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  • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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  • C09K2211/1025—Heterocyclic compounds characterised by ligands
  • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
  • C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur

Definitions

• the present invention relates to a novel compound and an organic electroluminescent device comprising the same.
• the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
• the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
• a host / dopant system may be used as the light emitting material.
• the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
• a metal complex compound containing heavy atoms such as Ir and Pt.
• NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injection layer and the electron transport layer, and anthracene derivatives are used as the light emitting material.
• a metal complex compound including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 is used as a blue, green, or red phosphorescent dopant material, and CBP is used as a phosphorescent host material.
• the conventional light emitting materials have good light emission characteristics, they are not satisfactory in terms of lifespan of the organic EL device, and thus, development of a light emitting material having excellent performance is required.
• an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
• the present invention provides a compound represented by the following formula (1).
• A is O (oxygen) or S (sulfur)
• X 1 to X 4 are each independently CR 1 or N (nitrogen)
• Y 1 and Y 2 , Y 2 and Y 3 are independently CR 1 or N (nitrogen)
• Y 1 and Y 2 , Y 2 and Y 3 are independently CR 1 or N (nitrogen)
• Y 1 and Y 2 , Y 2 and Y 3 are each independently CR 1 or N (nitrogen)
• One of Y 3 and Y 4 forms a condensed ring with the compound represented by Formula 2
• one of Y 1 to Y 4 that does not form a condensed ring is CR 2 or N (nitrogen), wherein N (nitrogen) Must contain at least one
• Z 1 to Z 4 are each independently CR 3 or N (nitrogen),
• R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6- C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, (C 6 - of C 40 aryl) C of 1 - C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, and a C 6 ⁇ C 40 of Selected from the group consisting of arylsilyl groups, may be bonded to adjacent groups to form a condensed ring,
• Ar 1 is hydrogen, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 Aryl group, nuclear atoms 5 to 40 heteroaryl C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, (C 6 -C 40 aryl) C 1 -C 40 alkyl group, C 3 ⁇ C 40 of is selected from cycloalkyl groups, 3 to 40 nuclear atoms heterocycloalkyl group, the group consisting of C 1 ⁇ C 40 alkyl silyl group, and a C 6 ⁇ C 40 aryl group in the silyl.
• R 1 to R 3 may combine with an adjacent group to form a condensed ring (condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, condensed heteroaromatic ring, or a combination thereof).
• the silyl group and the arylsilyl group are deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 40 aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, (C 6 to C 40 aryl) C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 hetero
• Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
• alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
• Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
• alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
• Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
• alkynyl include, but are not limited to, ethynyl, 2-propynyl, and the like.
• Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, a single ring or a combination of two or more rings, and may also include a form in which two or more rings are simply attached or condensed with each other.
• Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
• Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon of 5 to 40 nuclear atoms (number of atoms including carbon), at least one carbon in the ring, Preferably one to three carbons are substituted with heteroatoms such as N, O, S or Se.
• Heteroaryl can be interpreted that two or more rings may be attached in a simple or fused form with each other, and also include a condensed form with an aryl group.
• heteroaryl examples include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
• Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R is aryl having 6 to 60 carbon atoms.
• R is aryl having 6 to 60 carbon atoms.
• Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy and the like.
• Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It can be interpreted as being included.
• alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
• Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
• Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
• Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
• Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O or S and Are substituted with the same hetero atom.
• heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
• Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms
• arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.
• the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises a.
• the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer.
• the compound represented by Formula 1 when the compound represented by Formula 1 is a light emitting layer, the compound represented by Formula 1 may be a blue, green or red phosphorescent host material.
• the present invention not only has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), but also has a wide energy band gap, It is a feature to provide a compound represented by the formula (1) that can increase the binding force.
• 'CBP' 4,4-dicarbazolybiphenyl
• a heterocyclic moiety preferably an indole derivative moiety (moiety) is bonded to the end of benzothienopyridine or benzofuropyridine Fused). Since the benzothienopyridine or benzofuropyridine skeleton has a high triplet energy level, when the compound represented by Formula 1 of the present invention is used in an organic electroluminescent device, the phosphorescence characteristics of the device are improved. At the same time, the hole injection ability, hole transport ability, luminous efficiency, driving voltage, and lifetime characteristics can be improved.
• the compound represented by Formula 1 of the present invention has a wide bandgap (sky blue to red) due to the indole derivative moiety bound to the terminal of the benzocyanopyridine or benzofuropyridine skeleton, Since the bonding force can be increased, it can exhibit excellent properties as a host material of the light emitting layer, specifically, a blue, green and / or red phosphorescent host material, compared to the conventional CBP.
• the compound represented by the formula (1) of the present invention exhibits a high glass transition temperature because a variety of substituents (R 1 to R 3 and Ar 1 ) is bonded to significantly increase the molecular weight of the compound, which is higher than the conventional CBP May have thermal stability.
• the portion of the Y 1 to Y 4 that does not form a condensed ring preferably contains one or more N.
• all of X 1 to X 4 are CR 1 or include one or more N, and all of Z 1 to Z 4 are preferably CR 3 or one or more N.
• Ar 1 substituted in the indole derivative moiety is preferably a C 6 ⁇ C 40 aryl group or a heteroaryl group of 5 to 40 nuclear atoms.
• the aryl group or heteroaryl group of Ar 1 Deuterium, halogen, cyano group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 aryl amine group, a (C 6 ⁇ C 40 aryl) C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group and C 6 to C 40 arylsilyl It may be substituted with one or more substituents selected from the group consisting of groups, and when having a plurality of substituents, each substituent may be the same or different.
• R 1 to R 3 and Ar 1 which are substituents (functional groups) of the compound represented by Formula 1 of the present invention include the following examples (S1 to S138), but are not limited thereto.
• Ar 1 in the substituent (functional group) of the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of structures represented by S-1 to S-39.
• the compound represented by Chemical Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Chemical Formulas 3 to 8, but is not limited thereto.
• the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Formulas C1 to C18, but is not limited thereto.
• A is more preferably S.
• Specific examples of the compound represented by Formula 1 of the present invention include the following compounds (C-1 to C-578), but is not limited thereto.
• Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.
• the present invention provides an organic electroluminescent device comprising a compound represented by Chemical Formula 1, preferably a compound represented by Chemical Formulas 3 to 8.
• the present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above.
• the compound represented Preferably the compound represented by Formula 3-8 is included. In this case, the compounds represented by Formulas 3 to 8 may be used alone or in combination of two or more.
• the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, preferably a hole injection layer, a hole transport layer, a light emitting layer or an electron transport layer, more preferably It may be a light emitting layer.
• the organic electroluminescent device may include a host material in the light emitting layer.
• the compound represented by Formula 1 may be used as the host material.
• the compound represented by Chemical Formula 1 is used as a light emitting layer of the organic EL device, preferably a blue, green or red phosphorescent host material of the light emitting layer, the binding force between the holes and the electrons in the light emitting layer is increased, so that the efficiency of the organic EL device is increased. (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
• the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be formed of a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
• the electron injection layer may be further stacked on the electron transport layer.
• the organic electroluminescent 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 also a structure in which an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
• the material that can be used as the anode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, gold or alloys 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 or polyaniline; And carbon black and the like can be used.
• metals such as vanadium, chromium, copper, zinc, gold or alloys 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
• the material usable as the negative electrode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, Or metals such as lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
• the organic material layer included in the organic electroluminescent device according to the present invention is known in the art except for using the compound represented by Formula 1 in any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer It can be made of a material.
• the material usable as the substrate included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples may include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
• Such an organic electroluminescent device of the present invention may be manufactured by a method known in the art, the light emitting layer included in the organic material layer may be manufactured 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.
• a CORE2-B 6g (yield: 67%) was obtained in the same manner as in ⁇ Step 1> of Preparation Example 1, except that CORE2-A was used instead of CORE1-A-1.
• the compound Mat-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.
• a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
• ITO Indium tin oxide
• Example 2 The same procedure as in Example 1 was repeated except that the compounds Mat-2 to Mat-34 synthesized in Synthesis Examples 2 to 34 were used instead of the compound Mat-1 to be used as the light emitting host material in Example 1 To produce a green organic electroluminescent device.
• a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 used as the light emitting host material in forming the light emitting layer in Example 1.
• the structure of CBP used is as follows.
• Example 1 Sample Host Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 1 Mat-1 6.50 520 41.0 Example 2 Mat-2 6.61 523 41.2 Example 3 Mat-3 6.60 523 40.8 Example 4 Mat-4 6.58 523 41.1 Example 5 Mat-5 6.70 522 41.8 Example 6 Mat-6 6.70 520 41.3 Example 7 Mat-7 6.51 521 41.4 Example 8 Mat-8 6.66 520 40.9 Example 9 Mat-9 6.50 520 41.0 Example 10 Mat-10 6.45 519 41.5 Example 11 Mat-11 6.60 521 41.3 Example 12 Mat-12 6.55 518 41.1 Example 13 Mat-13 6.70 520 41.2 Example 14 Mat-14 6.50 523 41.3 Example 15 Mat-15 6.64 520 41.1 Example 16 Mat-16 6.60 522 41.5 Example 17 Mat-17 6.62 522 40.9 Example 18 Mat-18 6.70 520 41.4 Example 19 Mat-19 6.64 520 41.0 Example 20 Mat-20 6.50 521 41.6 Example 21 Mat-21 6.70 520 41.5 Example 22 Mat-22 6.63 521 41.0 Example 23 Mat-23 6.70
• the green organic electroluminescent devices manufactured in Examples 1 to 34 which use the compounds represented by Chemical Formula 1 of the present invention (Compounds Mat-1 to Mat-34) as the host material of the emission layer, respectively, have conventional CBP. It was confirmed that the green organic electroluminescent device of Comparative Example 1 used exhibited superior performance in terms of current efficiency and driving voltage.
• the efficiency (luminescence efficiency and messenger efficiency), lifetime, brightness and driving of the organic electroluminescent device Voltage and the like can be improved. Accordingly, the present invention can provide a full color organic electroluminescent panel with improved performance and lifespan.

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