US 12,723,193 B2Granted

Organic electroluminescent materials and devices

AssigneeUniversal Display Corporation

InventorsPierre-Luc T. Boudreault, Bert Alleyne, Zhiqiang Ji

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Abstract

A novel compound is disclosed which includes a ligand LA of Formula II, wherein: ring B is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; X1 to X4 are each independently selected from the group consisting of C, N, and CR; at least two adjacent ones of X1, X2, X3, and X4 are CR and fused into a five or six-membered aromatic ring R3 represents zero, mono, or up to a maximum allowed substitutions to its associated ring; each R, R1, and R3 is independently hydrogen or a General Substituent defined herein; R2 is a General Substituent defined herein; and two substituents can be joined or fused to form a ring; the ligand LA is complexed to a metal M through the two indicated dash lines of each Formula; and the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

Claims20

Dependent claims

A compound comprising a ligand LA of Formula II, Formula III, or Formula IV:

wherein:
ring B is a 6-membered aryl or heteroaryl ring;
X1 to X4 are each independently selected from the group consisting of C, N, and CR;
at least one pair of adjacent X1 to X4 are each C and fused to a structure of Formula V
where indicated by “”;
X5 to X12 are each independently C or N;
Z is selected from the group consisting of O, S, Se, NR′, SiR′R″, and GeR′R″;
Y is selected from the group consisting of O, S, Se, NR′, CR′R″, SiR′R″, and GeR′R″;
RB and RC each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each RB, RC, R, R′, R″, and, when present, Rb is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
and two substituents can be joined or fused to form a ring;
the ligands LA and LB are complexed to a metal M through the two indicated dash lines of each Formula;
and
when LA has a structure of Formula II,
the compound has a formula of M(LA)p(LC)r, wherein p is 1 or 2;
r is 1 or 2;
and p+r is the oxidation state of the metal M;
and LC comprises a structure of
at least one RB of the ring bonded to ring A is a substituent selected from the group consisting of alkyl having 3 to 15 carbon atoms, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof;
and
each of Ra and Rc is independently alkyl.

18 more elements

An organic light emitting device (OLED) comprising:

an anode;
a cathode;
and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand LA of Formula II, Formula III, or Formula IV:
wherein:
ring B is a 6-membered aryl or heteroaryl ring;
X1 to X4 are each independently selected from the group consisting of C, N, and CR;
at least one pair of adjacent X1 to X4 are each C and fused to a structure of Formula V
where indicated by “”;
X5 to X12 are each independently C or N;
Z is selected from the group consisting of O, S, Se, NR′, SiR′R″, and GeR′R″;
Y is selected from the group consisting of O, S, Se, NR′, CR′R″, SiR′R″, and GeR′R″;
RB and RC each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each RB, RC, R, R′, R″, and, when present, Rb is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
and two substituents can be joined or fused to form a ring;
the ligands LA and LB are complexed to a metal M through the two indicated dash lines of each Formula;
and
when LA has a structure of Formula II,
the compound has a formula of M(LA)p(LC)r, wherein p is 1 or 2;
r is 1 or 2;
and p+r is the oxidation state of the metal M;
and LC comprises a structure of
at least one RB of the ring bonded to ring A is a substituent selected from the group consisting of alkyl having 3 to 15 carbon atoms, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof;
and
each of Ra and Rc is independently alkyl.

22 more elements

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, wherein the organic layer comprises a compound comprising a ligand LA of Formula II, Formula III, or Formula IV:
wherein:
ring B is a 6-membered aryl or heteroaryl ring;
X1 to X4 are each independently selected from the group consisting of C, N, and CR;
at least one pair of adjacent X1 to X4 are each C and fused to a structure of Formula V
where indicated by “”;
X5 to X12 are each independently C or N;
Z is selected from the group consisting of O, S, Se, NR′, SiR′R″, and GeR′R″;
Y is selected from the group consisting of O, S, Se, NR′, CR′R″, SiR′R″, and GeR′R″;
RB and RC each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each RB, RC, R, R′, R″, and, when present, Rb is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof;
and two substituents can be joined or fused to form a ring;
the ligands LA and LB are complexed to a metal M through the two indicated dash lines of each Formula;
and
when LA has a structure of Formula II,
the compound has a formula of M(LA)p(LC)r, wherein p is 1 or 2;
r is 1 or 2;
and p+r is the oxidation state of the metal M;
and LC comprises a structure of
at least one RB of the ring bonded to ring A is a substituent selected from the group consisting of alkyl having 3 to 15 carbon atoms, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof;
and
each of Ra and Rc is independently alkyl.

22 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/352,064Filed 13 Jul 2023 · continuation
Priority: 3 Oct 2016
Published: US 2023/0363252 A19 Nov 2023
Granted: 1 Sep 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
C07F 15/0033
Compounds of the platinum group: iridium compounds
H10K 85/342
Transition metal complexes, e.g. Rupolypyridine complexes: comprising iridium
C09K 2211/1011
Carbocyclic compounds: condensed systems

Family

Application62/403,424Us provisional application · filed 3 Oct 2016
Application15/706,186Parent of this continuation-in-part · filed 15 Sep 2017
Application15/825,297Parent of this continuation-in-part · filed 29 Nov 2017
Application15/950,351Parent of this continuation-in-part · filed 11 Apr 2018
Application16/375,467Parent of this continuation-in-part · filed 4 Apr 2019
Application62/930,837Us provisional application · filed 5 Nov 2019
Application16/828,080Parent of this continuation · filed 24 Mar 2020
Application17/343,138Parent of this continuation · filed 9 Jun 2021
US 11,081,658 B2Parent of this continuation · filed 3 Aug 2021
US 11,127,906 B2Parent of this continuation-in-part · filed 21 Sep 2021
US 11,183,642 B2Parent of this continuation-in-part · filed 23 Nov 2021
US 11,189,804 B2Parent of this continuation-in-part · filed 30 Nov 2021
US 11,196,010 B2Parent of this continuation-in-part · filed 7 Dec 2021
US 2023/0363252 A1Pre-grant publication · published 9 Nov 2023
US 11,711,969 B2Parent of this continuation
Application16/828,080Parent of this continuation-in-part
US 2018/0097179 A1Published application
US 2018/0097187 A1Published application
US 2018/0240988 A1Published application
US 2019/0237683 A1Published application
US 2020/0227659 A1Published application
US 2022/0367821 A1Published application
US 12,723,193 B2This patent

From the US filing history. Foreign family members aren’t listed.