US2023209990A1PendingUtilityA1
Organic electroluminescent materials and devices
Est. expirySep 3, 2035(~9.1 yrs left)· nominal 20-yr term from priority
Inventors:Bin MaVadim AdamovichEdward BarronJui-Yi TsaiMingjuan SuLech MichalskiiChuanjun XiaMichael S. WeaverWalter YeagerBert Alleyne
H10K 50/11C07F 15/0033C09K 11/06H10K 85/654H10K 85/342C09K 11/025C09K 2211/185H10K 85/6576C09K 2211/1029Y02E10/549H10K 2101/10H10K 85/6572H10K 85/657H10K 85/40H10K 85/615H10K 85/626H10K 85/622
83
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
A compound having a formula (L A ) m Ir(L B ) 3-m having a structure selected from is disclosed. In the structures of formula (L A ) m Ir(L B ) 3-m , m is 1 or 2, R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from hydrogen, deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof, and, R 6 is selected from C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof.
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A compound having a formula M(L A ) h (L B ) y (L C ) z :
wherein the ligand L A , L B , and L C are each independently selected from the group consisting of:
wherein each X 1 to X 13 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, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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;
wherein any two adjacent substitutents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand;
wherein M is a metal having an atomic mass greater than 40;
wherein h is 1 or 2;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M; and
wherein a molecule of the compound has an orientation factor value greater than 0.67.
2 . The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.
3 . The compound of claim 1 , wherein one of R a , R b , R c , and R d is a mono substituent having at least thirteen carbon atoms, and all the rest of R a , R b , R c , and R d has maximum carbon number of six.
4 . The compound of claim 1 , wherein each X 1 to X 13 are carbon.
5 . The compound of claim 1 , wherein the compound has the formula Ir(L A ) 2 (L B ).
6 . The compound of claim 10 , wherein L A has the formula selected from the group consisting of:
wherein L B has the formula:
7 . The compound of claim 5 , wherein L A and L B are different and each independently selected from the group consisting of:
8 . The compound of claim 5 , wherein L A and L B are each independently selected from the group consisting of:
9 . The compound of claim 1 , wherein the compound has the formula of Pt(L A )(L B ), wherein L A and L B are different.
10 . The compound of claim 1 , wherein the compound having a formula (L A ) m Ir(L B ) 3-m having a structure selected from the group consisting of
wherein m is 1 or 2;
wherein R 1 , R 2 , R 4 , and R 5 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 3 represents mono, di, or tri substitution, or no substitution;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen, deuterium, C1 to C6 alkyl, C1 to C6 cycloalkyl, and partially or fully deuterated or fluorinated variants thereof; and
wherein R 6 is selected from the group consisting of alkyl having at least seven carbon atoms, cycloalkyl having at least seven carbon atoms, alkyl-cycloalkyl having at least seven carbon atoms, and partially or fully deuterated or fluorinated variants thereof.
11 . The compound of claim 10 , wherein R 6 is selected from the group consisting of alkyl having at least eight carbon atoms, cycloalkyl having at least eight carbon atoms, alkyl-cycloalkyl having at least eight carbon atoms, and partially for fully deuterated or fluorinated variants thereof.
12 . The compound of claim 10 , wherein L A is selected from the group consisting of:
13 . The compound of claim 10 , wherein L B is selected from the group consisting of:
14 . The compound of claim 12 , wherein the compound is Compound x having the formula Ir(L Aj ) 2 (L Bk );
wherein x=227j+k−227, j is an integer from 1 to 225, and k is an integer from 1 to 227; wherein L B1 to L B227 has the following structures:
15 . A compound having a formula (L A ) m Ir(L B ) 3-m having a structure selected from the group consisting of:
wherein m is 1 or 2;
wherein R 1 , R 2 , R 4 , and R 5 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 3 represents mono, di, or tri substitution, or no substitution;
wherein R 6 represents mono substitution, or no substitution; and
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, partially or fully deuterated or fluorinated variants thereof, and combinations thereof.
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 selected from the group consisting of M(L A ) h (L B ) y (L C ) z ,
wherein m is 1 or 2;
wherein the ligand L A , L B , and L C are each independently selected from the group consisting of:
wherein each X 1 to X 13 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, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d 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;
wherein any two adjacent substitutents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand;
wherein M is a metal having an atomic mass greater than 40;
wherein h is 1 or 2;
wherein y is 0, 1, or 2;
wherein z is 0, 1, or 2;
wherein x+y+z is the oxidation state of the metal M;
wherein a molecule of M(L A ) h (L B ) y (L C ) z , has an orientation factor value greater than 0.67;
wherein R 1 , R 2 , R 4 , and R 5 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 3 represents mono, di, or tri substitution, or no substitution;
wherein R 6 represents mono substitution, or no substitution; and
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, partially or fully deuterated or fluorinated variants thereof, and combinations thereof.
17 . The OLED of claim 16 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.
18 . The OLED of claim 16 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
19 . The OLED of claim 16 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
20 . The OLED of claim 16 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:
combinations thereof.Join the waitlist — get patent alerts
Track US2023209990A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.