Organic electroluminescent materials and devices
This invention discloses a novel two dimensional material having propellane core for organic light emitting diodes. These compounds can be used as hosts, charging transporting materials, or blocking materials for PHOLEDs. The devices comprising these compounds have better performance due to the honeycomb pi-extended structure in the propellane molecules.
1. A compound comprising a [n 1 .n 2 .n 3 ]propellane of Formula I:
wherein L 1 comprises a carbon chain having (n 1 -2) carbon atoms, L 2 comprises a carbon chain having (n 2 -2) carbon atoms, and L 3 comprises a carbon chain having (n 3 -2) carbon atoms;
wherein n 1 , n 2 , and n 3 are each independently an integer of 3 or 4;
wherein C 11 -L 1 -C 1n1 forms a first conjugated ring system, C 21 -L 2 -C 2n2 forms a second conjugated ring system, and C 31 -L 3 -C 3n3 forms a third conjugated ring system;
wherein C 31 -L 3 -C 3n3 is selected from the group consisting of:
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;
wherein R and R′ are optionally fused or joined to form a ring;
wherein the first, second and third conjugated ring systems are each optionally further substituted by one or more substituents selected from the group consisting of deuterium, halogen, 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, and combinations thereof;
wherein any two adjacent substituents are optionally fused or joined to form a ring; and
with the proviso that when the first, second and third conjugated ring systems are each a naphthalene as shown in the following structure:
at least one of the first, second and third conjugated ring systems is substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein any two adjacent substituents are optionally fused or joined to form a 5-member hetero-aromatic ring; and
with the proviso that Formula I comprises at least one
optionally further substituted by one or more substituents selected from the group consisting of deuterium, halogen, 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, and combinations thereof;
wherein any two adjacent substituents are optionally fused or joined to form a ring.
2. The compound of claim 1 , wherein the first, and second conjugated ring systems are each an aromatic ring system.
3. The compound of claim 1 , wherein the first, second and third conjugated ring systems are all the same.
4. The compound of claim 1 , wherein the first, second and third conjugated ring systems are all different from each other.
5. The compound of claim 1 , wherein among the first, second and third conjugated ring systems, two of them are the same, and the other one is different.
6. The compound of claim 1 ,
wherein the compound of Formula I is a compound of Formula II:
wherein R 1 , R 2 , and R 3 are each independently selected from the group consisting of deuterium, alkyl, cycloalkyl, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, and combinations thereof; and
wherein any two adjacent substituents are optionally fused or joined to form a 5-member hetero-aromatic ring.
7. The compound of claim 6 , wherein at least one of R 1 , R 2 , and R 3 is selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
8. The compound of claim 6 , wherein the compound is selected from the group consisting of:
9. The compound of claim 1 , wherein the compound of Formula I is a compound of Formula III:
10. The compound of claim 9 , wherein the first conjugated ring system is naphthalene, and the second conjugated ring system is the same as the third conjugated ring system.
11. The compound of claim 9 , wherein the first and second conjugated ring systems are the same as the third conjugated ring system.
12. The compound of claim 9 , wherein the compound is selected from the group consisting of:
13. The compound of claim 1 , wherein the compound is selected from the group consisting of:
14. 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 comprising a [n 1 .n 2 .n 3 ]propellane of Formula I:
wherein L 1 comprises a carbon chain having (n 1 -2) carbon atoms, L 2 comprises a carbon chain having (n 2 -2) carbon atoms, and L 3 comprises a carbon chain having (n 3 -2) carbon atoms;
wherein n 1 , n 2 , and n 3 are each independently an integer of 3 or 4;
wherein C 11 -L 1 -C 1n1 forms a first conjugated ring system, C 21 -L 2 -C 2n2 forms a second conjugated ring system, and C 31 -L 3 -C 3n3 forms a third conjugated ring system;
wherein C 31 -L 3 -C 3n3 is selected from the group consisting of:
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;
wherein R and R′ are optionally fused or joined to form a ring;
wherein the first, second and third conjugated ring systems are each optionally further substituted by one or more substituents selected from the group consisting of deuterium, halogen, 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, and combinations thereof;
wherein any two adjacent substituents are optionally fused or joined to form a ring; and
with the proviso that when the first, second and third conjugated ring systems are each a naphthalene as shown in the following structure:
at least one of the first, second and third conjugated ring systems is substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein any two adjacent substituents are optionally fused or joined to form a 5-member hetero-aromatic ring; and
with the proviso that Formula I comprises at least one
optionally further substituted by one or more substituents selected from the group consisting of deuterium, halogen, 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, and combinations thereof;
wherein any two adjacent substituents are optionally fused or joined to form a ring.
15. The OLED of claim 14 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.
16. The OLED of claim 14 , wherein the organic layer is a blocking layer and the compound of Formula I is a blocking material in the organic layer, or the organic layer is a transporting layer and the compound of Formula I is a transporting material in the organic layer.
17. The OLED of claim 14 , 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. A formulation comprising a compound comprising a [n 1 .n 2 .n 3 ]propellane of Formula I:
wherein L 1 comprises a carbon chain having (n 1 -2) carbon atoms, L 2 comprises a carbon chain having (n 2 -2) carbon atoms, and L 3 comprises a carbon chain having (n 3 -2) carbon atoms;
wherein n 1 , n 2 , and n 3 are each independently an integer of 3 or 4;
wherein C 11 -L 1 -C 1n1 forms a first conjugated ring system, C 21 -L 2 -C 2n2 forms a second conjugated ring system, and C 31 -L 3 -C 3n3 forms a third conjugated ring system;
wherein C 31 -L 3 -C 3n3 is selected from the group consisting of:
wherein X is selected from the group consisting of BR, NR, PR, O, S, Se, C═O, S═O, SO 2 , CRR′, SiRR′, and GeRR′;
wherein R and R′ are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;
wherein R and R′ are optionally fused or joined to form a ring;
wherein the first, second and third conjugated ring systems are each optionally further substituted by one or more substituents selected from the group consisting of deuterium, halogen, 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, and combinations thereof;
wherein any two adjacent substituents are optionally fused or joined to form a ring; and
with the proviso that when the first, second and third conjugated ring systems are each a naphthalene as shown in the following structure:
at least one of the first, second and third conjugated ring systems is substituted by one or more substituents selected from the group consisting of deuterium, alkyl, cycloalkyl, heteroalkyl, arylalkyl, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, wherein any two adjacent substituents are optionally fused or joined to form a 5-member hetero-aromatic ring; and
with the proviso that Formula I comprises at least one
optionally further substituted by one or more substituents selected from the group consisting of deuterium, halogen, 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, and combinations thereof;
wherein any two adjacent substituents are optionally fused or joined to form a ring.
19. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising the compound of claim 9 .