Organic electroluminescent materials and devices
A novel compound is disclosed which includes a ligand L A of Formula II, wherein: ring B is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; X 1 to X 4 are each independently selected from the group consisting of C, N, and CR; at least two adjacent ones of X 1 , X 2 , X 3 , and X 4 are CR and fused into a five or six-membered aromatic ring R 3 represents zero, mono, or up to a maximum allowed substitutions to its associated ring; each R, R 1 , and R 3 is independently hydrogen or a General Substituent defined herein; R 2 is a General Substituent defined herein; and two substituents can be joined or fused to form a ring; the ligand L A is complexed to a metal M through the two indicated dash lines of each Formula; and the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.
1 . A compound comprising a ligand L A of Formula II, Formula III, or Formula IV:
wherein:
ring B is a 6-membered aryl or heteroaryl ring;
X 1 to X 4 are each independently selected from the group consisting of C, N, and CR;
at least one pair of adjacent X 1 to X 4 are each C and fused to a structure of Formula V
where indicated by “ ”;
X 5 to X 12 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″;
R B and R C each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each R B , R C , R, R′, R″, and, when present, R b 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 L A and L B are complexed to a metal M through the two indicated dash lines of each Formula; and
when L A has a structure of Formula II,
the compound has a formula of M(L A ) p (L C ) r , wherein p is 1 or 2; r is 1 or 2; and p+r is the oxidation state of the metal M; and L C comprises a structure of
at least one R B 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 R a and R c is independently alkyl.
2 . The compound of claim 1 , wherein each of R B , R C , R, R′, and R″ is independently hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof; and
when L A has a structure of Formula II, at least one R B 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, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.
3 . The compound of claim 1 , wherein L A has a structure of Formula III and at least one of X 1 to X 4 is N.
4 . The compound of claim 1 , wherein each of X 5 to X 12 is C.
5 . The compound of claim 1 , wherein R B is hydrogen or independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof; and
when L A has a structure of Formula II, at least one R B of the ring bonded to ring A is a substituent selected from the group consisting of alkyl having 3 to 15 carbon atoms, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.
6 . The compound of claim 1 , wherein at least one R C is independently an alkyl or cycloalkyl group.
7 . The compound of claim 1 , wherein L A has a structure of Formula IV and at least one of X 1 to X 4 is N.
8 . The compound of claim 1 , wherein the metal M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.
9 . The compound of claim 1 , wherein the compound comprises the ligand L A selected from the group consisting of:
wherein each of R B can be the same or different, each of R C can be the same or different, and
R B and R C for each occurrence is independently selected from 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.
10 . The compound of claim 1 , wherein at least one R C is selected from the group consisting of:
11 . The compound of claim 1 , wherein L A has a structure of Formula III or Formula IV, and the compound has a formula of M(L A ) p (L B ) q (L C ) r wherein L B and L C are each a bidentate ligand; and wherein p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p+q+r is the oxidation state of the metal M.
12 . The compound of claim 11 , wherein L B and L C are each independently selected from the group consisting of:
wherein:
each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen; Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
R e and R f can be fused or joined to form a ring;
each R a , R b , R c , and R d independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and
two adjacent substituents of R a , R b , R c , and R d can be fused or joined to form a ring or form a multidentate ligand.
13 . The compound of claim 11 , wherein M is Ir, p is 1 or 2, and at least one of L B or L C is present and is a substituted or unsubstituted acetylacetonate ligand.
14 . The compound of claim 1 , wherein ligand L A has a structure of Formula II.
15 . The compound of claim 14 , wherein R B para to the metal bond comprises silyl, amino, boryl, or alkyl comprising 3 to 15 carbon atoms.
16 . The compound of claim 1 , wherein the compound is selected from the group consisting of
17 . The compound of claim 1 , wherein ligand L A has a structure of Formula III or Formula IV.
18 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the following structures:
19 . 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 L A of Formula II, Formula III, or Formula IV:
wherein:
ring B is a 6-membered aryl or heteroaryl ring;
X 1 to X 4 are each independently selected from the group consisting of C, N, and CR;
at least one pair of adjacent X 1 to X 4 are each C and fused to a structure of Formula V
where indicated by “ ”;
X 5 to X 12 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″;
R B and R C each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each R B , R C , R, R′, R″, and, when present, R b 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 L A and L B are complexed to a metal M through the two indicated dash lines of each Formula; and
when L A has a structure of Formula II,
the compound has a formula of M(L A ) p (L C ) r , wherein p is 1 or 2; r is 1 or 2; and p+r is the oxidation state of the metal M; and L C comprises a structure of
at least one R B 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 R a and R c is independently alkyl.
20 . 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 L A of Formula II, Formula III, or Formula IV:
wherein:
ring B is a 6-membered aryl or heteroaryl ring;
X 1 to X 4 are each independently selected from the group consisting of C, N, and CR;
at least one pair of adjacent X 1 to X 4 are each C and fused to a structure of Formula V
where indicated by “ ”;
X 5 to X 12 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″;
R B and R C each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each R B , R C , R, R′, R″, and, when present, R b 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 L A and L B are complexed to a metal M through the two indicated dash lines of each Formula; and
when L A has a structure of Formula II,
the compound has a formula of M(L A ) p (L C ) r , wherein p is 1 or 2; r is 1 or 2; and p+r is the oxidation state of the metal M; and L C comprises a structure of
at least one R B 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 R a and R c is independently alkyl.