US 12,247,150 B2
Organic electroluminescent materials and devices
Jui-Yi Tsai, Newtown, PA (US); Chuanjun Xia, Lawrenceville, NJ (US); Chun Lin, Yardley, PA (US); Adrian U. Palacios, Saragossa (ES); Enrique Oñate, Saragossa (ES); Miguel A. Esteruelas, Saragossa (ES); Pierre-Luc T. Boudreault, Pennington, NJ (US); Sonia Bajo, Saragossa (ES); and Montserrat Oliván, Saragossa (ES)
Assigned to UNIVERSAL DISPLAY CORPORATION, Ewing, NJ (US)
Filed by Universal Display Corporation, Ewing, NJ (US)
Filed on May 1, 2023, as Appl. No. 18/309,992.
Application 16/563,832 is a division of application No. 15/866,561, filed on Jan. 10, 2018, granted, now 10,457,864, issued on Oct. 29, 2019.
Application 18/309,992 is a continuation of application No. 17/373,169, filed on Jul. 12, 2021, granted, now 11,692,132.
Application 17/373,169 is a continuation of application No. 16/563,832, filed on Sep. 7, 2019, granted, now 11,098,245, issued on Aug. 24, 2021.
Application 15/866,561 is a continuation in part of application No. 15/407,337, filed on Jan. 17, 2017, abandoned.
Claims priority of provisional application 62/293,100, filed on Feb. 9, 2016.
Claims priority of provisional application 62/338,616, filed on May 19, 2016.
Prior Publication US 2023/0287263 A1, Sep. 14, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C09K 11/06 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC C09K 11/06 (2013.01) [C07F 15/0033 (2013.01); H10K 85/342 (2023.02); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/12 (2023.02); H10K 85/626 (2023.02); H10K 85/631 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. A compound having a formula M(LA)x(LB)y:
wherein the ligand LA is selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein the ligand LB is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, or 2;
wherein y is 1, or 2;
wherein x+y is the oxidation state of the metal M;
wherein LA is different from LB, and when x or y is larger than 1, each plurality of LA, or LB are also different;
wherein each X1 to X17 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Ra may represent from mono substitution up to the maximum possible number of substitutions, or no substitution;
wherein R′, R″, Ra, Rb, Rc, and Ra 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, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Ra are optionally joined or fused to form a ring, and wherein any two substituents of Ra, Rb, Rc, and Ra are optionally joined or fused to form a tetradentate or hexadentate ligand.
 
16. An organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(LA)x(LB)y:
wherein the ligand LA is selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein the ligand LB is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, or 2;
wherein y is 1, or 2;
wherein x+y is the oxidation state of the metal M;
wherein LA is different from LB, and when x or y is larger than 1, each plurality of LA, or LB are also different;
wherein each X1 to X17 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Ra may represent from mono substitution up to the maximum possible number of substitutions, or no substitution;
wherein R′, R″, Ra, Rb, Rc, and Ra 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, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Ra are optionally joined or fused to form a ring, and wherein any two substituents of Ra, Rb, Rc, and Ra are optionally joined or fused to form a tetradentate or hexadentate ligand.
 
19. A consumer product, comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula M(LA)x(LB)y:
wherein the ligand LA is selected from the group consisting of:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein the ligand LB is selected from the group consisting of:

OG Complex Work Unit Chemistry
wherein M is a metal having an atomic number greater than 40;
wherein x is 1, or 2;
wherein y is 1, or 2;
wherein x+y is the oxidation state of the metal M;
wherein LA is different from LB, and when x or y is larger than 1, each plurality of LA, or LB are also different;
wherein each X1 to X17 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C—O, S═O, SO2, CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Ra may represent from mono substitution up to the maximum possible number of substitutions, or no substitution;
wherein R′, R″, Ra, Rb, Rc, and Ra 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, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Ra are optionally joined or fused to form a ring, and wherein any two substituents of Ra, Rb, Rc, and Ra are optionally joined or fused to form a tetradentate or hexadentate ligand.