JP2012520872A - Novel organic electroluminescent compound and organic electroluminescent device using the same - Google Patents

Abstract

Novel organic electroluminescent compounds and organic electroluminescent devices comprising the same are disclosed. When used as a host material for an organic electroluminescent material in an OLED device, the disclosed organic electroluminescent compound exhibits high luminous efficiency and excellent lifetime characteristics of the material compared to conventional host materials. Thus it can be used to produce OLEDs with very good drive life.
[Representative] None

Description

  The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. Specifically, this invention relates to the novel organic electroluminescent compound used as an electroluminescent material, and the organic electroluminescent element which uses this as a host.

  The most important factor that determines the luminous efficiency of an OLED (organic light emitting diode) is the type of electroluminescent material. Although fluorescent materials have been widely used as electroluminescent materials, the development of phosphorescent materials is one of the best ways to theoretically improve luminous efficiency up to 4 times from the viewpoint of electroluminescent mechanism. .

To date, iridium (III) complexes are widely known as phosphorescent materials, for example, (acac) Ir (btp) ₂ , Ir (ppy) ₃ and Firepic are red, green and blue phosphorescent materials, respectively. Widely known. In particular, many phosphorescent materials have recently been developed in Japan, Europe and the United States.

  As the host material for phosphorescent materials, 4,4′-N, N′-dicarbazole-biphenyl (CBP) is the most widely known to date and hole blocking layers (eg, BCP and BAlq) are known. Applied high efficiency OLEDs are known. Pioneer (Japan) and others reported high performance OLEDs using bis (2-methyl-8-quinolinato) (p-phenylphenolato) aluminum (III) (BAlq) derivatives as hosts.

  Prior art materials are advantageous in terms of luminescent properties, but they have a low glass transition temperature and very poor thermal stability, so that the material is subjected to high temperature, vacuum deposition processes. Tend to change. In an OLED, power efficiency = (π / voltage) × current efficiency is defined. Thus, power efficiency is inversely proportional to voltage, and power efficiency should be higher to obtain lower power consumption of the OLED. In practice, OLEDs using phosphorescent electroluminescent materials exhibit significantly higher current efficiency (cd / A) than OLEDs using fluorescent EL materials. However, when conventional materials such as BAlq and CBP are used as host materials for phosphorescent materials, power efficiency (lm / w) due to higher drive voltage compared to OLEDs using fluorescent materials No significant advantage can be obtained from this point of view. Furthermore, such OLEDs cannot provide a satisfactory device lifetime.

  Therefore, there is a need for the development of host materials with improved stability and performance.

  The present inventor has sought to overcome the problems of the prior art, and as a result, invented a novel electroluminescent compound for realizing an organic electroluminescent device having excellent luminous efficiency and a significantly extended device lifetime.

  Thus, the object of the present invention is to overcome these problems and provide an organic electroluminescent compound comprising a skeleton that provides better luminous efficiency, improved device lifetime, and appropriate color coordinates compared to conventional host materials It is to be.

  Another object of the present invention is to provide a high-efficiency and long-life organic electroluminescent device using the organic electroluminescent compound as an electroluminescent material.

  Specifically, the present invention relates to an organic electroluminescent compound represented by any one of chemical formulas (1) to (5), and an organic electroluminescent device including the same. Since the organic electroluminescent compound of the present invention provides better luminous efficiency and superior lifetime characteristics compared to conventional host materials, an OLED having an excellent driving lifetime can be obtained from this compound.

Wherein, X and Y are independently N _(Ar 1), is selected from O and S, Ar ₁ may be different from each other, and Ar ₁ in the case where two or more Ar ₁ groups are present Ar Can be represented as ₁ or Ar ₂ ;
Z _{1 to} Z ₈ are independently selected from C (Ar ₃ ) and N, Ar ₃ may be different from each other, and adjacent Ar ₃ groups may be bonded together to form a ring. ;
Ar ₁ and Ar ₂ are independently 5- or 6-membered containing one or more heteroatoms selected from (C1-C60) alkyl, (C3-C60) cycloalkyl, N, O, S, Si and P Selected from heterocycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;
Ar ₃ is a 5-membered or independently containing one or more heteroatoms selected from hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, N, O, S, Si and P 6-membered heterocycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6-C60) Aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (C1-C60) alkylthio, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1 -C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl , Tri (C6-C30) arylsilyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C60) alkylboranyl, nitro and hydroxyl; and Ar ₁ -Ar ₃ alkyl; Cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylbora Nyl or alkylboranyl is a 5-membered containing one or more heteroatoms selected from (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, N, O, S, Si and P Or 6-membered heterocycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6-C60) ) Aryloxy, (C6-C60) aryl substituted with P (= O) R _a R _b [R _a and R _b independently represent (C1-C60) alkyl or (C6-C60) aryl], (C3-C60) heteroaryl, (C3-C60) heteroaryl substituted with (C6-C60) aryl, (C1-C60) heteroaryl substituted with (C1-C60) alkyl, (C6-C60) aryl (C1-C60) alkyl, (C6-C60) arylthio, (C1-C60) alkylthio, mono or (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryl May be further substituted with one or more substituents selected from the group consisting of silyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C60) alkylboranyl, nitro and hydroxyl;
However, the case where both X and Y are N (Ar ₁ ) and all of Z _{1 to} Z ₈ are C (Ar ₃ ) is excluded.

  As described herein, a substituent containing a “(C1-C60) alkyl” moiety contains 1 to 60 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms. Can do. Substituents containing a “(C 6 -C 60) aryl” moiety can contain 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. Substituents containing a “(C3-C60) heteroaryl” moiety can contain 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. Substituents containing a “(C 3 -C 60) cycloalkyl” moiety can contain 3 to 60 carbon atoms, 3 to 20 carbon atoms, or 3 to 7 carbon atoms. Substituents containing a “(C 2 -C 60) alkenyl or alkynyl” moiety can contain 2 to 60 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms.

  The term “alkyl” in the present invention includes linear or branched, saturated monovalent hydrocarbon groups or combinations thereof, which are composed solely of carbon and hydrogen atoms. The term “alkoxy” means an —O-alkyl group, where alkyl is defined as above.

  As used herein, the term “aryl” refers to an organic group derived from an aromatic hydrocarbon by removing one hydrogen atom from the aromatic hydrocarbon. Aryl groups include monocyclic or fused ring systems, each ring suitably containing 4 to 7, preferably 5 or 6 ring atoms. Also included are structures in which two or more aryl groups are brought together through chemical bonds. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrycenyl, naphthacenyl, fluoranthenyl and the like.

  As described herein, the term “heteroaryl” refers to 1 to 4 heteroatoms selected from N, O and S for an aromatic ring backbone atom and the remaining aromatic ring backbone atoms. An aryl group containing a carbon atom is meant. The heteroaryl may be a 5 or 6 membered monocyclic heteroaryl, or a polycyclic heteroaryl fused with one or more benzene rings, and may be partially saturated. Also included are structures having one or more heteroaryl groups linked through chemical bonds. A heteroaryl group can also include a divalent aryl group in which the heteroatom is oxidized or quaternized to form an N-oxide, quaternary salt, or the like. Specific examples include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, Pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, Benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolidinyl, quinoxalinyl, carbazolyl, phenane Lysinyl and benzodioxolyl; and their corresponding N- oxide (e.g., pyridyl N- oxide, quinolyl N- oxide), and quaternary salts include, but are not limited to.

式中、Ａｒ_１およびＡｒ_２は化学式（１）〜（５）におけるように定義される。 The organic electroluminescent compounds of the present invention may be exemplified by compounds represented by any of the following chemical formulas:

In the formula, Ar ₁ and Ar ₂ are defined as in chemical formulas (1) to (5).

式中、Ａｒ_１およびＡｒ_２は化学式（１）〜（５）におけるように定義される。 Furthermore, the organic electroluminescent compound of the present invention may be exemplified by a compound represented by any of the following chemical formulas:

In the formula, Ar ₁ and Ar ₂ are defined as in chemical formulas (1) to (5).

式中、Ａｒ_１は化学式（１）〜（５）におけるように定義される。 The organic electroluminescent compound of the present invention may be specifically exemplified by a compound represented by any of the following chemical formulas:

In the formula, Ar ₁ is defined as in chemical formulas (1) to (5).

More specifically, Ar ₁ and Ar ₂ independently represent phenyl, 1-naphthyl or 2-naphthyl, or a substituent represented by any of the following chemical formulas, but are not limited thereto:

  The present invention is an organic electroluminescent device comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, There is also provided an organic electroluminescent device in which the organic layer contains at least one organic electroluminescent compound represented by any one of chemical formulas (1) to (5).

  In the organic electroluminescent element of the present invention, the organic layer includes an electroluminescent layer, and the electroluminescent layer is one or more of compounds represented by any one of chemical formulas (1) to (5) as an electroluminescent host, and 1 Characterized by containing more than one phosphorescent dopant. This dopant is not particularly limited.

  The organic electroluminescent element of the present invention is selected from the group consisting of an arylamine compound and a styrylarylamine compound together with one or more organic electroluminescent compounds represented by any one of chemical formulas (1) to (5). More than one compound may be further included.

  In the organic electroluminescent element of the present invention, the organic layer has one or more organic electroluminescent compounds represented by any one of the chemical formulas (1) to (5), the first group, the second group, the fourth period, and It may further include one or more metals selected from the group consisting of a fifth periodic transition metal, a lanthanide metal and a d-transition element, or an organic metal of a complex thereof. The organic layer can include an electroluminescent layer and a charge generation layer.

  In order to form an organic electroluminescent element that emits white light, the organic electroluminescent element includes at least one organic electric field that emits blue, green, or red light in addition to the organic electroluminescent compound as described above. A light emitting layer can also be included.

  The organic electroluminescent compound of the present invention exhibits excellent luminous efficiency and very good lifetime characteristics of the material when used as a host material of an organic electroluminescent material of an OLED, resulting in very good driving from the compound OLEDs with a lifetime can be manufactured.

  In order to show the typical organic electroluminescent compounds of the present invention, their production, and the luminescent properties of electroluminescent devices, the present invention is further illustrated by reference to the production examples and examples, which are It is provided only for a better understanding of the embodiments of the invention and is not intended to limit the scope of the invention by any means.

Production Example [Production Example 1] Production of Compound (A)

Production of Compound (A-1) Bromo-2-nitrobenzene (30 g, 148.5 mmol), 1-naphthaleneboronic acid (30.6 g, 178.2 mmol), Pd (PPh ₃ ) ₄ (5.14 g, 4.45 mmol) ) A mixture of 2M aqueous K ₂ CO ₃ (297.01 mmol), toluene (500 mL) and ethanol (200 mL) was stirred at reflux for 4 hours. After the mixture was cooled to ambient temperature, distilled water was added thereto. The resulting mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (A-1) (31 g, 124.3 mmol, 84.03%).

Preparation of Compound (A-2) A mixture of compound (A-1) (31 g, 124.3 mmol) and triethyl phosphite (300 mL) was stirred under reflux for 10 hours. After cooling the mixture to ambient temperature, the organic solvent was distilled off under reduced pressure. Distilled water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (A-2) (18 g, 82.84 mmol, 66.81%).

Production of Compound (A-3) Compound (A-2) (18 g, 82.84 mmol), 1,5-diphenyl-3-chloropyridine (26.4 g, 99.41 mmol), Pd (OAc) ₂ (1. Reflux a mixture of 85 g, 8.28 mmol), P (t-bu) ₃ (8.17 ml, 16.5 mmol, 50% in xylene), NaOt-bu (23.8 g, 248.5 mmol) and toluene (500 mL). Stir for 12 hours. After the mixture was cooled to ambient temperature, distilled water was added to it and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (A-3) (19 g, 42.54 mmol, 51.36%).

Production of Compound (A-4) NBS (8.33 g, 46.80 mmol) was added to a solution of the compound (A-3) (19 g, 42.54 mmol) dissolved in DMF (200 mL). After 10 hours at ambient temperature, the organic solvent was distilled off under reduced pressure. Distilled water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (A-4) (20 g, 38.06 mmol, 89.47%).

Preparation of Compound (A-5) In a solution of Compound (A-4) (20 g, 38.06 mmol) dissolved in 200 mL of THF, n-buLi (15.22 mL, 38.06 mmol, 2.5 M in hexane) was −78. Slowly added at ° C. After stirring for 1 hour, trimethyl borate (5.51 mL, 49.48 mmol) was added thereto. The mixture was slowly warmed to ambient temperature and stirred for 12 hours. Distilled water was added and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (A-5) (8 g, 16.31 mmol, 42.86%).

Production of Compound (A-6) Compound (A-5) (8 g, 16.31 mmol), bromo-2-nitrobenzene (3.95 g, 19.57 mmol), Pd (PPh ₃ ) ₄ (0.56 g, 0.35 mmol). 48 mmol), a mixture of 2M aqueous K ₂ CO ₃ (16 mL, 32.62 mmol), toluene (70 mL), and ethanol (20 mL) was stirred under reflux. According to the same procedure as the synthesis of compound (A-1), compound (A-6) (7 g, 12.33 mmol, 75.62%) was obtained.

Production of Compound (A-7) Compound (A-6) (7 g, 12.33 mmol) was mixed with triethyl phosphite (100 mL), and the same procedure as the synthesis of compound (A-2) was performed to obtain compound (A A-7) (4 g, 7.46 mmol, 58.33%) was obtained.

Production of Compound (A) Compound (A-7) (4 g, 7.46 mmol), iodobenzene (1.25 mL, 11.20 mmol), copper powder (0.17 g, 11.20 mmol), K ₂ CO ₃ ( 3.09 g), 18-crown-6 (0.15 g, 1.59 mmol) and 1,2-dichlorobenzene (100 mL) were stirred under reflux for 15 hours. After cooling the reaction mixture to ambient temperature, the organic solvent was distilled off under reduced pressure. Distilled water was added thereto, and the mixture was extracted with ethyl acetate. The extract was purified through a column to obtain compound (A) (3.6 g, 5.88 mmol, 78.88%).

[Production Example 2] Production of compound (B)

Production of Compound (B-1) 1,4-Dibromo-2,3-dinitrobenzene (20 g, 61.36 mmol), 1-naphthaleneboronic acid (26 g, 153.42 mmol), Pd (PPh ₃ ) ₄ (3. 54 g, 3.06 mmol) A mixture of 2M aqueous K ₂ CO ₃ (90 mL), toluene (200 mL) and ethanol (100 mL) was stirred at reflux for 10 hours. After cooling the reaction mixture to ambient temperature, distilled water was added to it and the resulting mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (B-1) (22 g, 52.32 mmol, 85.28%).

Production of Compound (B-2) Compound (B-1) (22 g, 52.32 mmol) and triethyl phosphite (200 mL) were mixed and stirred at 180 ° C. According to the same procedure as the synthesis of compound (A-2), compound (B-2) (10 g, 28.05 mmol, 53.95%) was obtained.

Production of Compound (B-3) Compound (B-2) (10 g, 28.05 mmol), 2-iodonaphthalene (7.1 g, 28.05 mmol), copper powder (2.67 g, 42.08 mmol), K _A mixture of ₂ CO ₃ (11.63 g, 84.17 mmol), 18-crown-6 (0.59 g, 2.24 mmol) and 1,2-dichlorobenzene (100 mL) was stirred at 190 ° C. for 20 hours. After cooling to ambient temperature, the organic solvent was distilled off under reduced pressure. Distilled water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (B-3) (4 g, 8.28 mmol, 29.60%).

Preparation of Compound (B) Compound dissolved in DMF (20 mL) in a reaction vessel containing NaH (0.49 g, 12.43 mmol, 60% dispersion in mineral oil) dissolved in DMF (20 mL) A solution of (B-3) (4 g, 8.28 mmol) was added. After 1 hour, to this was added a solution of 2-chloro-4,6-diphenyltriazine (2.66 g, 9.94 mmol) dissolved in DMF (20 mL). After stirring for 12 hours, distilled water was added and the resulting solid was filtered off under reduced pressure. Recrystallization from ethyl acetate and DMF gave compound (B) (3.5 g, 4.90 mmol, 59.21%).

[Production Example 3] Production of compound (C)

Preparation of Compound (C-1) 2-Naphthylhydrazine (20 g, 126.42 mmol) was slowly added to a solution of 1,2-cyclohexyldione (42.52 g, 379.26 mmol) dissolved in ethanol (1000 mL). did. To this was added acetic acid (0.28 mL, 5.05 mmol) and the mixture was heated to 40 ° C. After 2 hours, the mixture was cooled and distilled water was added thereto. The resulting solid was filtered off under reduced pressure to obtain compound (C-1) (17 g, 67.37 mmol, 53.47%).

Preparation of Compound (C-2) To compound (C-1) (17 g, 67.37 mmol) dissolved in acetic acid (100 mL) was added trifluoroacetic acid (10 mL). After stirring for 2 hours at ambient temperature, distilled water was added thereto. The mixture was neutralized with aqueous NaOH and extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (C-2) (11 g, 46.75 mmol, 69.39%).

Production of Compound (C-3) According to the same procedure as the synthesis of Compound (B-3), Compound (C-3) (10 g, 32.11 mmol, 68.69%) was obtained.

Production of Compound (C-4) According to the same procedure as the synthesis of Compound (C-1), Compound (C-4) (12 g, 29.88 mmol, 93.07%) was obtained.

Preparation of Compound (C-5) According to the same procedure as the synthesis of Compound (C-2), Compound (C-5) (6 g, 15.68 mmol, 52.50%) was obtained.

Production of Compound (C) According to the same procedure as the synthesis of compound (B), compound (C) (5 g, 8.14 mmol, 51.95%) was obtained.

[Production Example 4] Production of compound (D)

Production of Compound (D-2) Following the same procedure as the synthesis of Compound (A-1), but using Compound (D-1), Compound (D-2) (11 g, 38.02 mmol, 89.22%) was obtained. Obtained.

Production of Compound (D-3) According to the same procedure as the synthesis of compound (A-2), compound (D-3) (8 g, 31.09 mmol, 81.78%) was obtained.

Preparation of compound (D) According to the same procedure as the synthesis of compound (B), compound (D) (6 g, 12.30 mmol, 38.70%) was obtained.

[Production Example 5] Production of compounds E and F

Production of Compound (E-2) Following the same procedure as the synthesis of Compound (A-1), but using Compound (E-1), Compound (E-2) (15 g, 51.85 mmol, 86.51%) was prepared. Obtained.

Production of Compound (E-3) According to the same procedure as the synthesis of compound (A-2), compound (E-3) (6 g, 23.31 mmol, 44.97%) was obtained.

Production of Compound (E) According to the same procedure as the synthesis of compound (B), compound (E) (5 g, 10.25 mmol, 43.99%) was obtained.

Production of Compound (F-1) According to the same procedure as the synthesis of Compound (A-2), Compound (F-1) (3 g, 11.65 mmol, 22.48%) was obtained.

Production of Compound (F) According to the same procedure as the synthesis of compound (B), compound (F) (3 g, 6.15 mmol, 52.81%) was obtained.

[Production Example 6] Production of compounds (G) and (H)

Production of Compound (G-1) Carbazole (20 g, 119.6 mmol), iodobenzene (20 mL, 179.41 mmol), copper (11.4 g, 179.41 mmol), K ₂ CO ₃ (49 g, 358.8 mmol), A mixture of 18-crown-6 (2.5 g, 9.56 mmol) and 1,2-dichlorobenzene was stirred at 190 ° C. for 12 hours. After cooling to ambient temperature, the reaction mixture was distilled under reduced pressure. Distilled water was added thereto, and the resulting mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled under reduced pressure. Purification through a column gave compound (G-1) (22 g, 90.42 mmol, 75.60%).

Production of Compound (G-2) According to the same procedure as the synthesis of Compound (A-4), Compound (G-2) (25 g, 77.59 mmol, 85.81%) was obtained.

Production of Compound (G-3) According to the same procedure as the synthesis of compound (A-5), compound (G-3) (11 g, 38.31 mmol, 49.37%) was obtained.

Production of Compound (G-4) According to the same procedure as the synthesis of compound (A-1), compound (G-4) (12 g, 32.84 mmol, 85.72%) was obtained.

Production of Compound (G-5) According to the same procedure as the synthesis of Compound (A-2), the reaction was performed for 4 hours to obtain Compound (G-5) (6 g, 17.99 mmol, 54.80%). .

Production of Compound (G) According to the same procedure as the synthesis of compound (B), compound (G) (7 g, 12.39 mmol, 68.91%) was obtained.

Production of Compound (H-1) According to the same procedure as the synthesis of Compound (A-2), the reaction was performed for 4 hours to obtain Compound (H-1) (2 g, 5.99 mmol, 18.26%).

Production of Compound (H) According to the same procedure as the synthesis of compound (B), compound (H) (1.7 g, 3.01 mmol, 50.26%) was obtained.

Organic electroluminescent compounds (TA, TB and TC) were produced according to the procedures of Production Examples 1-6. Tables 1 and 2 show the substituents (Ar ₁ , Ar ₂ ) of these organic electroluminescent compounds prepared in this way, and ¹ H NMR and MS / FAB data of these compounds.

[Examples 1 to 10]
Production of OLED using organic electroluminescent compound of the present invention An OLED element was produced by using the electroluminescent compound of the present invention.
First, the transparent electrode ITO thin film (15Ω / □) prepared from the glass for OLED (manufactured by Samsung-Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water in order, and stored in isopropanol. Then used.
Next, an ITO substrate is attached to the substrate holder of the vacuum deposition apparatus, and 4,4 ′, 4 ″ -tris (N, N- (2-naphthyl) -phenylamino) triphenylamine ( 2-TNATA) (this chemical structure is shown below) and then vented the chamber to a vacuum of 10 ⁻⁶ torr, applying an electric current to the cell to evaporate 2-TNATA, Produced a deposit of a hole injection layer having a thickness of 60 nm on the ITO substrate.

  Next, N, N′-bis (α-naphthyl) -N, N′-diphenyl-4,4′-diamine (NPB) is placed in another cell of the vacuum evaporation apparatus, and current is applied to this cell. NPB was evaporated, thereby producing a 20 nm thick hole transport layer deposit on the hole injection layer.

The compound of the present invention (for example, compound TA8-H4-H2) purified by vacuum sublimation at 10 ⁻⁶ torr is applied to one cell of the vacuum deposition apparatus, and the electroluminescent dopant (for example, compound to the other cell). (Piq) ₂ Ir (acac)) was added. The two materials were evaporated at different rates and doped at a concentration of 4-10 mol%, thereby depositing an electroluminescent layer having a thickness of 30 nm on the hole transport layer.

  Next, tris (8-hydroxyquinoline) aluminum (III) (Alq) (this structure is shown below) is deposited as an electron transport layer in a thickness of 20 nm, and lithium quinolate (Liq) is used as an electron injection layer. Vapor deposition was performed with a thickness of 1 to 2 nm. Thereafter, an Al cathode having a thickness of 150 nm was vapor-deposited using another vacuum vapor deposition apparatus to produce an OLED.

[Examples 11 to 20]
Preparation of OLEDs by using the electroluminescent compounds of the invention The same procedure is followed as for the OLEDs of Examples 1-10, but using the compounds of the invention (e.g. compounds TA4-H4-H4) as host material, An OLED was manufactured using an organic iridium complex (Ir (ppy) ₃ ) represented by the following chemical formula as an electroluminescent dopant.
Each material used to manufacture the OLED was used as an electroluminescent material after being purified by vacuum sublimation at 10 ⁻⁶ torr.

[Comparative Examples 1 and 2]
Production of OLEDs by using conventional electroluminescent materials The same procedure as described in Examples 1 and 11 is followed, but in the other cell of the vacuum deposition apparatus, instead of the electroluminescent compound of the invention as a host material. Bis (2-methyl-8-quinolinato) (p-phenylphenolato) aluminum (III) (BAlq) was added to produce an OLED.

OLEDs made from Examples 1-10 and Examples 11-20 (which contain the organic electroluminescent compounds of the present invention), and OLEDs made from Comparative Examples 1 and 2 (these are conventional electroluminescent compounds) Drive voltage and power efficiency were measured at 1,000 cd / m ² and the results are shown in Tables 3 and 4.

  As can be seen from Tables 3 and 4, the organic electroluminescent compound developed according to the present invention exhibited superior characteristics compared to conventional materials in terms of device performance.

  As can be seen from Table 3, the compounds developed according to the present invention exhibited superior properties in terms of luminescent properties compared to conventional materials. The device manufactured according to the present invention exhibited excellent current characteristics as compared with the device of Comparative Example 1 manufactured using a conventional material, thereby providing a driving voltage lower by 1V or more. They also exhibited current efficiency characteristics that were at least 1.4 times higher than the device of Comparative Example 1 due to significantly improved emission characteristics.

As can be seen from Table 4, when the compound developed according to the present invention is used as a host for green electroluminescence, this device is superior to the device of Comparative Example 2 because of its excellent emission characteristics. It showed a fairly high power efficiency of at least 1.6 times. Excellent light emission characteristics were confirmed in comparison with conventional materials. In particular, the device of Example 14 is driven at a voltage 2.7 V lower than that of the device of Comparative Example 1, and the device of Example 17 has a power efficiency of 15.9 lm / W at 1000 cd / m ² and 5.5 V. The driving voltage is shown.

  Therefore, an element using the electroluminescent compound according to the present invention as a host material for emitting red or green light exhibits excellent emission characteristics and lowers the driving voltage, and as a result, particularly for emitting green light. The device induces an increase in output efficiency of 5.1-7.7 lm / W, resulting in improved power consumption.

Claims (10)

Organic electroluminescent compound represented by any one of chemical formulas 1 to 5:

Wherein, X and Y are independently N _(Ar 1), is selected from O and S, Ar ₁ may be different from each other, and Ar ₁ in the case where two or more Ar ₁ groups are present Ar Can be represented as ₁ or Ar ₂ ;
Z _{1 to} Z ₈ are independently selected from C (Ar ₃ ) and N, Ar ₃ may be different from each other, and adjacent Ar ₃ groups may be bonded together to form a ring. ;
Ar ₁ and Ar ₂ are independently 5- or 6-membered containing one or more heteroatoms selected from (C1-C60) alkyl, (C3-C60) cycloalkyl, N, O, S, Si and P Selected from heterocycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;
Ar ₃ is a 5-membered or independently containing one or more heteroatoms selected from hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, N, O, S, Si and P 6-membered heterocycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6-C60) Aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (C1-C60) alkylthio, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1 -C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl , Tri (C6-C30) arylsilyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C60) alkylboranyl, nitro and hydroxyl; and Ar ₁ -Ar ₃ alkyl; Cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylbora Nyl or alkylboranyl is a 5-membered containing one or more heteroatoms selected from (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, N, O, S, Si and P Or 6-membered heterocycloalkyl, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6-C60) ) Aryloxy, (C6-C60) aryl substituted with P (= O) R _a R _b [R _a and R _b independently represent (C1-C60) alkyl or (C6-C60) aryl], (C3-C60) heteroaryl, (C3-C60) heteroaryl substituted with (C6-C60) aryl, (C1-C60) heteroaryl substituted with (C1-C60) alkyl, (C6-C60) aryl (C1-C60) alkyl, (C6-C60) arylthio, (C1-C60) alkylthio, mono or (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryl May be further substituted with one or more substituents selected from the group consisting of silyl, mono or di (C6-C30) arylboranyl, mono or di (C1-C60) alkylboranyl, nitro and hydroxyl;
However, the case where both X and Y are N (Ar ₁ ) and all of Z _{1 to} Z ₈ are C (Ar ₃ ) is excluded. The organic electroluminescent compound of claim 1 selected from the following compounds:

Wherein Ar ₁ and Ar ₂ are defined as in claim 1. The organic electroluminescent compound of claim 1 selected from the following compounds:

Wherein Ar ₁ and Ar ₂ are defined as in claim 1. The organic electroluminescent compound of claim 1 selected from the following compounds:

Wherein Ar ₁ is defined as in claim 1.   The organic electroluminescent element containing the organic electroluminescent compound of any one of Claims 1-4.   An organic electroluminescent device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein the organic layer is claimed. The organic electroluminescent element of Claim 5 containing 1 or more types of the organic electroluminescent compound of any one of 1-4, and 1 or more types of phosphorescence dopants.   The organic electroluminescent element according to claim 6, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds.   The organic layer is one selected from the group consisting of Group 1, Group 2, Group 4 and Group 5 transition metals, lanthanide metals and d-transition elements, or complex organometallics formed therefrom. The organic electroluminescent element according to claim 6, further comprising the above metal.   The organic electroluminescent element according to claim 6, wherein the organic layer includes an electroluminescent layer and a charge generation layer.   The organic electroluminescence device according to claim 6, wherein the organic electroluminescence device is an organic electroluminescence device that emits white light, and the organic layer simultaneously includes one or more organic electroluminescence layers that emit blue, red, or green light. element.