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CN105001224A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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Publication number
CN105001224A
CN105001224A CN201510340976.8A CN201510340976A CN105001224A CN 105001224 A CN105001224 A CN 105001224A CN 201510340976 A CN201510340976 A CN 201510340976A CN 105001224 A CN105001224 A CN 105001224A
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organic electroluminescent
compound
organic
aryl
heteroaryl
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Inventor
金侈植
赵英俊
权赫柱
金奉玉
金圣珉
尹胜洙
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Rohm and Haas Electronic Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

Disclosed are a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. When used as host material of organic electroluminescent material of an OLED device, the disclosed organic electroluminescent compound exhibits high luminous efficiency and excellent life property of the material as compared to conventional host material. Therefore, it can be used to manufacture OLEDs having very good operation life.

Description

Novel organic electroluminescent compounds and organic electroluminescent device using the same
The present invention patent application is a divisional application of an invention patent application having an application number of 201310559945.2 and an application date of 2010, 3.17.3 entitled "novel organic electroluminescent compound and organic electroluminescent device using the same". And the above-mentioned invention patent application is divisional application of the invention patent application with international application number PCT/KR2010/001647, international application date 2010, 3.17.2010, application number 201080022499.6 in the phase of chinese country, entitled "new organic electroluminescent compound and organic electroluminescent device using the same".
Technical Field
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. More particularly, the present invention relates to novel organic electroluminescent compounds useful as electroluminescent materials, and organic electroluminescent devices using them as hosts (host).
Background
The most important factor determining the luminous efficiency of an OLED (organic electroluminescent diode) is the type of electroluminescent material. Although fluorescent materials have been widely used as electroluminescent materials so far, the development of phosphorescent materials is one of the best methods to theoretically improve the luminous efficiency up to 4 times from the viewpoint of the electroluminescent mechanism.
Up to now, iridium (III) complexes are well known as phosphorescent materials, including (acac) Ir (btp)2、Ir(ppy)3And Firpic as red, green and blue phosphorescent materials, respectively.In particular, many phosphorescent materials have been currently studied in japan, europe, and the united states.
As a host material of a phosphorescent light emitting material, 4'-N, N' -dicarbazole-biphenyl (CBP) is most widely known so far, and an OLED having high efficiency using a hole blocking layer (e.g., BCP and BAlq) is known. Pioneer (japan) has reported high performance OLEDs using bis (2-methyl-8-quinolinolato) (p-phenylphenolato) aluminum (III) (BAlq) derivatives as the matrix.
Although the prior art materials are advantageous in view of luminescence properties, they have a low glass transition temperature and very poor thermal stability, so that these materials tend to change at high temperatures and under vacuum during the vapor deposition process. In the OLED, power efficiency is defined as (pi/voltage) × current efficiency. Therefore, power efficiency is inversely proportional to voltage, and power efficiency should be higher to get lower OLED power consumption. In practice, OLEDs using phosphorescent electroluminescent materials show significantly higher current efficiencies (cd/a) than OLEDs using fluorescent EL materials. However, in the case of using conventional materials such as BAlq and CBP as a host material for a phosphorescent material, there is no significant advantage in power efficiency (lm/w) because of a higher operating voltage compared to an OLED using a fluorescent material. Moreover, the OLED cannot obtain a satisfactory device life.
Therefore, development of a matrix material with further improved stability and performance is required.
Disclosure of Invention
Description of the invention technical problem
The present inventors have endeavored to overcome the problems of the conventional art to invent novel electroluminescent compounds to realize an organic electroluminescent device having excellent luminous efficiency and significantly prolonged device lifetime.
It is therefore an object of the present invention to overcome the above problems and to provide organic electroluminescent compounds comprising a skeleton to achieve higher luminous efficiency, improved device lifetime and suitable color coordinates compared to conventional host materials.
It is another object of the present invention to provide an organic electroluminescent device having high efficiency and long life using the organic electroluminescent compound as an electroluminescent material.
Means for solving the problems
Specifically, the present invention relates to an organic electroluminescent compound represented by one of chemical formulas (1) to (5) and an organic electroluminescent device including the same. Since the organic electroluminescent compounds according to the invention provide better luminous efficiency and excellent life property compared to conventional host materials, OLEDs having excellent operation life can be obtained.
[ chemical formula 1]
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
Wherein,
x and Y are independently selected from N (Ar)1) O and S, wherein Ar1May be different from each other and have two or more Ar1When radical, Ar1Can be represented as Ar1Or Ar2；
Z1To Z8Independently selected from C (Ar)3) And N, wherein Ar3Can be different from each other and adjacent Ar3The groups may be linked together to form a ring;
Ar1and Ar2Independently selected from (Cl-C60) alkyl, (C3-C60) cycloalkyl, 5-or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S, Si and P, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl;
Ar3independently selected from hydrogen, (Cl-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5-or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S, Si and P, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxy, (C6-C60) aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (Cl-C60) alkylthio, mono-or di (Cl-C30) alkylamino, mono-or di (C6-C30) arylamino, tri (Cl-C30) alkylsilyl, di (Cl-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, mono-or di (C6-C30) arylboryl, mono-or di (Cl-C60) alkylboryl, nitro and hydroxy; and
Ar1to Ar3The alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, arylboryl or alkylboryl of (a) may be further substituted with one or more substituents selected from the group consisting of: (Cl-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5-or 6-membered heterocycloalkyl containing one or more heteroatoms selected from N, O, S, Si and P, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-C60) alkoxy, (C6-C60) aryloxy, P (═ O) RaRb[RaAnd RbIndependently represent (Cl-C60) alkyl or (C6-C60) aryl]Substituted (C6-C60) aryl, (C3-C60) heteroaryl, (C6-C60) aryl-substituted (C3-C60) heteroaryl, (Cl-C60) alkyl-substituted (C3-C60) heteroaryl, (C6-C60) aryl (Cl-C60) alkyl, (C6-C60) arylthio, (Cl-C60) alkylthio, mono-or di (Cl-C30) alkylamino, mono-or di (C6-C30) arylamino, tri (Cl-C30) alkylsilyl, di (Cl-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, mono-or di (C6-C30) arylboryl, mono-or di (Cl-C60) alkylboryl, nitro and hydroxy, excluding such cases: x and Y are both N (Ar)1) And Z is1To Z8Are all C (Ar)3)。
Substituents described herein that include "(Cl-C60) alkyl" moieties can contain 1-60 carbon atoms, 1-20 carbon atoms, or 1-10 carbon atoms. Substituents comprising "(C6-C60) aryl" moieties may contain 6-60 carbon atoms, 6-20 carbon atoms, or 6-12 carbon atoms. Substituents comprising a "(C3-C60) heteroaryl" moiety may contain 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. Substituents comprising a "(C3-C60) cycloalkyl" moiety may contain 3-60 carbon atoms, 3-20 carbon atoms, or 3-7 carbon atoms. Substituents comprising "(C2-C60) alkenyl or alkynyl" moieties may contain 2-60 carbon atoms, 2-20 carbon atoms, or 2-10 carbon atoms.
The term "alkyl" in the present invention includes straight or branched chain saturated monovalent hydrocarbon groups or combinations thereof, which may consist of only carbon and hydrogen atoms. The term "alkoxy" denotes an-O-alkyl group, wherein alkyl is as defined above.
The term "aryl" as used herein refers to an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen atom. Aryl includes monocyclic or fused ring systems, each ring of the aryl suitably containing from 4 to 7, preferably from 5 to 6, ring atoms. It may also include a structure in which two or more aryl groups are bonded by a chemical bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, benzo [9,10 ] benzo]Phenanthryl (triphenylenyl), pyrenyl, perylenyl, perylene, and mixtures thereof,A chrysenyl group, a naphthacenyl group, a fluoranthenyl group, and the like, but not limited thereto.
The term "heteroaryl" as used herein means an aryl group containing 1 to 4 heteroatoms selected from N, O and S in the aromatic ring backbone atoms with the remaining aromatic ring backbone atoms being carbon atoms. The heteroaryl group may be a 5-or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group fused to one or more phenyl rings, and may be partially saturated. Structures having one or more heteroaryl groups attached by chemical bonds are also included. The heteroaryl group can include divalent aryl groups whose heteroatoms are oxidized or quaternized to form N-oxides, quaternary ammonium salts, and the like. Specific examples include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolylAzolyl group,Azolyl group,Oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groupsFor example benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolylAzolyl, benzoAzolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl (cinnolinyl), quinazolinyl, quinolizinyl (quinoxalinyl), quinoxalinyl (quinoxalinyl), carbazolyl, phenanthridinyl (phenanthridinyl), benzodioxolyl (benzodioxolyl); and their corresponding N-oxides (e.g., pyridyl N-oxide, quinolyl N-oxide); and quaternary ammonium salts thereof, but are not limited thereto.
Examples of the organic electroluminescent compounds according to the present invention may be compounds represented by one of the following chemical formulas:
wherein: ar (Ar)1And Ar2As defined in chemical formulas (1) to (5).
In addition, examples of the organic electroluminescent compounds of the present invention may be compounds represented by one of the following chemical formulas:
wherein: ar (Ar)1And Ar2As defined in chemical formulas (1) to (5).
Specific examples of the organic electroluminescent compounds according to the present invention may be compounds represented by one of the following chemical formulas:
wherein: ar (Ar)1And Ar2As defined in chemical formulas (1) to (5).
More specifically, Ar1And Ar2Independently represents a phenyl group, a 1-naphthyl group or a 2-naphthyl group or a substituent represented by one of the following chemical formulae, but they are not limited thereto.
The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode; wherein the organic layer includes one or more organic electroluminescent compounds represented by one of chemical formulas (1) to (5).
The organic electroluminescent device of the present invention is characterized in that the organic layer comprises an electroluminescent layer comprising one or more compounds represented by one of chemical formulas (1) to (5) as an electroluminescent host and one or more phosphorescent dopants. The dopant is not particularly limited.
The organic electroluminescent device of the present invention may further comprise one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds, and one or more organic electroluminescent compounds represented by one of chemical formulas (1) to (5).
In the organic electroluminescent device of the present invention, the organic layer may further include one or more metals selected from transition metals of group 1, group 2, fourth and fifth periods of the periodic table, lanthanoid metals and D-transition elements, or complexes thereof, and one or more organic electroluminescent compounds represented by one of chemical formulas (1) to (5). The organic layer may include an electroluminescent layer and a charge generation layer.
In addition to the above organic electroluminescent compounds, the organic electroluminescent device may also include one or more organic electroluminescent layers emitting blue, green or red light to form an organic electroluminescent device emitting white light.
Advantageous effects of the invention
The organic electroluminescent compounds according to the present invention show excellent luminous efficiency and excellent life property when used as a host material for an organic electroluminescent material of an OLED, so that an OLED having very good operation life can be manufactured therefrom.
Modes for carrying out the invention
The present invention is further described by referring to preparation examples and examples to illustrate representative organic electroluminescent compounds of the present invention, a method for preparing the same, and light emitting properties of electroluminescent devices, but these examples are provided only for better understanding of embodiments of the present invention and are not intended to limit the scope of the present invention in any way.
Preparation example
Preparation example 1: preparation of Compound (A)
Preparation of Compound (A-1)
Bromo-2-nitrobenzene (30g,148.5mmol), 1-naphthalene boronic acid (1-naphthalene boronic acid) (30.6g,178.2mmol), Pd (PPh)3)4(5.14g,4.45mmol),2M K2CO3A mixture of aqueous solution (297.01mmol), toluene (500mL) and ethanol (200mL) was stirred under reflux for 4 hours. After the mixture was cooled to room 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 by column gave compound (A-1) (31g,124.3mmol, 84.03%).
Preparation of Compound (A-2)
A mixture of compound (A-1) (31g,124.3mmol) and triethyl phosphite (300mL) was stirred at reflux for 10 hours. After the mixture was cooled to room 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 by column gave compound (A-2) (18g,82.84mmol, 66.81%).
Preparation of Compound (A-3)
Compound (A-2) (18g,82.84mmol), l, 5-diphenyl-3-chloropyridine (26.4g,99.41mmol), Pd (OAc)2(1.85g,8.28mmol),P(t-bu)3(8.17mL,16.5mmol, 50% in xylene), a mixture of NaOt-bu (23.8g,248.5mmol) and toluene (500mL) was stirred at reflux for 12 h. After the mixture was cooled to room temperature, 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 by column gave compound (A-3) (19g,42.54mmol, 51.36%).
Preparation of Compound (A-4)
To a solution of compound (A-3) (19g,42.54mmol) in DMF (200mL) was added NBS (8.33g,46.80 mmol). After standing at room temperature for 10 hours, 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 by column gave compound (A-4) (20g,38.06mmol, 89.47%).
Preparation of Compound (A-5)
To a solution of compound (A-4) in THF (200mL) at-78 deg.C was added n-buLi (15.22mL,38.06mmol, 2.5M in hexanes) slowly. After stirring for 1 hour, trimethyl borate was added thereto. The mixture was slowly warmed to room temperature and stirred for 12 hours. 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 by column gave compound (A-5) (8g,16.31mmol, 42.86%).
Preparation of Compound (A-6)
Compound (A-5) (8g,16.31mmol), bromo-2-nitrobenzene (3.95g,19.57mmol), Pd (PPh)3)4(0.56g,0.48mmol),2M K2CO3A mixture of aqueous solution (16mL,32.62mmol), toluene (70mL) and ethanol (20mL) was stirred at reflux. Compound (A-6) (7g,12.33mmol, 75.62%) was obtained according to the same procedure as that for the synthesis of Compound (A-1).
Preparation of Compound (A-7)
Compound (A-6) (7g,12.33mmol) was mixed with triethyl phosphite (100mL), and compound (A-7) (4g,7.46mmol, 58.33%) was obtained according to the same procedure as that for the synthesis of compound (A-2).
Preparation of Compound (A)
Compound (A-7) (4g,7.46mmol), iodobenzene (1.25mL,11.20mmol), copper powder (0.71g,11.20mmol), K2CO3A mixture of (3.09g), 18-crown-6 (0.15g,0.59mmol) and 1, 2-dichlorobenzene (100mL) was stirred at reflux for 15 hours. After the reaction mixture was cooled to room 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 by column to give compound (A) (3.6g,5.88mmol, 78.88%).
Preparation example 2: preparation of Compound (B)
Preparation of Compound (B-1)
l, 4-dibromo-2, 3-dinitrobenzene (20g,61.36mmol), 1-naphthalene boronic acid (26g,153.42mmol), Pd (PPh)3)4(3.54g,3.06mmol),2M K2CO3A mixture of aqueous solution (90mmol), toluene (200mL) and ethanol (100mL) was stirred under reflux for 10 h. After the reaction mixture was cooled to room temperature, 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 by column gave compound (B-1) (22g,52.32mmol, 85.28%).
Preparation of Compound (B-2)
Compound (B-1) (22g,52.32mmol) and triethyl phosphite (200mL) were mixed and stirred at 180 ℃. Compound (B-2) (10g,28.05mmol, 53.95%) was obtained according to the same procedure as that for the synthesis of Compound (A-2).
Preparation of Compound (B-3)
Compound (B-2) (10g,28.05mmol), 2-iodonaphthalene (7.1g, 28.05mmol), copper powder (2.67g,42.08mmol), K2CO3A mixture of (11.63g, 84.17mmol), 18-crown-6 (0.59g,2.24mmol) and 1, 2-dichlorobenzene (100mL) was stirred at 190 ℃ under reflux for 20 hours. After cooling to room 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 by column gave compound (B-3) (4g,8.28mmol, 29.60%).
Preparation of Compound (B)
To a reaction vessel containing a solution of NaH (0.49g,12.43mmol, 60% dispersion in mineral oil) in DMF (20mL) was added a solution of compound (B-3) (4g,8.28mmol) in DMF (20 mL). After 1 hour, a solution of 2-chloro-4, 6-diphenyltriazine (2.66g,9.94mmol) in DMF (20mL) was added. After stirring for 12 hours, distilled water was added, and the resulting solid was filtered under reduced pressure. Recrystallization from ethyl acetate and DMF gave compound (B) (3.5g,4.90mmol, 59.21%).
Preparation example 3: preparation of Compound (C)
Preparation of Compound (C-1)
To a solution of 1, 2-cyclohexanedione (42.52g,379.26mmol) in ethanol (1000mL) was slowly added 2-naphthylhydrazine (20g,126.42 mmol). Acetic acid (0.28mL,5.05mmol) was added and the mixture was heated to 40 ℃. After 2 hours, the mixture was cooled, and distilled water was added thereto. The resulting solid was filtered under reduced pressure to give compound (C-1) (17g,67.37mmol, 53.47%).
Preparation of Compound (C-2)
To a solution of compound (C-1) (17g,67.37mmol) in acetic acid (100mL) was added trifluoroacetic acid (10 mL). After stirring at room temperature for 2 hours, 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 by column gave compound (C-2) (11g,46.75mmol, 69.39%).
Preparation of Compound (C-3)
According to the same procedure as that for the synthesis of compound (B-3), compound (C-3) (10g,32.11mmol, 68.69%) was obtained.
Preparation of Compound (C-4)
According to the same procedure as that for the synthesis of compound (C-1), compound (C-4) (12g,29.88mmol, 93.07%) was obtained.
Preparation of Compound (C-5)
According to the same procedure as that for the synthesis of compound (C-2), compound (C-5) (6g,15.68mmol, 52.50%) was obtained.
Preparation of Compound (C)
According to the same procedure as that for the synthesis of compound (B), compound (C) (5g,8.14mmol, 51.95%) was obtained.
Preparation example 4: preparation of Compound (D)
Preparation of Compound (D-2)
Compound (D-2) (11g,38.02mmol, 89.22%) was obtained according to the same procedure as in Synthesis example (A-1) but using compound (D-1).
Preparation of Compound (D-3)
Compound (D-3) (8g,31.09mmol, 81.78%) was obtained according to the same procedure as that for the synthesis of Compound (A-2).
Preparation of Compound (D)
Compound (D) (6g,12.30mmol, 38.70%) was obtained according to the same procedure as that for the synthesis of Compound (B).
Preparation example 5: preparation of Compounds E and F
Preparation of Compound (E-2)
Compound (E-2) (15g,51.85mmol, 86.51%) was obtained according to the same procedure as that for the synthesis of compound (A-1) but using compound (E-1).
Preparation of Compound (E-3)
According to the same procedure as that for the synthesis of compound (A-2), compound (E-3) (6g,23.31mmol, 44.97%) was obtained.
Preparation of Compound (E)
According to the same procedure as that for the synthesis of compound (B), compound (E) (5g,10.25mmol, 43.99%) was obtained.
Preparation of Compound (F-1)
According to the same procedure as that for the synthesis of compound (A-2), compound (F-1) (3g,11.65mmol, 22.48%) was obtained.
Preparation of Compound (F)
According to the same procedure as that for the synthesis of compound (B), compound (F) (3g,6.15mmol, 52.81%) was obtained.
Preparation example 6: preparation of Compounds (G) and (H)
Preparation of Compound (G-1)
Carbazole (20g,119.6mmol), iodobenzene (20mL, 179.41mmol), copper (11.4g,179.41mmol), K2CO3A mixture of (49g, 358.8mmol), 18-crown-6 (2.5g,9.56mmol) and 1, 2-dichlorobenzene (100mL) was stirred at 190 ℃ for 12 hours. After cooling to room 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 by column gave compound (G-1) (22G,90.42mmol, 75.60%).
Preparation of Compound (G-2)
According to the same procedure as that for the synthesis of compound (A-4), compound (G-2) (25G,77.59mmol, 85.81%) was obtained.
Preparation of Compound (G-3)
According to the same procedure as that for the synthesis of compound (A-5), compound (G-3) (11G,38.31mmol, 49.37%) was obtained.
Preparation of Compound (G-4)
According to the same procedure as that for the synthesis of compound (A-1), compound (G-4) (12G,32.84mmol, 85.72%) was obtained.
Preparation of Compound (G-5)
According to the same procedure as that for the synthesis of compound (A-2), the reaction was carried out for 4 hours to give compound (G-5) (6G,17.99mmol, 54.80%).
Preparation of Compound (G)
According to the same procedure as that for the synthesis of compound (B), compound (G) (7G,12.39mmol, 68.91%) was obtained.
Preparation of Compound (H-1)
According to the same procedure as that for the synthesis of compound (A-2), the reaction was carried out for 4 hours to give compound (H-1) (2g,5.99mmol, 18.26%).
Preparation of Compound (H)
According to the same procedure as that for the synthesis of compound (B), compound (H) (1.7g,3.01mmol, 50.26%) was obtained.
Organic electroluminescent compounds (TA, TB and TC) were prepared according to the procedures of preparation examples (1) to (6). Substituent (Ar) of the organic electroluminescent compounds thus obtained1And Ar2) And of these compounds1The H NMR and MS/FAB data are listed in tables 1 and 2 below.
TABLE 1
TABLE 2
EXAMPLES 1-10 fabrication of OLED Using the organic electroluminescent Compounds of the present invention
OLED devices are fabricated using the electroluminescent compounds of the present invention.
First, a transparent electrode ITO film (15 Ω/□) (available from samsung corning) for OLED made of glass was ultrasonically cleaned with trichloroethylene, acetone, ethanol and distilled water in order, and stored in isopropyl alcohol before use.
Then, the ITO substrate was set in a substrate holder (holder) of a vacuum vapor deposition apparatus, 4' -tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA), represented by the following chemical structural formula, was placed in a cell (cell) of the vacuum vapor deposition apparatus, and then evacuated to a degree of vacuum in the cell of up to 10-6And (4) supporting. A current was applied to the cell to evaporate the 2-TNATA, thereby vapor-depositing a hole injection layer having a thickness of 60 nm on the ITO substrate.
Then, N ' -di (. alpha. -naphthyl) -N, N ' -diphenyl-4, 4' -diamine (NPB) was charged into another cell of the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate the NPB, thereby vapor-depositing a hole transport layer having a thickness of 20 nm on the hole injection layer.
A chamber of a vapor deposition apparatus is charged with a compound of the invention (which has been at 10)-6Purified by vacuum sublimation under torr) (e.g., compounds TA8-H4-H2), and an electroluminescent dopant (e.g., compound (piq)2Ir (acac)) was added to the other chamber. The two materials were doped at 4-10 mol% concentration by evaporation at different rates to vapor deposit a 30 nm thick electroluminescent layer on the hole transport layer.
Then, tris (8-hydroxyquinoline) aluminum (III) (Alq) represented by the following structural formula was vapor-deposited as an electron transport layer having a thickness of 20 nm, and 8-hydroxyquinoline lithium (lithium quinolate) (Liq) was vapor-deposited as an electron injection layer having a thickness of 1 to 2 nm. Then, an Al cathode having a thickness of 150 nm was vapor-deposited using another vacuum vapor deposition apparatus to manufacture an OLED.
EXAMPLES 11-20 production of OLED Using the electroluminescent Compounds of the invention
An OLED was fabricated according to the same procedure as the OLEDs of examples 1-10, but using the compound of the present invention (e.g., compound TA4-H4-H4) as a matrix material and an organic iridium complex represented by the following formula (Ir (ppy)3) As an electroluminescent dopant.
Comparative examples 1 and 2 fabrication of OLED Using conventional electroluminescent Material
An OLED was fabricated according to the same procedure as in examples 1 and 11 of the present invention, except that bis (2-methyl 8-quinolate) (p-phenylphenolate) aluminum (III) (BALq) was added to another chamber of the vacuum vapor deposition apparatus instead of the electroluminescent compound of the present invention as a host material.
At 1000cd/cm2The operating voltage and power efficiency of the OLEDs manufactured in examples 1 to 10 and examples 11 to 20, which include the organic electroluminescent compound of the present invention, and comparative examples 1 and 2, which include the conventional electroluminescent compound, were measured, and the results are shown in tables 3 and 4.
As can be seen from tables 3 and 4, the organic electroluminescent compounds developed according to the present invention have superior properties in device performance compared to conventional materials.
TABLE 3
TABLE 4
As can be seen from table 3, the compound developed by the present invention shows superior performance in light emitting properties compared to conventional materials. The device manufactured by the present invention showed excellent current performance, thereby lowering the operating voltage by 1V or more, compared to the device of comparative example 1 manufactured with conventional materials. They also showed a current efficiency performance at least 1.4 times higher than that of the device of comparative example 1 because the luminescence performance was significantly improved.
As can be seen from table 4, when the compounds developed by the present invention were used as a host for green electroluminescence, the devices showed much higher power efficiency than that of comparative example 2 because they had excellent light emitting properties at least 1.6 times higher than the former. Superior light emitting properties were confirmed compared to conventional materials. In particular, the apparatus of example 14 was operated at a reduced voltage of 2.7V as compared with the apparatus of comparative example 1, and the apparatus of example 17 was significantly lowerThe working voltage is 5.5V and is 1000cd/m2The power efficiency of (A) is 15.9 lm/.
Therefore, a device emitting red or green light using the electroluminescent compound of the present invention as a host material exhibits excellent light emitting properties while decreasing the operating voltage, which results in an increase in power efficiency of the device emitting particularly green light by 5.1 to 7.7lm/W, with the result that power consumption is improved.

Claims (7)

1. An organic electroluminescent compound selected from the group consisting of:
wherein:
Ar1selected from (C6-C60) aryl;
Ar2selected from (C6-C60) aryl and (C3-C60) heteroaryl;
Ar2aryl of (A) is further selected fromSubstituted with one or more of the following substituents: (C3-C60) heteroaryl and (C6-C60) aryl-substituted (C3-C60) heteroaryl,
Ar2the heteroaryl group of (a) may be further substituted with one or more substituents selected from: (C6-C60) aryl, (C3-C60) heteroaryl, and (C6-C60) aryl-substituted (C3-C60) heteroaryl.
2. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
3. The organic electroluminescent device of claim 2, wherein the device comprises a first electrode; a second electrode; and one or more organic layers interposed between the first and second electrodes, the organic layers comprising one or more organic electroluminescent compounds according to claim 1 and one or more phosphorescent dopants.
4. The organic electroluminescent device according to claim 3, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds.
5. The organic electroluminescent device according to claim 3, wherein the organic layer further comprises one or more metals selected from the group consisting of group 1, group 2, fourth and fifth periodic transition metals, lanthanide metals and d-transition elements of the periodic table of elements or complexes formed therefrom.
6. The organic electroluminescent device according to claim 3, wherein the organic layer comprises an electroluminescent layer and a charge generation layer.
7. The organic electroluminescent device of claim 3, wherein the device is a white light-emitting organic electroluminescent device, and the organic layer simultaneously comprises one or more organic electroluminescent layers emitting blue, red, or green light.
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