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DE-102021126540-B4 - Organic metal compound, organic light-emitting diode and organic light emission device with the compound

DE102021126540B4DE 102021126540 B4DE102021126540 B4DE 102021126540B4DE-102021126540-B4

Abstract

Organic metal compound with the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L A has the following structure of formula 2; L B is an auxiliary ligand with the following structure of formula 4; where m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n equals 3; where R1 is an unsubstituted or substituted C1 - C20 alkyl, an unsubstituted alicyclic C4 - C30 group, or an unsubstituted or substituted aromatic C6 - C30 group, and R2 and R3 are independently hydrogen or deuterium, or R1 as defined above, and R2 and R3 form an unsubstituted aromatic C6 - C20 ring; and A has the following structure of formula 3: where each of X 1 to X 4 is independent CR 4 ; X 5 to X 7 are independent of CR 5 ; X 8 to X 11 independent CR 6 is; Each R 4 to R 6 is independently hydrogen, deuterium, or unsubstituted C 1 -C 20 -alkyl; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR 4 from X 1 to X 4 , and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X 1 to X 4 , or an imidazole ligand in formula 2 is bonded to a carbon atom, forming CR 5 from X 5 to X 7 , and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom is bound by the imidazole ligand from X 5 to X 7 ;

Inventors

  • Hee-Jun Park
  • Ku-Sun Choung
  • Hee-Ryong Kang
  • Kyoung-Jin Park
  • Hyun Kim
  • Ga-Won Lee
  • Seung-hyun Yoon

Assignees

  • LG DISPLAY CO., LTD.

Dates

Publication Date
20260513
Application Date
20211013
Priority Date
20201215

Claims (12)

  1. Organic metal compound with the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L A has the following structure of formula 2; L B is an auxiliary ligand with the following structure of formula 4; m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n equals 3; wherein R1 is an unsubstituted or substituted C1 - C20 alkyl, an unsubstituted alicyclic C4 - C30 group, or an unsubstituted or substituted aromatic C6 - C30 group, and R2 and R3 are independently hydrogen or deuterium, or R1 is as defined above and R2 and R3 form an unsubstituted aromatic C6 - C20 ring; and A has the following structure of formula 3: wherein each of X1 to X4 is independently CR4 ; X5 to X7 is independently CR5 ; X8 to X11 is independently CR6 ; each of R4 to R6 is independently hydrogen, deuterium, or unsubstituted C1 - C20 alkyl; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR4 of X1 to X4 , and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand of X1 to X4 , or an imidazole ligand in formula 2 is bonded to a carbon atom forming CR5 of X5 to X7 , and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand of X5 to X7 ;
  2. Organic metal compound according to Claim 1 , where L A has the following structure of formula 5: where each of R 1 to R 3 and X 1 to X 11 is defined as for Formula 2 and Formula 3.
  3. Organic metal compound according to Claim 1 , where L A has any of the following structures of formula 6A to formula 6F: where each of a, b and c is a number of a substituent; each of R 1 to R 3 is defined as for formula 2; each of R 11 to R 13 is independently hydrogen, deuterium or unsubstituted C 1 -C 20 alkyl.
  4. Organic metal compound according to Claim 1 , where L A has the following structure of formula 7: where each of R 1 to R 3 and X 1 to X 11 is defined as for Formula 2 and Formula 3.
  5. Organic metal compound according to Claim 1 , where L A has the following structure of formula 8A or 8B: where each of d, e and f is a number of a substituent; each of R 1 to R 3 is defined as for formula 2; each of R 11 to R 13 is independently hydrogen, deuterium or unsubstituted C 1 -C 20 alkyl.
  6. Organic metal compound according to any of the preceding claims, wherein the auxiliary ligand L B has the following structure of formula 9A or formula 9B: wherein each of R 21 , R 22 and R 31 to R 33 independently hydrogen , deuterium , unsubstituted or substituted C 1 -C 20 alkyl , unsubstituted or substituted C 1 -C 20 heteroalkyl , unsubstituted or substituted C 2 -C 20 alkenyl , unsubstituted or substituted C 2 -C 20 heteroalkenyl , unsubstituted or substituted C 1 -C 20 alkoxy , amino , a carboxyl group , nitrile , isonitrile , sulfanyl , phosphine , unsubstituted or substituted C 1 -C 20 alkylamino , unsubstituted or substituted C 1 -C 20 alkylsilyl , an unsubstituted or substituted alicyclic C 4 -C 30 group , a unsubstituted or substituted heteroalicyclic C3 - C30 group, an unsubstituted or substituted aromatic C6 - C30 group or an unsubstituted or substituted heteroaromatic C3 - C30 group, or if each of j and k is 2 or more, each of adjacent two of R31 to R33 , adjacent two of R21 and adjacent two of R23 independently forms an unsubstituted or substituted alicyclic C4 - C20 ring, an unsubstituted or substituted heteroalicyclic C3 - C20 ring, an unsubstituted or substituted aromatic C6 - C30 ring or an unsubstituted or substituted heteroaromatic C3 - C30 ring.
  7. Organic metal compound according to Claim 1 , wherein the organic metal compound is selected from the following compounds of formula 10:
  8. Organic metal compound according to Claim 1 , wherein the organic metal compound is selected from the following compounds of formula 11:
  9. Organic light-emitting diode comprising: a first electrode; a second electrode facing the first electrode; and an emission layer arranged between the first and the second electrode and comprising at least one emission material layer, where the at least one emission material layer comprises the organic metal compound according to any of the preceding claims.
  10. Organic light-emitting diode according to Claim 9 , wherein the at least one emission material layer comprises a host and a doping material and wherein the doping material comprises the organic metal compound.
  11. Organic light-emitting diode according to Claim 9 , wherein the emission layer comprises a first emission part arranged between the first and the second electrode, and a second emission part arranged between the first emission part and the second electrode, and a first charge generation layer arranged between the first and the second emission part, wherein the first emission part comprises a first emission material layer and the second emission part comprises a second emission material layer, and wherein the first and/or the second emission material layer comprises the organic metal compound.
  12. Organic light-emitting device comprising: a substrate; and the organic light-emitting diode according to one of the Claims 9 until 11 .

Description

BACKGROUND Technical field The present invention relates to an organic metal compound and in particular to an organic metal compound with excellent luminous efficiency and luminous lifetime, an organic light-emitting diode and an organic light emission device comprising the organic metal compound. Discussion of the state of the art Organic light-emitting diodes (OLEDs), one of the most widely used flat display devices, have come to prominence as a rapidly replacing liquid crystal displays (LCDs). OLEDs can be formed as thin organic films of less than 2000 Å and can implement unidirectional or bidirectional images through electrode configurations. OLEDs can even be formed on flexible, transparent substrates such as plastics, making it easy to create flexible or foldable displays. Furthermore, OLEDs can be driven at lower voltages and offer higher color purity than LCDs. Since fluorescent materials utilize only singlet exciton energy in their luminescence process, state-of-the-art fluorescent materials exhibit low luminescence efficiencies. Phosphorescent materials, in contrast, can exhibit high luminescence efficiencies because they utilize both triplet and singlet exciton energy in their luminescence process. However, metal complexes commonly used as phosphorescent materials have a luminescence lifetime that is too short for commercial applications. Therefore, there remains a need to develop a new compound that can improve both luminescence efficiency and lifetime. EP 3 960 747 A1 describes an organic metal compound and an organic light-emitting diode containing this compound. CN 109651444 A reveals a phosphorescent iridium complex comprising a ligand with an aromatic amine as a functional group. SUMMARY Consequently, it was an object of the present invention to develop a compound, as well as an organic light-emitting diode and an organic light-emitting device comprising the compound, which substantially avoid one or more of the problems in the prior art. In particular, one object of the present invention was to provide an organic metal compound with excellent luminous efficiency and luminous lifetime, an organic light-emitting diode and an organic light emission device comprising the compound. Additional features and aspects are set out in the following description and are partly evident from the description or can be learned by carrying out the invention concepts provided here. Other features and aspects of the invention concept can be realized and achieved through the structure, which is specifically referred to in the written description or which can be derived from it, and the claims thereto, as well as the accompanying drawings. The aforementioned problems underlying the present invention were solved by creating an organic metal compound as defined in independent claim 1, as well as an organic light-emitting diode and an organic light-emitting device comprising the compound. The organic metal compound has the following structure of formula 1: Ir(L A ) m (L B ) n [Formula 1] where L A has the following structure of formula 2; L B is an auxiliary ligand with the following structure of formula 4; m is an integer from 1 to 3 and n is an integer from 0 to 2, where m + n ≥ 3; wherein R1 is an unsubstituted or substituted C1 - C20 alkyl, an unsubstituted alicyclic C4 - C30 group, or an unsubstituted or substituted aromatic C6 - C30 group, and R2 and R3 are independently hydrogen or deuterium, or R1 is as defined above and R2 and R3 form an unsubstituted aromatic C6 - C20 ring; and A has the following structure of formula 3: where each of X 1 to X 4 is independently CR 4 ; X 5 to X 7 is independently CR 5 ; X 8 to X 11 is independently CR 6 ; each R 4 to R 6 is independently hydrogen, deuterium, or unsubstituted C 1 -C 20 alkyl; wherein an imidazole ligand in formula 2 is bonded to a carbon atom forming CR 4 from X 1 to X 4 , and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X 1 to X 4 , or an imidazole ligand in formula 2 is bonded to a carbon atom forming CR 5 from X 5 to X 7 , and an iridium atom in formula 1 is bonded to an atom adjacent to the carbon atom bonded by the imidazole ligand from X 5 to X 7 . It can be either a phenylpyridino-based ligand or an acetylacetonate-based ligand. In a preferred embodiment, the ligand L A in the organic metal compound has the following structure of formula 5: where each of R1 to R3 and X1 to X11 is defined as for formula 2 and formula 3. The imidazole ligand is also preferentially bonded to a carbon atom forming CR4 of X1 to X4 , and the atom adjacent to the carbon atom bonded to the imidazole ligand of X1 to X4 is bonded to the iridium atom in formula 1. In another preferred embodiment, the ligand L A has any of the following structures of formula 6A to formula 6F: where each of a, b and c is a number of a substituent and a is an integer from 0 to 2, b is an integer from 0 to 3 and c is an integ