US2021280804A1PendingUtilityA1
Organic electroluminescent materials and devices
Est. expiryMar 6, 2040(~13.6 yrs left)· nominal 20-yr term from priority
C09K 2211/185C09K 11/06H10K 85/658H10K 85/633H10K 85/624H10K 85/6574H10K 85/626H10K 85/622H10K 85/657H10K 85/654C07B 2200/05C07F 15/0033C07F 15/0086C09K 11/02C09K 2211/1048C09K 2211/1044C09K 2211/1007C09K 2211/1014H01L 51/0087H01L 51/5012H10K 85/6576H10K 85/346H10K 50/12H10K 85/6572H10K 85/615H10K 85/342H10K 85/40H10K 50/11H10K 2101/10
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Claims
Abstract
Provided are novel metal complexes comprising tetradentate pyrimidine and pyrazine ligands. The organometallic compounds can have the structure ofthat are useful as emitters in OLEDs and when used in OLEDs provides improved device performance. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of
wherein:
each of X 1 and X 2 is independently C or N, with at least one being N;
each of X 3 , X 4 , and X 5 is independently C or N;
at least one of X 3 , X 4 , and X 5 is C and at least one is N;
L 1 and L 2 are linkers that can be present, with at least one of them being present and each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, BR, BRR′, NR, alkyl, cycloalkyl, aryl, and heteroaryl when present;
R A , R B , R C , and R D each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M is Pt, Pd, Au, Ag, Cu or Zn; and
any two adjacent R, R′, R A , R B , R C , and R D can be joined or fused together to form a ring,
with the proviso that the compound is not the one shown below:
2 . The compound of claim 1 , wherein each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
3 . The compound of claim 1 , wherein one of X 1 and X 2 is N, and the other is C.
4 . The compound of claim 1 , wherein one of X 3 , X 4 , and X 5 is N, and the remaining ones of X 3 , X 4 , and X5 are C.
5 . The compound of claim 1 , wherein one of L 1 and L 2 is present, and the other is not present.
6 . The compound of claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of O, S, CRR′, SiRR′, and NR when present.
7 . The compound of claim 1 , wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof.
8 . The compound of claim 1 , wherein at least one pair of two adjacent R A , R B , R C , and R D are joined or fused together to form a 5-membered or 6-membered aromatic ring.
9 . The compound of claim 8 , wherein the 5-membered or 6-membered aromatic ring is selected from the group consisting of benzene, pyridine, pyrimidine, pyridazine, pyrazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, or thiazole.
10 . The compound of claim 8 , wherein the 5-membered or 6-membered aromatic ring is further fused to form a multiple fused ring system
11 . The compound of claim 1 , wherein at least one of R A , R B , R C , and R D is Selected from the Group Consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
12 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
13 . The compound of claim 1 , wherein L 1 or L 2 is independently O, CRR′, SiRR′, or NR.
14 . The compound of claim 12 , wherein two adjacent R A , R B , R C , and R D are joined or fused together to form a 5-membered or 6-membered aromatic ring.
15 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
16 . The compound of claim 1 , wherein the compound is selected from the group consisting of:
Compound 1-1, Compound 1-2,
Compound 1-3, and Compound 1-4
having the following structure
wherein,
in Compound 1-1, L 2 = NPh,
in Compound 1-2, L 2 = O,
in Compound 1-3, L 2 = CMe 2 , and
in Compound 1-4 L 2 = SiPh 2 ,
Compound 2-1, Compound 2-2,
Compound 2-3, and Compound 2-4
having the following structure
wherein,
in Compound 2-1, L 2 = Ph,
in Compound 2-2, L 2 = O,
in Compound 2-3, L 2 = CMe 2 , and
in Compound 2-4, L 2 = SiPh 2 .,
Compound 3-1, Compound 3-2,
Compound 3-3, and Compound 3-4
having the following structure
wherein,
in Compound 3-1, L 2 = Ph,
in Compound 3-2, L 2 = O,
in Compound 3-3, L 2 = CMe 2 , and
in Compound 3-4, L 2 = SiPh 2 .,
Compound 4-1, Compound 4-2,
Compound 4-3, and Compound 4-4
having the following structure
wherein.
in Compound 4-1, L 2 = NPh,
in Compound 4-2, L 2 = O,
in Compound 4-3, L 2 = CMe 2 , and
in Compound 4-4, L 2 = SiPh 2 .,
Compound 5-1, Compound 5-2,
Compound 5-3, and Compound 5-4
having the following structure
wherein,
in Compound 5-1, L 2 = NPh,
in Compound 5-2, L 2 = O,
in Compound 5-3, L 2 = CMe 2 , and
in Compound 5-4 L 2 = SiPh 2 .,
Compound 6-1, Compound 6-2,
Compound 6-3, and Compound 6-4
having the following structure
wherein,
in Compound 6-1, L 2 = Ph,
in Compound 6-2, L 2 = O,
in Compound 6-3, L 2 = CMe 2 , and
in Compound 6-4, L 2 = SiPh 2 .,
Compound 7-1, Compound 7-2,
Compound 7-3, and Compound 7-4
having the following structure
wherein,
in Compound 7-1, L 2 = Ph,
in Compound 7-2, L 2 = O,
in Compound 7-3, L 2 = CMe 2 , and
in Compound 7-4, L 2 = SiPh 2 .,
Compound 8-1, Compound 8-2,
Compound 8-3, and Compound 8-4
having the following structure
wherein.
in Compound 8-1, L 2 = NPh,
in Compound 8-2, L 2 = O,
in Compound 8-3, L 2 = CMe 2 , and
in Compound 8-4, L 2 = SiPh 2 .,
Compound 9-1, Compound 9-2,
Compound 9-3, and Compound 9-4
having the following structure
wherein,
in Compound 9-1, L 2 = NPh,
in Compound 9-2, L 2 = O,
in Compound 9-3, L 2 = CMe 2 , and
in Compound 9-4, L 2 = SiPh 2 .,
Compound 11-1, Compound 11-2,
Compound 11-3, and Compound 11-4
having the following structure
wherein,
in Compound 11-1, L 2 = NPh,
in Compound 11-2, L 2 = O,
in Compound 11-3, L 2 = CMe 2 , and
in Compound 11-4, L 2 = SiPh 2 .,
Compound 12-1, Compound 12-2,
Compound 12-3, and Compound 12-4
having the following structure
wherein,
in Compound 12-1, L 2 = NPh,
in Compound 12-2, L 2 = O,
in Compound 12-3, L 2 = CMe 2 , and
in Compound 12-4, L 2 = SiPh 2 .,
Compound 13-1, Compound 13-2,
Compound 13-3, and Compound 13-4
having the following structure
wherein,
in Compound 13-1, L 2 = NPh,
in Compound 13-2, L 2 = O,
in Compound 13-3, L 2 = CMe 2 , and
in Compound 13-4, L 2 = SiPh 2 .,
Compound 14-1, Compound 14-2,
Compound 14-3, and Compound 14-4
having the following structure
wherein,
in Compound 14-1, L 2 = NPh,
in Compound 14-2, L 2 = O,
in Compound 14-3, L 2 = CMe 2 , and
in Compound 14-4, L 2 = SiPh 2 .,
Compound 15-1, Compound 15-2,
Compound 15-3, and Compound 15-4
having the following structure
wherein,
in Compound 15-1, L 2 = NPh,
in Compound 15-2, L 2 =O,
in Compound 15-3, L 2 = CMe 2 , and
in Compound 15-4 L 2 = SiPh 2 .,
Compound 16-1, Compound 16-2,
Compound 16-3, and Compound 16-4,
having the following structure
wherein,
in Compound 16-1, L 2 = NPh,
in Compound 16-2, L 2 = O,
in Compound 16-3, L 2 = CMe 2 , and
in Compound 16-4, L 2 = SiPh 2 .,
Compound 17-1, Compound 17-2,
Compound 17-3, and Compound 17-4
having the following structure
wherein,
in Compound 17-1, L 2 = NPh,
in Compound 17-2, L 2 = O,
in Compound 17-3, L 2 = CMe 2 , and
in Compound 17-4, L 2 = SiPhd 2 .,
Compound 18-1, Compound 18-2,
Compound 18-3, and Compound 18-4
having the following structure
wherein,
in Compound 18-1, L 2 = NPh,
in Compound 18-2, L 2 = O,
in Compound 18-3, L 2 = CMe 2 , and
in Compound 18-4, L 2 = SiPh 2 .,
Compound 19-1, Compound 19-2,
Compound 19-3, and Compound 19-4
having the following structure
wherein,
in Compound 19-1, L 2 = NPh,
in Compound 19-2, L 2 = O,
in Compound 19-3, L 2 = CMe 2 , and
in Compound 19-4, L 2 = SiPh 2 .,
Compound 20-1, Compound 20-2,
Compound 20-3, and Compound 20-4
having the following structure
wherein,
in Compound 20-1, L 2 = NPh,
in Compound 20-2, L 2 = O,
in Compound 20-3, L 2 = CMe 2 , and
in Compound 20-4, L 2 = SiPh 2 .,
Compound 21-1, Compound 21-2,
Compound 21-3, and Compound 21-4
having the following structure
wherein,
in Compound 21-1, L 2 = NPh,
in Compound 21-2, L 2 = O,
in Compound 21-3, L 2 = CMe 2 , and
in Compound 21-4, L 2 = SiPh 2 .,
Compound 25-1, Compound 25-2,
Compound 25-3, and Compound 25-4
having the following structure
wherein,
in Compound 25-1, L 2 = NPh,
in Compound 25-2, L 2 = O,
in Compound 25-3, L 2 = CMe 2 , and
in Compound 25-4, L 2 = SiPh 2 .,
Compound 26-1, Compound 26-2,
Compound 26-3, and Compound 26-4
having the following structure
wherein,
in Compound 26-1, L 2 = NPh,
in Compound 26-2, L 2 = O,
in Compound 26-3, L 2 = CMe 2 , and
in Compound 26-4, L 2 = SiPh 2 .,
Compound 27-1, Compound 27-2,
Compound 27-3, and Compound 27-4
having the following structure
wherein,
in Compound 27-1, L 2 = NPh,
in Compound 27-2, L 2 = O,
in Compound 27-3, L 2 = CMe 2 , and
in Compound 27-4, L 2 = SiPh 2 .,
Compound 28-1, Compound 28-2,
Compound 28-3, and Compound 28-4
having the following structure
wherein,
in Compound 28-1, L 2 = NPh,
in Compound 28-2, L 2 = O,
in Compound 28-3, L 2 = CMe 2 , and
in Compound 28-4, L 2 = SiPh 2 .,
Compound 29-1, Compound 29-2,
Compound 29-3, and Compound 29-4
having the following structure
wherein,
in Compound 29-1, L 2 = NPh,
in Compound 29-2, L 2 = O,
in Compound 29-3, L 2 = CMe 2 , and
in Compound 29-4, L 2 = SiPh 2 .,
Compound 31-1, Compound 31-2,
Compound 31-3, and Compound 31-4
having the following structure
wherein,
in Compound 31-1, L 2 = NPh,
in Compound 31-2, L 2 = O,
in Compound 31-3, L 2 = CMe 2 , and
in Compound 31-4, L 2 = SiPh 2 .,
Compound 32-1, Compound 32-2,
Compound 32-3, and Compound 32-4
having the following structure
wherein,
in Compound 32-1, L 2 = NPh,
in Compound 32-2, L 2 = O,
in Compound 32-3, L 2 = CMe 2 , and
in Compound 32-4, L 2 = SiPh 2 .,
Compound 33-1, Compound 33-2,
Compound 33-3, and Compound 33-4
having the following structure
wherein,
in Compound 33-1, L 2 = NPh,
in Compound 33-2, L 2 = O,
in Compound 33-3, L 2 = CMe 2 , and
in Compound 33-4, L 2 = SiPh 2 .,
Compound 34-1, Compound 34-2,
Compound 34-3, and Compound 34-4
having the following structure
wherein,
in Compound 34-1, L 2 = NPh,
in Compound 34-2, L 2 = O,
in Compound 34-3, L 2 = CMe 2 , and
Compound 34-4, L 2 in = SiPh 2 .,
Compound 36-1, Compound 36-2,
Compound 36-3, and Compound 36-4
having the following structure
wherein,
in Compound 36-1, L 2 = NPh,
in Compound 36-2, L 2 = O,
in Compound 36-3, L 2 = CMe 2 , and
in Compound 36-4, L 2 = SiPh 2 .,
Compound 37-1, Compound 37-2,
Compound 37-3, and Compound 37-4
having the following structure
wherein,
in Compound 37-1, L 2 = NPh,
in Compound 37-2, L 2 = O,
in Compound 37-3, L 2 = CMe 2 , and
in Compound 37-4, L 2 = SiPh 2 .,
Compound 38-1, Compound 38-2,
Compound 38-3, and Compound 38-4
having the following structure
wherein,
in Compound 38-1, L 2 = NPh,
in Compound 38-2, L 2 = O,
in Compound 38-3, L 2 = CMe 2 , and
in Compound 38-4, L 2 = SiPh 2 .,
Compound 39-1, Compound 39-2,
Compound 39-3, and Compound 39-4
having the following structure
wherein,
in Compound 39-1, L 2 = NPh,
in Compound 39-2, L 2 = O,
in Compound 39-3, L 2 = CMe 2 , and
in Compound 39-4, L 2 = SiPh 2 .,
Compound 40-1, Compound 40-2,
Compound 40-3, and Compound 40-4
having the following structure
wherein,
in Compound 40-1, L 2 = NPh,
in Compound 40-2, L 2 = O,
in Compound 40-3, L 2 = CMe 2 , and
in Compound 40-4, L 2 = SiPh 2 .,
Compound 40-1, Compound 40-2,
Compound 40-3, and Compound 40-4
having the following structure
wherein,
in Compound 41-1, L 2 = NPh,
in Compound 41-2, L 2 = O,
in Compound 41-3, L 2 = CMe 2 , and
in Compound 41-4, L 2 = SiPh 2 .,
Compound 42-1, Compound 42-2,
Compound 42-3, and Compound 42-4
having the following structure
wherein,
in Compound 42-1, L 2 = NPh,
in Compound 42-2, L 2 = O,
in Compound 42-3, L 2 = CMe 2 , and
in Compound 42-4, L 2 = SiPh 2 .,
Compound 43-1, Compound 43-2,
Compound 43-3, and Compound 43-4
having the following structure
wherein,
in Compound 43-1, L 2 = NPh,
in Compound 43-2, L 2 = O,
in Comound 43-3, L 2 = CMe 2 , and
in Compound 43-4, L 2 = SiPh 2 ., and
Compound 44-1, Compound 44-2
Compound 44-3, and Compound 44-4
having the following structure
wherein,
in Compound 44-1, L 2 = NPh,
in Compound 44-2, L 2 = O,
in Compound 44-3, L 2 = CMe 2 , and
in Compound 44-4, L 2 = SiPh 2 ..
17 . 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 of
wherein:
each of X 1 and X 2 is independently C or N, with at least one being N;
each of X 3 , X 4 , and X 5 is independently C or N;
at least one of X 3 , X 4 , and X 5 is C and at least one is N;
L 1 and L 2 are linkers that can be present, with at least one of them being present and each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, BR, BRR′, NR, alkyl, cycloalkyl, aryl, and heteroaryl when present;
R A , R B , R C , and R D each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M is Pt, Pd, Au, Ag, Cu or Zn; and
any two adjacent R, R′, R A , R B , R C , and R D can be joined or fused together to form a ring,
with the proviso that the compound is not the one shown below:
18 . The OLED of claim 17 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).
19 . The OLED of claim 18 , wherein the host is selected from the group consisting of:
and combinations thereof.
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 of
wherein:
each of X 1 and X 2 is independently C or N, with at least one being N;
each of X 3 , X 4 , and X 5 is independently C or N;
at least one of X 3 , X 4 , and X 5 is C and at least one is N;
L 1 and L 2 are linkers that can be present, with at least one of them being present and each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, GeRR′, BR, BRR′, NR, alkyl, cycloalkyl, aryl, and heteroaryl when present;
R A , R B , R C , and R D each independently represents zero, mono, or up to the maximum allowed number of substitutions to its associated ring;
each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
M is Pt, Pd, Au, Ag, Cu or Zn; and
any two adjacent R, R′, R A , R B , R C , and R D can be joined or fused together to form a ring,
with the proviso that the compound is not the one shown below:Join the waitlist — get patent alerts
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