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US 9,312,499 B1Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorLichang Zeng
Life of this patent
Estimating the term…
Abstract
Compounds having a structure of Formula I, where G1 has the formula having the structure are described. In the structure of Formula I: Z1 to Z24 are each independently selected from group consisting of carbon and nitrogen; p is an integer from 1 to 10; adjacent carbazole groups G11, G12, and G13 are each bonded together either by a 9N-2C bond or a 9N-3C bond; G1 can include at least one 9N-2C intercarbazole bond and at least one 9N-3C intercarbazole bond; L and G2 are each independently selected from the group consisting of alkyl, aryl, or heteroaryl, which may be further substituted; m and n are both integers; and m+n ranges from 1 to the maximum number of possible substituents on L. Formulations and devices, such as an OLEDs, that include the compound of Formula I are also described.
Claims20
A compound having a structure of Formula I:
- Formula I;
- wherein G1 has the formula
- having the structure:
- wherein Z1 to Z24 are each independently selected from group consisting of carbon and nitrogen;
- wherein when any of Z1 to Z24 are nitrogen, there is no substitution on that nitrogen;
- wherein R1, R3, R5 and R6 each independently represent mono, di, tri, or tetra substitution, or no substitution;
- wherein R2 and R4 each independently represent mono, di, or tri substitution, or no substitution;
- wherein p is an integer from 1 to 10;
- wherein, when p is greater than 1, each G12 can be same or different;
- wherein adjacent carbazole groups G11 and G12 are each bonded together either by a 9N-2C bond or a 9N-3C bond;
- wherein G1 comprises at least one 9N-2C intercarbazole bond;
- wherein G13 is bonded to G12 by a 9N-3C intercarbazole bond;
- wherein R1 to R6 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 L and G2 are each independently selected from the group consisting of alkyl, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, benzothienobenzofuran, benzothienobenzothiophene, benzofluorenofuran, benzothienocarbazole, benzofuranocarbazole, indenofluorene, indenocarbazole, indenodibenzothiophene, indenodibenzofuran, indolocarbazole, aza-dibenzofuran, aza-dibenzothiophene, diaza-dibenzothiophene, aza-carbazole, aza-fluorene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine;
- wherein L and G2 are each independently optionally further substituted with one or more moieties selected from the group consisting of deuterium, alkyl, alkyloxyl, halogen, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine, and combinations thereof;
- wherein m is an integer 1 or larger representing the number of G1 substituents bonded to L, wherein, when m is greater than 1, each G1 can be the same or different;
- wherein n is an integer 0 or larger representing the number of G2 substituents bonded to L, wherein, when n is greater than 1, each G2 can be the same or different;
- and
- wherein m+n ranges from 1 to the maximum number of possible substituents on L.
16 more elements
A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and the cathode, comprising a compound having a structure of Formula I:
- Formula I;
- wherein G1 has the formula
- having the structure:
- wherein Z1 to Z24 are each independently selected from group consisting of carbon and nitrogen;
- wherein when any of Z1 to Z24 are nitrogen, there is no substitution on that nitrogen;
- wherein R1, R3, R5 and R6 each independently represent mono, di, tri, or tetra substitution, or no substitution;
- wherein R2 and R4 each independently represent mono, di, or tri substitution, or no substitution;
- wherein p is an integer from 1 to 10;
- wherein when p is greater than 1, each G12 can be same or different;
- wherein adjacent carbazole groups G11 and G12 are each bonded together either by a 9N-2C bond or a 9N-3C bond;
- wherein G1 comprises at least one 9N-2C intercarbazole bond;
- wherein G13 is bonded to G12 by a 9N-3C intercarbazole bond;
- wherein R1 to R6 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 L and G2 are each independently selected from the group consisting of alkyl, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, benzothienobenzofuran, benzothienobenzothiophene, benzofluorenofuran, benzothienocarbazole, benzofuranocarbazole, indenofluorene, indenocarbazole, indenodibenzothiophene, indenodibenzofuran, indolocarbazole, aza-dibenzofuran, aza-dibenzothiophene, diaza-dibenzothiophene, aza-carbazole, aza-fluorene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine;
- wherein L and G2 are each independently optionally further substituted with one or more moieties selected from the group consisting of deuterium, alkyl, alkyloxyl, halogen, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine, and combinations thereof;
- wherein m is an integer 1 or larger representing the number of G1 substituents bonded to L, wherein, when m is greater than 1, each G1 can be the same or different;
- wherein n is an integer 0 or larger representing the number of G2 substituents bonded to L, wherein, when n is greater than 1, each G2 can be the same or different;
- and
- wherein m+n ranges from 1 to the maximum number of possible substituents on L.
20 more elements
A formulation comprising a compound having a structure of Formula I:
- formula I;
- wherein G1 has the formula
- having the structure:
- wherein Z1 to Z24 are each independently selected from group consisting of carbon and nitrogen;
- wherein when any of Z1 to Z24 are nitrogen, there is no substitution on that nitrogen;
- wherein R1, R3, R5 and R6 each independently represent mono, di, tri, or tetra substitution, or no substitution;
- wherein R2 and R4 each independently represent mono, di, or tri substitution, or no substitution;
- wherein p is an integer from 1 to 10;
- wherein when p is greater than 1, each G12 can be same or different;
- wherein adjacent carbazole groups G11 and G12 are each bonded together either by a 9N-2C bond or a 9N-3C bond;
- wherein G1 and comprises at least one 9N-2C intercarbazole bond;
- wherein G13 is bonded to G12 by a 9N-3C intercarbazole bond;
- wherein R1 to R6 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 L and G2 are each independently selected from the group consisting of alkyl, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, benzothienobenzofuran, benzothienobenzothiophene, benzofluorenofuran, benzothienocarbazole, benzofuranocarbazole, indenofluorene, indenocarbazole, indenodibenzothiophene, indenodibenzofuran, indolocarbazole, aza-dibenzofuran, aza-dibenzothiophene, diaza-dibenzothiophene, aza-carbazole, aza-fluorene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine;
- wherein L and G2 are each independently optionally further substituted with one or more moieties selected from the group consisting of deuterium, alkyl, alkyloxyl, halogen, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine, and combinations thereof;
- wherein m is an integer 1 or larger representing the number of G1 substituents bonded to L, wherein, when m is greater than 1, each G1 can be the same or different;
- wherein n is an integer 0 or larger representing the number of G2 substituents bonded to L, wherein, when n is greater than 1, each G2 can be the same or different;
- and
- wherein m+n ranges from 1 to the maximum number of possible substituents on L.
16 more elements
Dependencies are inferred from the claim text.