Organic electroluminescent materials and devices
A novel compound containing terphenylene connected to dibenzothiophene, dibenzofuran or dibenzoselenophene that can be used as hosts in phosphorescent organic light-emitting device is disclosed.
1. A compound having a structure according to a formula (I)
wherein A is selected from a group consisting of triphenylene, phenanthrene, anthracene, biphenyl, terphenyl, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, fluorene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, triazine, or combinations thereof;
wherein L is selected from a group consisting of a direct bond, benzene, biphenyl and terphenyl, pyridine, or combinations thereof, and wherein L is optionally further substituted with alkyl, halogen, hydrogen, deuterium, nitrite or aryl;
wherein B is selected from a group consisting of dibenzothiophene, dibenzofuran and dibenzoselenophene; and
wherein A and B are independently optionally further substituted with one or more substituents selected from the group consisting of 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, and for each of A and B, two adjacent substituents are optionally joined to form a ring.
2. The compound of claim 1 , wherein the compound is of formula (II) or (III)
wherein X is selected from a group consisting of O, S and Se.
3. The compound of claim 1 , wherein A is selected from the group consisting of
wherein X is S, O or Se; and
R 1 and R 2 are, independently, linear or branched alkyl with 1 to 12 carbon atoms, and R 1 and R 2 are optionally jointed to form a ring.
4. The compound of claim 1 , wherein B is selected from the group consisting of
5. The compound of claim 1 , wherein L is selected from the group consisting of a direct bond,
6. The compound of claim 1 , wherein the compound is selected from the group consisting of
7. A first device comprising a first phosphorescent organic light-emitting device, the phosphorescent organic light-emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a formula (I)
wherein A is selected from a group consisting of triphenylene, phenanthrene, anthracene, biphenyl, terphenyl, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, fluorene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, triazine, or combinations thereof;
wherein L is selected from a group consisting of a direct bond, benzene, biphenyl and terphenyl, pyridine, or combinations thereof, and wherein L is optionally further substituted with alkyl, halogen, hydrogen, deuterium, nitrile or aryl;
wherein B is selected from a group consisting of dibenzothiophene, dibenzofuran and dibenzoselenophene; and
wherein A and B are independently optionally further substituted with one or more substituents selected from the group consisting of 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, and for each of A and B, two adjacent substituents are optionally joined to form a fused ring.
8. The first device of claim 7 , wherein the compound is of formula (II)
wherein X is selected from a group consisting of O, S and Se.
9. The first device of claim 7 , wherein A is selected from the group consisting of
wherein X is S, O or Se; and
R 1 and R 2 are, independently, linear or branched alkyl with 1 to 12 carbon atoms, and R 1 and R 2 are optionally jointed to form a ring.
10. The first device of claim 7 , wherein B is selected from the group consisting of
11. The first device of claim 7 , wherein L is selected from the group consisting of a direct bond,
12. The first device of claim 7 , wherein the compound is selected from the group consisting of
13. The first device of claim 7 , wherein the organic layer is an emissive layer and the compound of the formula (I) is a host.
14. The first device of claim 7 , wherein the organic layer further comprising a phosphorescent emissive dopant.
15. The first device of claim 14 , wherein the phosphorescent emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:
wherein R a , R b , R c , and R d may represent mono, di, tri, or tetra substitution, or no substitution;
wherein R a , R b , R c , and R d are 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; and
wherein two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a fused ring or form a multidentate ligand.
16. The first device of claim 7 , wherein the organic layer is a blocking layer and the compound of the formula (I) is a blocking material in the organic layer.
17. The first device of claim 7 , wherein the organic layer is an electron transporting layer and the compound of the formula (I) is an electron transporting material in the organic layer.
18. The first device of claim 7 , wherein the first device is a consumer product.
19. The first device of claim 7 , wherein the first device is an organic light-emitting device.
20. The first device of claim 7 , wherein the first device comprises a lighting panel.
21. A formulation comprising the compound having a structure according to a formula (I)
wherein A is selected from a group consisting of triphenylene, phenanthrene, anthracene, biphenyl, terphenyl, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, fluorene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, triazine, or combinations thereof;
wherein L is selected from a group consisting of a direct bond, benzene, biphenyl and terphenyl, pyridine, or combinations thereof, and wherein L is optionally further substituted with alkyl, halogen, hydrogen, deuterium, nitrile or aryl;
wherein B is selected from a group consisting of dibenzothiophene, dibenzofuran and dibenzoselenophene; and
wherein A and B are independently optionally further substituted with one or more substituents selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and for each of A and B, two adjacent substituents are optionally joined to form a fused ring.