Organic electroluminescent materials and devices
A composition comprising a first compound and a second compound is described. The composition can be a mixture of a first compound having a structure according to Formula I, and a second compound having a structure according to Formula II, The composition can also be a mixture of a first compound having a structure according to Formula III, and a second compound having a structure according to Formula IV, Devices, such as OLEDs, that include the compositions for Formulas I & II or Formulas III & IV, as well as, methods of making the same are also described.
1. A composition of materials comprising a first compound, wherein the first compound has a formula:
wherein G 2 , G 3 , and, when present, G 4 are each optionally further substituted with one or more unfused substituents selected from the group consisting of deuterium, alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, halogen, nitro, nitrile, silyl, phenyl, biphenyl, terphenyl, pyridine, and combinations thereof; and
wherein
(A) when m=0, L 1 is biphenyl, L 2 is a direct bond, L 3 is a direct bond,
G 1 is selected from the group consisting of dibenzoselenophene and fluorene, and
G 2 and G 3 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof; and
(B) when m is 1 to 7, G 1 is selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and fluorene, and each G 4 is independently selected from the group consisting of phenyl, and biphenyl, and at least one G 4 is biphenyl,
wherein L 1 , L 2 and L 3 are each independently selected from the group consisting of direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof, and
G 2 and G 3 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof.
2. The composition of claim 1 , wherein m is 0.
3. The composition of claim 1 , wherein each G 4 is independently selected from the group consisting of:
and
the first G 4 is selected from the group consisting of
and
4. The composition of claim 1 , wherein G′ has the structure selected from the group consisting of:
wherein, when m=0, X is Se, and, wherein m is 1 to 7, X is selected from a group consisting of O, S and Se;
wherein R B1 and R B2 are independently selected from a group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxyl, aryl, heteroaryl, halogen, and combinations thereof; and
wherein R B1 and R B2 are optionally joined to form a ring.
5. The composition of claim 1 , wherein m is equal to or greater than 1 and L 1 is selected from the group consisting of:
6. The composition of claim 1 , wherein, consistent with limitation (A) or (B), G 2 and G 3 are independently selected from the group consisting of:
wherein R B1 and R B2 are independently selected from a group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxyl, aryl, heteraryl, halogen, and combinations thereof; and
wherein R B1 and R B2 are optionally joined to form a ring.
7. The composition of claim 1 , wherein at least one of G 2 , G 3 , and, when present, G 4 is substituted with at least one fluorine atom.
8. The composition of claim 1 , wherein, when m is 1, G 4 -G 1 has a structure selected from the group consisting of:
wherein X is selected from the group consisting of O, S, Se, and CR B1 R B2 , and
wherein R B1 and R B2 are independently selected from a group consisting of hydrogen, deuterium, alkyl, cycloalkyl, alkoxyl, aryl, heteraryl, halogen, and combinations thereof; and
wherein R B1 and R B2 are optionally joined to form a ring.
9. The composition of claim 1 , wherein the first compound has a formula:
wherein L 1 is biphenyl.
10. The composition of claim 1 , wherein the composition comprises a second compound;
wherein the second compound has the formula II:
wherein Ar 1 is selected from the group consisting of triphenylene, and aza-triphenylene;
wherein Ar 2 is selected from the group consisting of a direct bond, phenyl, biphenyl, terphenyl, naphthalene, pyridine, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, and combinations thereof;
wherein Ar 3 is selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, pyridine, dibenzofuran, dibenzothiophene, dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, carbazole, aza-carbazole, and combinations thereof; and
wherein Ar 1 , Ar 2 and Ar a are each, independently, optionally further substituted with one or more substitutions selected from the group consisting of deuterium, halogen, alkyl, aryl, heteroaryl, and combinations thereof.
11. The composition of claim 10 , wherein the second compound is selected from the group consisting of
wherein X is selected from the group consisting of O, S and Se;
wherein R 1 and R 4 each independently represents mono, di, or tri, substitution, or no substitution;
wherein R 2 , R 3 , R 5 , and R 6 each independently represents mono, di, tri, or tetra substitution, or no substitution; and
wherein R 1 to R 6 are each independently selected from the group consisting of hydrogen, deuterium, benzene, biphenyl, terphenyl, naphthalene, fluorene, triphenylene, phenanthrene, dibenzofuran, dibenzothiophene, carbazole and combinations thereof.
12. The composition of claim 10 , wherein the second compound is selected from the group consisting of
13. A composition comprising a mixture of a first compound and a second compound selected from the group consisting of:
14. The composition of claim 1 , wherein the composition comprises a second compound; wherein the second compound is a phosphorescent emissive Ir complex having at least one substituent selected from the group consisting of alkyl, cycloalkyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.
15. The composition of claim 1 , wherein the first compound is selected from the group consisting of:
16. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a composition of materials comprising a first compound, wherein the first compound has a formula:
wherein G 2 , G 3 , and, when present, G 4 are each optionally further substituted with one or more unfused substituents selected from the group consisting of deuterium, alkyl, alkoxyl, cycloalkyl, cycloalkoxyl, halogen, nitro, nitrile, silyl, phenyl, biphenyl, terphenyl, pyridine, and combinations thereof; and
wherein
(A) when m=0, L 1 is biphenyl, L 2 is a direct bond, L 3 is a direct bond,
G 1 is selected from the group consisting of dibenzoselenophene and fluorene, and
G 2 and G 3 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof; and
(B) when m is 1 to 7, G 1 is selected from the group consisting of dibenzofuran, dibenzothiophene, dibenzoselenophene, and fluorene, and each G 4 is independently selected from the group consisting of phenyl, and biphenyl, and at least one G 4 is biphenyl,
wherein L 1 , L 2 and L 3 are each independently selected from the group consisting of direct bond, phenyl, biphenyl, terphenyl, pyridine, pyrimidine, and combinations thereof, and
G 2 and G 3 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, fluorene, naphthalene, phenanthrene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phenanthroline, aza-fluorene, and combinations thereof.
17. The first device of claim 16 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the phosphorescent emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate 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′, R″, 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 e , 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; and
wherein any two adjacent substitutents of R a , R b , R e , and R d are optionally fused or joined to form a ring or form a multidentate ligand.
18. The first device of claim 16 , wherein the organic layer is a blocking layer and the composition is a blocking material in the organic layer.
19. The first device of claim 16 , wherein the organic layer is an electron transporting layer and the composition is an electron transporting material in the organic layer.
20. The composition of claim 1 , wherein wherein m is equal to or greater than 1.