composition, an organic light-emitting device and an electronic device.

An electroluminescence device (EL device) is a self-emissive type display device having a high response speed and a wide viewing angle. In 1987, Eastman Kodak Company first developed an organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer material [Appl. Phys. Lett. 51, 913, 1987].

The most important factor for determining the luminous efficiency in an OLED is a luminescent material, and a phosphorescent material in a luminescent material can improve luminous efficiency up to 4 times the theoretical value of a fluorescent material. Until now, iridium (III) complexes and carbazole-based materials have been widely known as phosphorescent materials, and new phosphorescent materials are being studied in recent years.

The principle of the organic electroluminescent phenomenon is that when a voltage is applied between two electrodes when an organic material layer exists between the cathode and the anode, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic layer are recombined to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As materials used in organic light emitting devices, pure organic materials or complexes in which an organic material and a metal form a complex are mostly used, and they are classified into a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material which is easily oxidized and electrochemically stable at the time of oxidation, is mainly used. On the other hand, as an electron injecting material and an electron transporting material, an organic material having an n-type property, that is, an organic material which is easily reduced and electrochemically stable at the time of reduction is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable state in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable. Accordingly, there is a need in the art to develop new organic materials having the above-described requirements.

One embodiment of the present invention provides novel organic electroluminescent compounds having appropriate energy levels, electrochemical stability, and thermal stability.

Another embodiment of the present invention provides an ink composition comprising the organic luminescent compound.

Another embodiment of the present invention provides an organic light emitting device comprising the organic light emitting compound.

Another embodiment of the present invention provides an electronic apparatus to which the organic light emitting device is applied.

In one embodiment of the present invention, there is provided an organic luminescent compound represented by the following general formula (1).

[Chemical Formula 1]

In this formula,

Each of R1, R2, R3 and R4 is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, And a substituted or unsubstituted C3 to C60 heteroaryl group, a substituted or unsubstituted C3 to C60 arylalkyl group, a substituted or unsubstituted C1 to C20 alkylamino group, a substituted or unsubstituted C6 to C60 arylamino group, A substituted C7 to C60 arylalkylamino group, a substituted or unsubstituted C7 to C60 arylalkoxyamino group,

L is a substituted or unsubstituted C6-C60 arylene group; A substituted or unsubstituted C3-C60 arylalkylene group; A substituted or unsubstituted C3 to C60 heteroarylene group; A substituted or unsubstituted C3 to C60 heteroarylalkylene group; And combinations thereof.

N is an integer of 0 to 1, and when n is 0, - (L) _n - is a single bond,

Het is a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C3 to C60 heteroaryl group,

The substituent when R 1, R 2, R 3 and R 4 and Het are substituted is selected from the group consisting of deuterium, a C 1 -C 50 alkyl group, a C 3 -C 50 cycloalkyl group, a C 2 -C 50 alkenyl group, a C 3 -C 50 cycloalkenyl group, A C5-C50 cycloalkynyl group, a cyano group, a C1-C20 alkoxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group, a C7-C60 arylalkyl group, .

In another embodiment of the present invention, there is provided an ink composition comprising at least one of the organic luminescent compounds.

According to another embodiment of the present invention, there is provided an organic light emitting device comprising a structure in which a first electrode, at least one organic material layer and a second electrode are stacked, and the organic material layer includes at least one organic light emitting compound.

In another embodiment of the present invention, there is provided an electronic device including the organic light emitting device.

The organic luminescent compound can satisfactorily satisfy the conditions required for a material usable in an organic light emitting device, for example, suitable energy level, electrochemical stability, and thermal stability. can do.

1 shows the 1H-NMR measurement results of the compound [20] prepared in the examples.
Fig. 2 is an enlarged graph of part of Fig.
Figure 3 is the UV absorption spectrum for the compound [20] prepared in the examples.
FIG. 4 is a graph showing a photoluminescence (PL) measurement graph for the compound [20] to be.
5 is a thermogravimetric analysis (TGA) graph for the compound [20] prepared in the Examples.
6 is a graph of differential scanning calorimetry (DSC) measurement for the compound [20] prepared in the examples.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

Unless defined otherwise, the term "substituted" in the present specification means a C1-C50 alkyl group, a C3-C50 cycloalkyl group, a C2-C50 alkenyl group, a C3-C50 cycloalkenyl group, a C2-C50 alkynyl group , A C5-C50 cycloalkynyl group, a cyano group, a C1-C20 alkoxy group, a C6-C60 aryl group, a C7-C60 arylalkyl group, and combinations thereof.

In the present specification, the term "combination thereof" means that two or more substituents are bonded to each other via a linking group or two or more substituents are condensed and bonded.

"는 동일하거나 상이한 원자 또는 화학식과 연결되는 부분을 의미한다.In the structural formula of the present specification,

Quot; means a moiety that is linked to the same or different atom or formula.

"Hetero" as used herein, unless otherwise defined, means containing a heteroatom in one compound or substituent, wherein the heteroatom is selected from the group consisting of N, O, S, P, Lt; / RTI > For example, it may mean one to three heteroatoms in the one compound or substituent, and the remainder is carbon.

In one embodiment of the present invention, there is provided a novel organic luminescent compound represented by the following general formula (1).

[Chemical Formula 1]

In this formula,

Each of R1, R2, R3 and R4 is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, And a substituted or unsubstituted C3 to C60 heteroaryl group, a substituted or unsubstituted C3 to C60 arylalkyl group, a substituted or unsubstituted C1 to C20 alkylamino group, a substituted or unsubstituted C6 to C60 arylamino group, A substituted C7 to C60 arylalkylamino group, a substituted or unsubstituted C7 to C60 arylalkoxyamino group,

L is a substituted or unsubstituted C6-C60 arylene group; A substituted or unsubstituted C3-C60 arylalkylene group; A substituted or unsubstituted C3 to C60 heteroarylene group; A substituted or unsubstituted C3 to C60 heteroarylalkylene group; And combinations thereof.

N is an integer of 0 to 1, and when n is 0, - (L) _n - is a single bond,

Het is a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C3 to C60 heteroaryl group,

The substituent when R 1, R 2, R 3 and R 4 and Het are substituted is selected from the group consisting of deuterium, a C 1 -C 50 alkyl group, a C 3 -C 50 cycloalkyl group, a C 2 -C 50 alkenyl group, a C 3 -C 50 cycloalkenyl group, A C5-C50 cycloalkynyl group, a cyano group, a C1-C20 alkoxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group, a C7-C60 arylalkyl group, .

Specifically, the Het is a substituted or unsubstituted six-membered ring containing 1 to 4 hetero atoms of nitrogen (N); Or a heteroaryl group of two to four fused or condensed rings of six-membered ring rings.

In one embodiment, the organic luminescent compound may be a compound represented by the following formula (2).

(2)

In Formula 2,

X, Y and Z are each independently carbon or nitrogen,

R5 and R6 are each independently selected from the group consisting of deuterium, a C1-C50 alkyl group, a C3-C50 cycloalkyl group, a C2-C50 alkenyl group, a C3-C50 cycloalkenyl group, a C2- An aryl group of C6-C60, a heteroaryl group of C3-C60, or an arylalkyl group of C7-C60,

R1, R2, R3, R4, L and n are as defined above.

More specifically, L may be any one of the following structures.

In the above structure,

Q is O, S, C = O, CH 2, C (CH 3) 2 or C (CF _{3) 2,}

또는

이고, 상기 n은 1 내지 10의 정수이다.
J is CH, CD, CF, CCN, COCH 3, CCH 3, CCH (CH 3) 2, CC (CH 3) 3, C (CH 2) n CH 3, CCF 3, N,

or

And n is an integer of 1 to 10.

For example, - (L) _n - can be specifically phenylene or naphthylene.

In another embodiment, it may be a compound represented by any one of the following formulas (3) to (6).

[Chemical Formula 3]

[Chemical Formula 5]

In the above Chemical Formulas 3 to 6,

Y, Z, R1, R2, R3, R4, R5, R6, L and n are as defined above.

For example, the organic luminescent compound may be any one of 1 to 100 described in Table 1 below.

The organic luminescent compound can be synthesized by, for example, reacting the following compound A, compound B, compound C, compound D, compound E, compound F and compound G according to the following reaction schemes 1 to 3.

Among the above-mentioned Compound A, Compound B, Compound C, Compound D, Compound E, Compound F and Compound G,

T, as T1, T2, T3, T4, T5, T6 and T7 are, each independently, Cl, Br, I, B (OH) _2,

또는

이고,

or

ego,

Het, R 1, R 2, R 3 and R 4 are as defined in the above formula (1).

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

In another embodiment of the present invention, there is provided an ink composition comprising at least one of the organic luminescent compounds.

The ink composition may be a solution or suspension comprising a solvent and the solvent is selected from the group consisting of anisole, dimethyl anisole, xylene, o-xylene, m-xylene, p-xylene, toluene, But are not limited to, tetrahydrofuran, tetrahydrofuran, methylene benzoate, dioxane, terahydrofuran, methyltetrahydrofuran, tetrahydropyrane, tetralin, veratrol, chlorobenzene, N-methylpyrrolidone, And a combination thereof.

The organic compound layer can be formed by applying the ink composition and removing the solvent to form a film.

The ink composition may further comprise a pigment or a dye.

The ink composition may further comprise a phosphorescent dopant or a fluorescent dopant.

According to another embodiment of the present invention, there is provided an organic light emitting device comprising a structure in which a first electrode, at least one organic material layer and a second electrode are stacked, and the organic material layer includes at least one organic light emitting compound.

The organic light emitting compound contained in the organic material layer of the organic light emitting device is a compound represented by the general formula (1), and a detailed description thereof is as described above.

The organic material layer may be produced by a known manufacturing method of forming or laminating an organic thin film layer, or the organic material layer may be prepared by a solution process using the ink composition as described above.

In one embodiment, the organic layer may include a light emitting layer, the light emitting layer may include the organic light emitting compound, and the organic light emitting compound may be included as a phosphorescent host, a fluorescent host, a phosphorescent dopant, or a fluorescent dopant material in the light emitting layer .

The light emitting layer may further include a phosphorescent host, a fluorescent host, a phosphorescent dopant, or a fluorescent dopant material of a known material, in addition to the compound represented by the general formula (1).

The organic material layer may suitably include at least one selected from the group consisting of a hole transporting layer, a hole injecting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer, and an electron blocking layer,

The hole transporting layer, the hole injecting layer, the hole blocking layer, the electron transporting layer, the electron injecting layer, and the electron blocking layer may each be formed using a known material or may include one or more organic electroluminescent compounds represented by Formula 1 .

In another embodiment of the present invention, there is provided an electronic device including the organic light emitting device.

The organic light emitting device can be applied to various applications. For example, the electronic device to which the organic light emitting device is applied may include an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O- ), An organic photovoltaic cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a luminescent electrochemical cell (LEC), an organic laser diode (OLED).

Hereinafter, examples and comparative examples of the present invention will be described. The following embodiments are only examples of the present invention, and the present invention is not limited to the following embodiments.

( Example )

Hereinafter, the reaction examples and the comparative examples are specifically exemplified, but the present invention is not limited to the following synthesis examples and examples. In the following reaction examples, the intermediate compounds are indicated by adding the serial number to the final product number. For example, Compound 1 is represented by the compound [1], and the intermediate compound of the above compound is represented by [1-1] or the like. In the present specification, the numbers of the compounds are represented by the numbers of the formulas shown in Table 1 above. For example, compounds designated 1 in Table 1 are designated Compound 1.

Synthetic example  1: Preparation of compound [20]

[Reaction Scheme 4]

Preparation of intermediate compound [20-1]

In a nitrogen atmosphere, 50 g (155.18 mmol) of 2-bromo-9-phenyl-9H-carbazole was dissolved in 400 ml of anhydrous tetrahydrofuran and cooled to -78 deg. After adding 74.4 ml (186.21 mmol) of 2.5M n-butyllithium at -78 ° C, the mixture was stirred at the same temperature for 20 minutes, and then 283.3 ml (201.73 mmol) of trimethyl borate was added thereto at that temperature and stirred for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, and 60 ml of 1N hydrochloric acid was added thereto. The mixture was stirred for 2 hours and then layered with dichloromethane / distilled water. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The concentrated solid was recrystallized from dichloromethane / hexane to obtain 29.9 g (68%) of the intermediate compound [20-1] .

Preparation of intermediate compound [20-2]

(56.03 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 19.3 g (67.23 mmol) of intermediate compound [20-1] and 11.6 g (84.04 mmol) of potassium carbonate in a nitrogen atmosphere, , 1.94 g (1.68 mmol) of tetrakis (triphenylphosphine) palladium, 450 ml of 1,4-dioxane and 45 ml of distilled water were added and stirred under reflux. When the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting solid was filtered and sufficiently washed with distilled water. The solid was washed with 200 ml of acetone and then with stirring. The filtered solid was recrystallized from dichloromethane / methanol to obtain 23.8 g (89%) of intermediate compound [20-2] .

Preparation of intermediate compound [20-3]

21 g (44.25 mmol) of the intermediate compound [20-2] was dissolved in 3 L of anhydrous tetrahydrofuran under nitrogen atmosphere, and 9.45 g (53.1 mmol) of N-bromosuccinimide was added thereto and stirred. When the reaction was complete, the resulting solid was washed with filtered methanol. The filtered solid was refluxed with stirring in 400 ml of methanol, cooled to room temperature and then filtered to obtain 23.9 g (98%) of intermediate compound [20-3] .

Preparation of compound [20]

Intermediate compounds in the atmosphere of nitrogen [20-3] 20g (36.13 mmol) , intermediate compound [20-4] 19.3g (43.36 mmol) , potassium carbonate 7.4g (54.19 mmol), tetrakis (triphenylphosphine) palladium, 1.25g (1.08 mmol), 1 L of 1,4-dioxane and 100 ml of distilled water were added, and the mixture was stirred under reflux. When the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting solid was filtered and sufficiently washed with distilled water. The solid was washed with 200 ml of acetone and then with stirring. The filtered solid was recrystallized using toluene to obtain 18.7 g (74%) of the objective compound [20] as a greenish yellow solid.

^{1 H NMR (400 MHz, CDCl} 3): δ 9.03 (s, 1H), 8.81 ~ 8.87 (m, 5H), 8.73 (s, 1H), 8.64 (s, 1H), 8.52 ~ 8.54 (d, 1H) (D, 1H), 7.80-7.87 (m, 5H), 7.54-7.71 (m, 14H), 7.43-7.45 (m, 2H), 7.30-7.31 t, 1 H)

MS / FAB: 715 (M ^< ^{+ &} gt ^; ).

1 is a ¹ H-NMR spectrum of the obtained compound [20].

Fig. 2 is a 1 H-NMR measurement result obtained by enlarging the region of about 7.2 to 9.2 ppm in Fig.

Fig. 3 is a UV absorption spectrum of the obtained compound [20].

FIG. 4 is a graph showing the photoluminescence (PL) measurement of the obtained compound [20] to be.

5 is a thermogravimetric analysis (TGA) graph for the obtained compound [20].

6 is a graph of differential scanning calorimetry (DSC) measurement for the compound [20] obtained above.

Synthetic example  2: Preparation of compound [53]

[Reaction Scheme 5]

Preparation of intermediate compound [53-1]

Synthesis Example 1 15 g (38.63 mmol) of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, 13.3 g (46.36 mmol) of intermediate compound [20-1] 18.1 g (85%) of Intermediate Compound [53-1] was synthesized by using 8.0 g (57.94 mmol) of potassium and 1.3 g (1.15 mmol) of tetrakis (triphenylphosphine) palladium.

Preparation of intermediate compound [53-2]

18.5 g (90%) of Intermediate Compound [53-2] was obtained by using 18 g (32.68 mmol) of Intermediate Compound [53-1] and 6.98 g (39.22 mmol) of N-bromosuccinimide in the same synthetic method as Synthesis Example 1, Were synthesized.

Preparation of intermediate compound [53-3]

Synthesis Example 1 53-3] was obtained by using 50 g (270.18 mmol) of 4-bromo-meta-xylene, 129.68 ml (324.21 mmol) of 2.5M n-butyllithium and 49.33 ml (351.23 mmol) 26.3g (65%) was synthesized.

Preparation of intermediate compound [53-4]

(121.98 mmol) of 4-bromo-2-iodo-1-nitrobenzene, 21.9 g (146.38 mmol) of intermediate compound [53-3] , 25.2 g (182.97 mmol) of potassium carbonate, Phenylphosphine) palladium (4.2 g, 3.65 mmol), 1,4-dioxane (600 ml) and distilled water (60 ml). When the reaction is completed, the reaction mixture is cooled to room temperature, and the organic layer is separated using ethyl acetate / distilled water, and then dried with anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and 26.1 g (70%) of intermediate compound [53-4] was synthesized by column chromatography.

Preparation of intermediate compound [53-5]

In a nitrogen atmosphere, 25 g (81.65 mmol) of the intermediate compound [53-4] , 42.5 ml (244.97 mmol) of triethylphosphite and 100 ml of isopropylbenzene were stirred under reflux. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The concentrate was separated and purified by column chromatography to obtain 19 g (85%) of intermediate compound [53-5] .

Preparation of intermediate compound [53-6]

(69.3 mmol) of intermediate compound [53-5] , 15.4 ml (138.6 mmol) of iodobenzene, 29.4 g (138.6 mmol) of potassium phosphate, 3.95 g (20.79 mmol) of copper iodide and 4.6 ml mmol) and 300 ml of toluene. After the reaction was completed, the reaction mixture was cooled to room temperature, and the organic layer was separated using ethyl acetate / distilled water, followed by drying with anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure, and 19.4 g (80%) of intermediate compound [53-6] was synthesized by column chromatography.

Preparation of intermediate compound [53-7]

Synthesis Example 1 Intermediate compounds synthesized in the same manner with the same synthetic method [53-6] 19g (54.24 mmol) , 2.5M n- butyllithium 26.1ml (65.09 mmol), trimethyl borate 9.9ml (70.51 mmol) of Intermediate Compound [53 - Use 7] (12.3 g, 72%).

Preparation of compound [53]

Synthesis Example 1 Intermediate compounds in the same synthesis method [53-2] 10g (15.88 mmol) , intermediate compound [53-7] 6.0g (19.06 mmol) , potassium carbonate 3.2g (23.82 mmol), tetrakis (triphenylphosphine) palladium 550mg (0.47 mmol) to obtain 9.37 g (72%) of the desired compound [53] as a greenish solid.

^{1 H NMR (400 MHz, CDCl} 3): δ 9.01 (s, 1H), 8.72 ~ 8.78 (m, 5H), 8.65 (s, 1H), 8.61 (s, 1H), 8.42 ~ 8.44 (d, 1H) , 8.21 (s, 3H), 2.34 (s, 3H), 8.21 (m, 2H)

MS / FAB: 819 (M ^< ^{+ &} gt ^; ).

Synthetic example  3-10

The compound [5], the compound [34], the compound [42], the compound [72], the compound [78], the compound [80], the compound [ [84] were synthesized.

Comparative Example  One

Wherein the compound represented by the following formula (a) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / Liq (30 nm) / a-NPD (30 nm) / ITO / 2-TNATA (1 nm) / Al (100 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, UV ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (a) and a compound represented by the formula (c) (doping ratio: 10 wt%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injection layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device. This is referred to as Comparative Sample 1.

Comparative Example  2

Wherein the compound represented by the following formula (b) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / Liq (30 nm) / a-NPD (30 nm) (1 nm) / Al (100 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, UV ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (b) and a compound represented by the formula (c) (doping ratio: 10 wt%) were vacuum-deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injection layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device. This is referred to as Comparative Sample 2.

<Formula a> <Formula b> <Formula c>

Example  1-5

In the same manner as in Comparative Example 1 except that phosphorescent green host (a) in Comparative Example 1 was used as a phosphorescent green host instead of Compound 20, 34, 42, 53 and 72 synthesized in Synthesis Example 1-5 (30 nm) / Alq ₃ (30 nm) / Liq (1 nm) / ITO / 2-TNATA (80 nm) /? -NPD (30 nm) / Compound 20, 34, 42, nm) / Al (100 nm). These are referred to as Samples 1 to 5, respectively.

Evaluation example  1: Evaluation of luminescence characteristics of Comparative Sample 1 and Samples 1 to 10

Comparative Example 1 and Samples 1 to 5 were evaluated for light emission luminance, light emission efficiency and emission peak using a Keithley source meter "2400" and a KONIKA MINOLTA "CS-2000", respectively, and the results are shown in Table 2 below. The samples showed green emission peak values in the range of 513-515 nm.

Sample No. Phosphorescent green host
No. Phosphorescent green dopant
No. Voltage
OP. V Luminance
[cd / m ² ] efficiency
[cd / A] Emission peak
[nm] Comparative Sample 1 a c 5.12 4759 47.59 514 Comparative Sample 2 b c 4.89 4652 46.52 513 One 20 c 4.31 5513 55.13 513 2 34 c 4.63 5629 56.29 513 3 42 c 4.53 5008 50.08 515 4 53 c 4.21 5516 55.16 515 5 72 c 4.58 5128 51.28 513

As shown in Table 2, Samples 1 to 5 exhibited improved luminescence characteristics as compared with Comparative Samples 1 and 2.

Evaluation example  2: Evaluation of life characteristics of Comparative Sample 1 and Samples 1 to 5

The comparative sample 1 and samples 1 to 5 were measured for time to reach 97% of life on the basis of 300 nits using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in Table 3 below .

Sample No. Phosphorescent green host
No. Phosphorescent green dopant
No. life span
Time [Hours] Comparative Sample 1 a c 45 Comparative Sample 2 b c 53 One 20 c 77 2 34 c 84 3 42 c 83 4 53 c 89 5 72 c 82

As shown in Table 3, Samples 1 to 5 exhibited improved life characteristics compared to Comparative Samples 1 and 2.

Comparative Example  3

(4,4 ', 4 "-tris (N-naphthalen-2- &lt; / RTI &gt; (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) /? - NPD (30 nm) / compound d + compound e (30 nm) Liq (1 nM) / Al (100 nM).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, UV ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (d) and a compound represented by the formula (e) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injecting layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in Table 3. This is referred to as Comparative Sample 3.

<Formula d> <Formula e>

Example  6 to 10

In Comparative Example 3, in the same manner as in Comparative Example 3, except that phosphorescent red host was used instead of phosphorescent red host d, the compounds represented by Formulas 5, 78, 80, 81 and 84 synthesized in the above Synthesis Example were used respectively (30 nm) / Alq ₃ (30 nm) / Liq (30 nm) / [Compound 5, 78, 80, 81, 84 + Compound e (10%)] ITO / 2-TNATA (1 nm) / Al (100 nm). These are referred to as Samples 6 to 10, respectively.

Evaluation example  3: Evaluation of luminescence characteristics of Comparative Sample 3 and Samples 6 to 10

Comparative Example 3 and Samples 6 to 10 were evaluated for light emission luminance, light emission efficiency and emission peak using a Keithley source meter "2400" and a KONIKA MINOLTA "CS-2000", respectively, and the results are shown in Table 4 below. The samples showed a red emission peak value in the range of 610 to 616 nm.

Sample No. Phosphorescent red host
No. Phosphorescent red dopant
No. Voltage
OP. V Luminance
[cd / m ² ] efficiency
[cd / A] Emission peak
[nm] Comparative Sample 3 d e 5.1 795 7.9 616 6 5 e 4.05 1662 16.62 614 7 78 e 4.24 1317 13.17 610 8 80 e 4.70 1295 12.95 611 9 81 e 4.34 1217 12.17 612 10 84 e 4.33 1157 11.57 613

As shown in Table 4, Samples 6 to 10 exhibited improved luminescence characteristics as compared with Comparative Sample 3.

Evaluation example  4: Evaluation of life characteristics of Comparative Sample 3 and Samples 6 to 10

Comparative Example 3 and samples 6 to 10 were measured for time to reach 97% of life on the basis of 5000 nits by using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in Table 5 below .

Sample No. Phosphorescent green host
No. Phosphorescent green dopant
No. life span
Time [Hours] Comparative Sample 3 d e 150 6 5 e 171 7 78 e 193 8 80 e 163 9 81 e 197 10 84 e 182

As shown in Table 5, Samples 6 to 10 showed improved lifetime characteristics as compared with Comparative Sample 3.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

Claims (19)

An organic light-emitting compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
Each of R1, R2, R3 and R4 is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, And a substituted or unsubstituted C3 to C60 heteroaryl group, a substituted or unsubstituted C3 to C60 arylalkyl group, a substituted or unsubstituted C1 to C20 alkylamino group, a substituted or unsubstituted C6 to C60 arylamino group, A substituted C7 to C60 arylalkylamino group, a substituted or unsubstituted C7 to C60 arylalkoxyamino group,
L is a substituted or unsubstituted C6-C60 arylene group; A substituted or unsubstituted C3-C60 arylalkylene group; A substituted or unsubstituted C3 to C60 heteroarylene group; A substituted or unsubstituted C3 to C60 heteroarylalkylene group; And combinations thereof.
N is an integer of 0 to 1, and when n is 0, - (L) _n - is a single bond,
Het is a substituted or unsubstituted 6-membered ring ring containing 1 to 4 hetero atoms of nitrogen (N); Or a fused or condensed ring of two to four of the six-membered ring rings; or a C3 to C60 heteroaryl group of
The substituent when R 1, R 2, R 3 and R 4 and Het are substituted is selected from the group consisting of deuterium, a C 1 -C 50 alkyl group, a C 3 -C 50 cycloalkyl group, a C 2 -C 50 alkenyl group, a C 3 -C 50 cycloalkenyl group, A C5-C50 cycloalkynyl group, a cyano group, a C1-C20 alkoxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group, a C7-C60 arylalkyl group, .
delete The method according to claim 1,
The organic luminescent compound is a compound represented by the following formula
Organic light emitting compounds:
(2)

In Formula 2,
Wherein X, Y and Z are each independently carbon or nitrogen, at least one of X, Y and Z is nitrogen,
R5 and R6 are each independently selected from the group consisting of deuterium, a C1-C50 alkyl group, a C3-C50 cycloalkyl group, a C2-C50 alkenyl group, a C3-C50 cycloalkenyl group, a C2- An aryl group of C6-C60, a heteroaryl group of C3-C60, or an arylalkyl group of C7-C60,
R1, R2, R3, R4, L and n are as defined in claim 1.
The method according to claim 1,
Wherein L is any one of the following structures
Organic light emitting compounds:

In the above structure,
Q is O, S, C = O, CH 2, C (CH 3) 2 or C (CF _{3) 2,}
J is CH, CD, CF, CCN, COCH 3, CCH 3, CCH (CH 3) 2, CC (CH 3) 3, C (CH 2) m CH 3, CCF 3, N,

or

And m is an integer of 1 to 10.
The method of claim 3,
A compound represented by any one of the following formulas (3) to
Organic light emitting compounds:
[Chemical Formula 3]

[Chemical Formula 5]

In the above Chemical Formulas 3 to 6,
Y and Z are each independently carbon or nitrogen,
R1, R2, R3, R4, L and n are as defined in claim 1,
R5 and R6 are each independently selected from the group consisting of deuterium, a C1-C50 alkyl group, a C3-C50 cycloalkyl group, a C2-C50 alkenyl group, a C3-C50 cycloalkenyl group, a C2-C50 alkynyl group, A cycloalkyl group, a cyano group, a C1-C20 alkoxy group, a C6-C60 aryl group, a C3-C60 heteroaryl group, or a C7-C60 arylalkyl group.
The method according to claim 1,
Wherein the organic luminescent compound is any one of the following compounds 1 to 100
Organic luminescent compound.

The method according to claim 1,
The organic luminescent compound is used as a material of an organic film for an organic light emitting device
Organic luminescent compound.
An ink composition comprising at least one organic luminescent compound according to any one of claims 1 to 7.
9. The method of claim 8,
The ink composition may be a solution or suspension further comprising a solvent,
Ink composition.
9. The method of claim 8,
The ink composition may further comprise a pigment or dye
Ink composition.
9. The method of claim 8,
Wherein the ink composition further comprises a phosphorescent dopant or a fluorescent dopant
Ink composition.
Wherein the first electrode, the organic layer including one or more organic layers, and the second electrode are stacked, and the organic layer includes at least one organic electroluminescent compound according to claim 1.
13. The method of claim 12,
Wherein the organic layer includes a light-emitting layer, and the light-emitting layer comprises at least one organic light-emitting compound according to claim 1
Organic light emitting device.
14. The method of claim 13,
The organic luminescent compound may be included in the luminescent layer as a phosphorescent host, a fluorescent host, a phosphorescent dopant, or a fluorescent dopant material
Organic light emitting device.
13. The method of claim 12,
Wherein the organic material layer includes at least one selected from the group consisting of a hole transporting layer, a hole injecting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer and an electron blocking layer
Organic light emitting device.
16. The method of claim 15,
Wherein the hole transport layer, the hole injection layer, the hole blocking layer, the electron transport layer, the electron injection layer, or the electron blocking layer comprises at least one organic electroluminescent compound according to claim 1
Organic light emitting device.
13. The method of claim 12,
Wherein the organic material layer is formed by applying an ink composition containing at least one organic electroluminescent compound according to claim 1 by a solution process,
Organic light emitting device.
An electronic device comprising the organic light-emitting device according to claim 12.
19. The method of claim 18,
The electronic device includes: an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O- ), An organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a luminescent electrochemical cell (LEC), an organic laser diode (O-
Electronics.

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