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Definitions

• the present invention relates to a novel organic light emitting compound and an organic electroluminescent device having improved characteristics such as luminous efficiency, brightness, thermal stability, driving voltage, lifetime by including the same in one or more organic material layers, in particular in the light emitting layer.
• An organic electroluminescent device (hereinafter referred to as an organic EL device) generally has a structure including an anode, a cathode, and an organic material layer therebetween.
• the organic material layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic EL device, for example, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) ), An electron injection layer (EIL), and the like.
• HIL hole injection layer
• HTL hole transport layer
• EML light emitting layer
• ETL electron transport layer
• EIL electron injection layer
• the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors.
• yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
• a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
• a carbazole compound such as CBP (4,4-dicarbazolybiphenyl) is used as the phosphorescent host material, and a metal complex compound containing heavy atoms such as Ir and Pt is widely used as the phosphorescent dopant material.
• CBP 4,4-dicarbazolybiphenyl
• a metal complex compound containing heavy atoms such as Ir and Pt is widely used as the phosphorescent dopant material.
• CBP which is currently used phosphorescent host material
• Tg glass transition temperature
• An object of the present invention is to provide an organic light emitting compound having better thermal stability and an organic EL device having improved characteristics such as luminous efficiency, brightness, power efficiency, driving voltage, and lifespan.
• the present invention to achieve the above object provides a compound represented by the following formula (1).
• X 1 and X 2 are each independently selected from the group consisting of CR 1 R 2 , O, S, NR 3 and SiR 4 R 5 ;
• Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ⁇ C 60 alkyl group, substituted or unsubstituted C 2 ⁇ C 60 alkenyl group, substituted or unsubstituted C 2 ⁇ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 60 arylamine group, and a substituted or unsubstituted silyl group;
• R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ⁇ C 60 alkyl group, substituted or unsubstituted C 2 ⁇ C 60 alkenyl group, substituted or unsubstituted C 2 ⁇ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 60 aryl group and a substituted or unsubstituted amine selected from the group consisting of unsubsti
• n and m are each independently an integer from 1 to 4;
• At least one Ar 3 is the same or different from each other, at least one Ar 4 is the same or different from each other, and each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 ⁇ C 60 alkenyl group, substituted or unsubstituted C 2 ⁇ C 60 Alkynyl group, substituted or unsubstituted C 6 ⁇ C 60 Aryl group, substituted or unsubstituted nuclear atoms of 5 to 60 Heteroaryl group, substituted or unsubstituted C 1 to C 60 alkoxy group, substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted It is selected from the group consisting of a ring heteronuclear alkyl group having 3 to
• the present invention also provides an organic EL device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers is It provides an organic EL device comprising a compound represented by the formula (1).
• the compound of the present invention can be used as a phosphorescent host material of the light emitting layer.
• the compound represented by Chemical Formula 1 of the present invention has excellent thermal stability, light emitting performance, and the like, and the organic EL device including the same may significantly improve characteristics such as light emission performance, driving voltage, and lifetime, so that a full color display panel may be effectively used. Can be applied.
• the compound of the present invention is a phenothiazine (phenoazine) (Formula 1 is one of X 1 and X 2 is NH and the other S is), phenoxazine (phenoxazine) (Formula 1 of X 1 and X 2 Is NH and the other is O), acridine (compound 1 in which X 1 and X 2 are NH and the other is CH 2 ), phenazasiline (in Formula 1) A compound having one of X 1 and X 2 as NH and the other as SiH 2 ), etc., as a central moiety, which facilitates the introduction of various substituents and stabilizes triplet energy levels by the substituents.
• the energy level is controlled to improve the characteristics of the device as a host of blue to red light emitting materials and at the same time improve the electron and / or hole transport capacity, luminous efficiency, driving voltage and lifetime characteristics. Can be. Therefore, it can be applied to not only the light emitting layer but also a hole transport layer, an electron transport layer, and the like.
• the compound of the present invention has a structure represented by the following formula (1).
• X 1 and X 2 are each independently selected from the group consisting of CR 1 R 2 , O, S, NR 3 and SiR 4 R 5 .
• X 1 and X 2 are each independently CR 1 R 2 or SiR 4 R 5 .
• R 1 to R 5 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ⁇ C 60 alkyl group, substituted or unsubstituted C 2 ⁇ C 60 alkenyl group, substituted or unsubstituted C 2 ⁇ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 3 -C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted It is selected from the group consisting of a C 6 ⁇ C 60 arylamine group, and a substituted or unsubsti
• R 1 to R 5 are each independently halogen, cyano, C 1 to C 60 alkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 60 alkoxy group , C aryloxy of 6 ⁇ C 60, C 3 ⁇ C 60 cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C 6 ⁇ C 60 aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.
• Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 ⁇ C 60 alkyl group, substituted or unsubstituted C 2 ⁇ C 60 alkenyl group, substituted or unsubstituted C 2 ⁇ C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted or unsubstituted C 1 to C 60 alkoxy group, Substituted or unsubstituted C 6 to C 60 aryloxy group, substituted or unsubstituted C 3 to C 60 cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 60 nuclear atoms, substituted or unsubstituted C 6 ⁇ C 60 arylamine group, and a substituted or unsubstituted silyl group.
• Ar 1 and Ar 2 are each independently halogen, cyano, C 1 to C 60 alkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 60 alkoxy group , C aryloxy of 6 ⁇ C 60, C 3 ⁇ C 60 cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C 6 ⁇ C 60 aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.
• the aryl groups of Ar 1 and Ar 2 are each independently an unsubstituted C 6 ⁇ C 60 aryl group or C 6 ⁇ C 60 aryl group, a nuclear atom of 5 to 60 hetero A C 6 to C 60 aryl group substituted with an aryl group or an amino group, and the heteroaryl groups of Ar 1 and Ar 2 are each independently an unsubstituted heteroaryl group having 5 to 60 nuclear atoms or a C 6 to C 60 group ; It may be an aryl group, a heteroaryl group having 5 to 60 nuclear atoms or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group.
• the unsubstituted aryl groups of Ar 1 and Ar 2 are each independently phenyl, biphenyl, naphthalene, phenanthrene, anthracene, pyrene ), Fluorine (fluorine) and the like
• the unsubstituted heteroaryl groups of Ar 1 and Ar 2 are each independently pyridine, pyrimidine, pyridazine, pyrazine, Triazine, benzimidazole, quinoline, isoquinoline, isoquinoline, quinoxaline, carbazole, dibenzofuran, dibenzothiophene , Phenanthroline, acridine, phenothiazine, and the like.
• the molecular weight is significantly increased compared to conventional organic light emitting materials (eg, 4,4-dicarbazolybiphenyl (hereinafter referred to as CBP)), thereby improving glass transition temperature and thereby high thermal stability.
• CBP 4,4-dicarbazolybiphenyl
• the device including the compound of the present invention can be improved in characteristics such as durability and lifespan.
• the improvement of device life has a great effect on maximizing performance in full color organic light emitting panel.
• Ar 1 and Ar 2 are each independently an unsubstituted C 6 ⁇ C 60 aryl group; C 6 -C 60 aryl group substituted with a C 6 ⁇ C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms or an amino group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C 6 -C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, or a heteroaryl group having 5 to 60 nuclear atoms substituted with an amino group.
• Ar 1 is an unsubstituted C 6 ⁇ C 60 aryl group; Or a heteroaryl group of 5 to 60 nuclear atoms substituted with an aryl group of C 6 to C 60 , and Ar 2 is substituted with an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms or an amino group C 6 ⁇ C 60 Aryl group; Unsubstituted heteroaryl group having 5 to 60 nuclear atoms; Or a C 6 to C 60 aryl group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a heteroaryl group having 5 to 60 nuclear atoms.
• n and m are each independently an integer of 1-4. Preferably, n and m are each one.
• At least one Ar 3 is the same or different from each other, and at least one Ar 4 is the same or different from each other.
• Ar 3 and Ar 4 may each independently be hydrogen or any substituent, which may include deuterium, halogen, cyano, substituted or unsubstituted C 1 to C 60 alkyl group, substituted or unsubstituted C 2 to C 60 alkenyl group, substituted or unsubstituted C 2 to C 60 alkynyl group, substituted or unsubstituted C 6 to C 60 aryl group, substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms, substituted Or an unsubstituted C 1 to C 60 alkoxy group, a substituted or unsubstituted C 6 to C 60 aryloxy group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted nuclear atom 3 to 60 heterocycloalkyl groups, substitute
• Ar 3 and Ar 4 are each independently halogen, cyano, C 1 ⁇ C 60 alkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group, C 1 ⁇ C 60 alkoxy group , C aryloxy of 6 ⁇ C 60, C 3 ⁇ C 60 cycloalkyl group, the number of nuclear atoms of 3 to 60 heterocycloalkyl group, C 6 ⁇ C 60 aryl amine group and a silyl group one or more substituents selected from the group consisting of It may be substituted by.
• the aryl groups, heteroaryl groups and arylamine groups of Ar 1 to Ar 4 , R 1 to R 5 may each independently have a structure described below, but are not limited thereto.
• Ar 1 to Ar 4 , R 3 to R 5 are as described above.
• the present invention also provides for (i) an anode; (ii) a cathode; And (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by the formula (1).
• the compound represented by Formula 1 may include one kind or two or more kinds.
• the organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer, preferably a light emitting layer.
• the compounds of the present invention may be included in the light emitting layer as blue, green and / or red phosphorescent host and / or fluorescent host materials, particularly preferably phosphorescent host materials.
• the light emitting layer may include a phosphorescent guest material or a fluorescent guest material.
• the organic EL device structure of the present invention is a structure in which one or two or more organic material layers are laminated between electrodes, and for example, (i) an anode, a light emitting layer, a cathode, (ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron
• a transport layer, an electron injection layer, a cathode, (iii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode is mentioned.
• the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between an electrode and an organic material layer.
• the organic material layer including the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method.
• the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
• the organic EL device according to the present invention forms an organic material layer and an electrode by using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. Can be prepared.
• a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet may be used as the substrate.
• the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
• Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
• Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
• the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
• the hole injection layer, the hole transport layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
• reaction solution was filtered through celite and purified by column chromatography to obtain 9,9-dimethyl-10-phenyl-9,10-dihydroacridine (3.4g, yield 80%).
• reaction solution was filtered through celite and purified by column chromatography to give 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine (2.3g, yield 60%).
• reaction solution was filtered through celite and purified by column chromatography to obtain 10- (4,6-diphenylpyridin-2-yl) -9,9-dimethyl-9,10-dihydroacridine (6.2g, yield 80% )
• Mat 1-A (5 g, 12.2 mmol) synthesized in Preparation Example 1
• Mat 1-B (6.3 g, 1 equivalent) synthesized in Preparation Example 2
• tetrakis (triphenylphosphine) palladium (0) (0.7 g, 5 mol%)
• potassium carbonate (5 g, 3 equiv) were added to a 250 mL round flask with 1,4-dioxane (61 mL) and H 2 O (18 mL) and stirred under reflux for 3 hours under a nitrogen atmosphere.
• Mat 2-B (3.3 g, yield 60%) was synthesized in the same manner as in Preparation Example 2, using 2-bromo-4,6-diphenylpyrimidine instead of 2-Bromo-4,6-diphenylpyridine.
• Mat 2-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 2 (6g, yield 68%).
• Mat 3-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 3 (5.8g, 66% yield).
• Mat 4-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 4 (5.2g, yield 67%).
• Mat 5-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 5 (4.8g, 62% yield).
• Mat 6-B (4g, 73% yield) was obtained by the same procedure as Preparation Example 2, using 2- (4-bromophenyl) naphthalene instead of 2-Bromo-4,6-diphenylpyridine.
• Mat 6-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 6 (5.1g, 61% yield).
• Mat 7-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 7 (3.2g, yield 37%).
• Mat 8-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 8 (3.6g, yield 41%).
• Mat 9-B was used in place of Mat 1-B to obtain Mat 9 (5.5 g, yield 62%).
• Mat 10-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 10 (4.9g, yield 60%).
• Mat 11-A (1.6g, 73% yield) was obtained by performing the same procedure as Preparation Example 1 using 2-bromo-4,6-diphenylpyridine instead of bromobenzene.
• Mat 11-A instead of Mat 1-A was carried out in the same manner as in Synthesis Example 1 to obtain Mat 11 (5g, yield 57%).
• Mat 12-A (1.8 g, yield 80%) was obtained by performing the same procedure as Preparation Example 1 using 2 2-bromonaphthalene instead of bromobenzene.
• Mat 12-A instead of Mat 1-A was carried out in the same manner as in Synthesis Example 1 to obtain Mat 12 (5.6g yield 72%).
• Mat 12-A was used instead of Mat 1-A and Mat 2-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis example 1 to obtain Mat 13 (4.2 g, yield 60%).
• Mat 14-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 14 (3.9g, yield 36%).
• Mat 15-B (3.5 g, yield 65%) was obtained by the same procedure as Preparation Example 2 using 2- (4-bromophenyl) -4,6-diphenylpyridine instead of 2-Bromo-4,6-diphenylpyridine. .
• Mat 15-B instead of Mat 1-B was carried out the same procedure as in Synthesis Example 1 to obtain Mat 15 (4.8g, yield 50%).
• Mat 16-A was used instead of Mat 1-A and Mat 16-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1, thereby obtaining Mat 16 (3.4 g, yield 63%).
• Mat 17-B (4.2 g, yield 73%) was obtained by the same procedure as Preparation Example 2 using 2-methylquinoline instead of 2-Bromo-4,6-diphenylpyridine.
• Mat 16-A was used instead of Mat 1-A
• Mat 17-B was used instead of Mat 1-B to carry out the same procedure as Synthesis Example 1, thereby obtaining Mat 17 (3.2 g, yield 63%).
• Mat 16-A was used instead of Mat 1-A
• Mat 18-B was used instead of Mat 1-B
• Mat 18 (3.6 g, yield 58%) was obtained in the same manner as in Synthesis example 1.
• Mat 19-A (1.1 g, yield 50%) was obtained in the same manner as in Preparation Example 1, using 9,9-diphenyl-9,10-dihydroacridine instead of 9,9-Dimethyl-9,10-dihydroacridine. .
• Mat 19-A instead of Mat 1-A was carried out the same procedure as in Synthesis Example 1 to obtain Mat 19 (2.3g, 41% yield).
• Mat 20-A instead of Mat 1-A
• Mat 20-B instead of Mat 1-B was carried out in the same manner as in Synthesis Example 1 to obtain Mat 20 (2.1 g, yield 32%).
• Mat 21-B (4.2 g, yield 76%) was obtained in the same manner as in Preparation Example 2, using 10H-phenoxazine instead of 9,9-Dimethyl-9,10-dihydroacridine.
• Mat 21-B was used in place of Mat 1-B to obtain Mat 21 (4.6 g, 55% yield).
• Mat 22-A (1.3 g, yield 45%) was obtained by the same procedure as in Preparation Example 1, using 5,10-dihydrophenazine instead of 9,9-dimethyl-9,10-dihydroacridine and using 2 equivalents of bromobenzene. .
• Mat 22-A was used instead of Mat 1-A and Mat 2-B was used instead of Mat 1-B to carry out the same procedure as in Synthesis Example 1 to obtain Mat 22 (4.6 g, yield 55%).
• a glass substrate coated with ITO Indium tin oxide
• ITO Indium tin oxide
• a solvent such as isopropyl alcohol, acetone, methanol, etc.
• UV OZONE cleaner Power sonic 405, Hwasin Tech
• An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound of the present invention as a light emitting host material in forming the emission layer.
• CBP CBP
• Example 1-22 For each organic EL device produced in Example 1-22 and Comparative Example 1, the driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

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