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KR-102962231-B1 - ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

KR102962231B1KR 102962231 B1KR102962231 B1KR 102962231B1KR-102962231-B1

Abstract

The present invention relates to a compound having the chemical formula M( LA ) x ( LB ) y ( LC ) z , wherein, in the said chemical formula, the ligand LA is and the ligand L B is and the ligand L C is Initiates a phosphorus compound. In the chemical formula M(L A ) x (L B ) y (L C ) z , M is a metal having an atomic number greater than 40, x is 1 or 2, y is 0, 1 or 2, z is 0, 1 or 2, x + y + z is the oxidation state of metal M, A1 to A8 are carbon or nitrogen, ring B is bonded to ring A via CC bonds, M is bonded to ring A via MC bonds, X is selected from the group consisting of O, S, Se, CRR' and NR1 , rings C and D are each independently pentagonal or hexagonal carbon-cyclic or heterocyclic rings, R3 represents single substitution, double substitution, or non-substitution, R2 , RC , and RD each independently represent single substitution, double substitution, triple substitution, quadruple substitution, or non-substitution, and R4 represents single substitution, double It represents a permutation, triple permutation, or quadruple permutation, and 1 or more R 4 are quinary or hexacyclic rings that can be further substituted with R E , where R E represents a single permutation, double permutation, triple permutation, or quadruple permutation, or no permutation, and each R substituent is independently selected from various moiety, and any adjacent R substituents are arbitrarily combined to form a ring.

Inventors

  • 부드롤트 피에르 루크 티
  • 웬트 하베이
  • 시아 추안준

Assignees

  • 유니버셜 디스플레이 코포레이션

Dates

Publication Date
20260507
Application Date
20230920
Priority Date
20141112

Claims (20)

  1. A material for use in an organic light-emitting diode (OLED), comprising a compound having the chemical formula M(L A ) x (L B ) y (L C ) z : In the above chemical formula, The ligand L A is And, Ligand L B is is, The ligand L C is And, M is Ir, and x is 1 or 2, and y is 0, 1, or 2, and z is 0, 1, or 2, and At least one of y and z is 1 or greater, and x + y + z is the oxidation state of metal M, and A1 , A2 , A3 , and A4 are carbon, and A5 , A6 , A7 , and A8 are carbon, or exactly one of A5 , A6 , A7 , and A8 is nitrogen and the rest are carbon, Ring B is bonded to Ring A through CC bonds, and M is bonded to ring A through MC bonding, and X is selected from the group consisting of O, S, and NR 1 , and Ring C is benzene, ring D is pyridine, and R3 represents a single substitution, a double substitution, or a non-substitution, and R2 , RC , and RD each independently represent a single, double, triple, or quadruple substitution, or a non-substitution, and R 4 represents a single, double, triple, or quadruple substitution, and One or more R₄s are a six-membered aromatic heterocyclic ring having one or more nitrogen atoms where the only heteroatom is nitrogen, and can be further substituted with RE , wherein the six-membered aromatic heterocyclic ring is bonded to (i) a carbon atom at the para position relative to the nitrogen atom of ring B or (ii) a carbon atom at the para position relative to the carbon atom of ring B bonded to ring A, provided that if one or more R₄s are a six-membered aromatic heterocyclic ring having only one nitrogen atom, X is NR₁ , and R E represents a single substitution, double substitution, triple substitution, or quadruple substitution, or a non-substitution, and R, R', R1 , R2 , R3 , R4 , RC , RD, RX , RY , RZ , and RE are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof, and Any adjacent substituents of R, R', R1 , R2 , R3 , R4 , RC , RD , RX , RY , RZ , and RE are arbitrarily combined to form a ring.
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  3. In claim 1, the compound is a material for use in an OLED having the chemical formula M( LA ) 2 ( LC ) or the chemical formula M( LA )( LB ) 2 .
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  5. In claim 1, X is a material for use in an OLED that is O or NR 1 .
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  8. In claim 1, L A is a material for use in an OLED selected from the group consisting of the following chemical formulas: Here, It is bonded to (i) a carbon atom at the para position relative to the nitrogen atom of the pyridine ring or (ii) a carbon atom at the para position relative to the carbon atom of the pyridine ring that is bonded to the benzene ring.
  9. In claim 1, L A is a material for use in an OLED selected from the group consisting of the following chemical formulas: (In the above L A1 ~ L A96 , R A1 ~ R A4 have the following structures: having, RB1 and RB2 have the following structure: has), (In the above L A183 ~ L A342 , L A375 ~ L A486 , L A503 ~ L A614 , R A5 ~ R A8 have the following structure: Having, R B1 and R B2 have the following structure: It has, and R C1 ~ R C2 have the following structure: has
  10. In claim 1, L B is a material for use in an OLED selected from the group consisting of the following chemical formulas:
  11. In claim 1, a material for use in an OLED, wherein L C is selected from the group consisting of the following chemical formulas:
  12. In paragraph 9, the compound is selected from the group consisting of compounds 1 to 25,830 (provided that compounds in which k is 97 to 182, 343 to 374, 487 to 502 and 615 to 630 are excluded), Here, each compound x has the chemical formula Ir(L A k )(L B j ) 2 , and A material for use in an OLED where x = 630 j + k - 630, k is an integer from 1 to 96, 183 to 342, 375 to 486, and 503 to 614, j is an integer from 1 to 41, and L B1 to L B41 are defined as follows:
  13. In paragraph 9, the compound is selected from the group consisting of compounds 25,831 to 34,020 (provided that compounds in which k is 97 to 182, 343 to 374, 487 to 502 and 615 to 630 are excluded), Here, each compound x has the chemical formula Ir(L A k ) 2 (L C i ) and x = (630 i + k - 630) + 25,830, where k is an integer from 1 to 96, 183 to 342, 375 to 486, and 503 to 614, and i is an integer from 1 to 13; and L C1 to L C13 are materials for use in an OLED defined as follows:
  14. Organic layer containing a compound having the chemical formula M(L A ) x (L B ) y (L C ) z : In the above chemical formula, The ligand L A is And, Ligand L B is is, The ligand L C is And, M is Ir, and x is 1 or 2, and y is 0, 1, or 2, and z is 0, 1, or 2, and At least one of y and z is 1 or greater, and x + y + z is the oxidation number of metal M, and A1 , A2 , A3 , and A4 are carbon, and A5 , A6 , A7 , and A8 are carbon, or exactly one of A5 , A6 , A7 , and A8 is nitrogen and the rest are carbon, Ring B is bonded to Ring A through CC bonds, and M is bonded to ring A through MC bonding, and X is selected from the group consisting of O, S, and NR 1 , and Ring C is benzene, ring D is pyridine, and R3 represents a single substitution, a double substitution, or a non-substitution, and R2 , RC , and RD each independently represent a single, double, triple, or quadruple substitution, or a non-substitution, and R 4 represents a single, double, triple, or quadruple substitution, and One or more R₄s are a six-membered aromatic heterocyclic ring having one or more nitrogen atoms where the only heteroatom is nitrogen, and can be further substituted with RE , wherein the six-membered aromatic heterocyclic ring is bonded to (i) a carbon atom at the para position relative to the nitrogen atom of ring B or (ii) a carbon atom at the para position relative to the carbon atom of ring B bonded to ring A, provided that if one or more R₄s are a six-membered aromatic heterocyclic ring having only one nitrogen atom, X is NR₁ , and R E represents a single substitution, double substitution, triple substitution, or quadruple substitution, or a non-substitution, and R, R', R1 , R2 , R3 , R4 , RC , RD, RX , RY , RZ , and RE are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, nitrile, isonitrile, sulfanyl, phosphino, and combinations thereof, and Any adjacent substituents of R, R', R1 , R2 , R3 , R4 , RC , RD , RX , RY , RZ , and RE are arbitrarily combined to form a ring.
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Description

Organic Electroluminescent Materials and Devices Cross-reference regarding related applications This application is a partial continuation of U.S. Patent Application No. 14/539,412 filed on November 12, 2014, the entire contents of which are incorporated herein by reference. This application also claims priority to U.S. Provisional Patent Application No. 62/089,397 filed on December 9, 2014, under 35 U.S.C. §119(e), the entire contents of which are incorporated herein by reference. Parties to the joint research agreement The invention was completed by one or more of the parties Regents of the University of Michigan, Princeton University, The University of Southern California, and The Universal Display Corporation pursuant to a joint industry-academia research agreement, on their behalf and/or in connection therewith. The agreement entered into force on and prior to the date the invention was completed, and the invention was completed as a result of activities performed within the scope of the agreement. Field of invention The present invention relates to a compound for use as an emitter, and a device comprising the same, such as an organic light-emitting diode. Optoelectronic devices using organic materials are becoming increasingly important for various reasons. Since many of the materials used to manufacture such devices are relatively inexpensive, organic optoelectronic devices have potential in terms of economic advantages over inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, can make them highly suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light-emitting devices (OLEDs), organic phototransistors, organic photovoltaics, and organic photodetectors. In the case of OLEDs, organic materials can have performance advantages over conventional materials. For example, the wavelength at which the organic light-emitting layer emits light can generally be easily controlled with a suitable dopant. OLEDs utilize organic thin films that emit light when voltage is applied across the device. OLEDs are an increasingly important technology for use in applications such as flat panel displays, lighting, and backlighting. Various OLED materials and shapes are described in U.S. Patents No. 5,844,363, 6,303,238, and 5,707,745, the full text of which is incorporated herein by reference. One application of phosphorescent emitting molecules is a full-color display. Industrial standards for such displays require pixels tuned to emit specific colors referred to as "saturated" colors. In particular, these standards require saturated red, green, and blue pixels. Color can be measured using CIE coordinates known in the art. An example of a green luminescent molecule is tris(2-phenylpyridine) iridium, represented as Ir(ppy) ₃ having the following chemical formula: In the chemical formulas herein and below, the applicant illustrates the coordination bond from nitrogen to a metal (hereafter Ir) as a straight line. In this document, the term "organic" includes not only polymeric materials that can be used to manufacture organic optoelectronic devices, but also small molecule organic materials. "Small molecule" refers to any organic material that is not a polymer, and "small molecules" may actually be quite large. Small molecules may contain repeating units in some situations. For example, using a long-chain alkyl group as a substituent does not remove the molecule from the "small molecule" type. Small molecules may also be incorporated into the polymer, for example, as side chains on the polymer main chain or as part of the main chain. Small molecules may also serve as the core part of a dendrimer, which consists of a series of chemical shells formed on the core part. The core part of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a "small molecule," and it has been found that all dendrimers commonly used in the OLED field are small molecules. As used herein, "top part" means the part furthest from the substrate, and "bottom part" means the part closest to the substrate. If the first layer is described as being "located at the top part of the second layer," the first layer is positioned far from the substrate. If the first layer is not specified as being "in contact" with the second layer, other layers may exist between the first layer and the second layer. For example, even though various organic layers may exist between the cathode and the anode, the cathode may be described as being "located on the top of the anode." As used herein, "solution processability" means that it can be dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension, and/or deposited from a liquid medium. If a ligand is found to directly contribute to the photoactive properties of a luminescent material, the ligand may be referred to