MATERIALS WITH AZA-DIBENZOTHIOPHENE OR AZA-DIBENZOFURAN CORE FOR PHOLED
First Claim
Patent Images
1. A process for making an aza-dibenzothiophene compound or an aza-dibenzofuran compound, comprising:
- treating an acetic acid solution of an amino-arylthio pyridine intermediate having the formula wherein one of X1 and X2 is nitrogen and the other of X1 and X2 is carbon and wherein Y is S or O, with tBuONO to produce an aza complex having the formula wherein R1 and R2 may represent mono, di, tri, or tetra substitutions;
wherein R1 is selected from the group consisting of hydrogen, alkyl, aryl, heteroaryl and halide; and
wherein R2 is selected from the group consisting of hydrogen, alkyl, aryl and halide.
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Abstract
A new class of compounds containing aza-dibenzothiophene or aza-dibenzofuran are provided. The compounds may be used in organic light emitting devices giving improved stability, improved efficiency, long lifetime and low operational voltage. In particular, the compounds may be used as the host material of an emissive layer having a host and an emissive dopant, or as a material in an enhancement layer.
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Citations
20 Claims
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1. A process for making an aza-dibenzothiophene compound or an aza-dibenzofuran compound, comprising:
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treating an acetic acid solution of an amino-arylthio pyridine intermediate having the formula wherein one of X1 and X2 is nitrogen and the other of X1 and X2 is carbon and wherein Y is S or O, with tBuONO to produce an aza complex having the formula wherein R1 and R2 may represent mono, di, tri, or tetra substitutions; wherein R1 is selected from the group consisting of hydrogen, alkyl, aryl, heteroaryl and halide; and wherein R2 is selected from the group consisting of hydrogen, alkyl, aryl and halide. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
is greater than 50%.
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11. A compound having the formula:
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wherein X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from the group consisting of a carbon atom and a nitrogen atom; wherein at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is a nitrogen atom; wherein Y is S or O; wherein R1 and R2 may represent mono, di, tri, or tetra substitutions; wherein R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and wherein at least one of R1 and R2 is selected from the group consisting of; wherein R′
1, R′
2, R′
3, and R′
4 may represent mono, di, tri, tetra or penta substitutions; andwherein R′
1, R′
2, R′
3, and R′
4 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.- View Dependent Claims (12, 13, 14, 15)
wherein X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from the group consisting of a carbon atom and a nitrogen atom; wherein at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is a nitrogen atom; wherein Y is S or O; wherein R1 and R2 may represent mono, di, tri, or tetra substitutions; wherein R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and wherein at least one of R1 and R2 is selected from the group consisting of; wherein R′
1, R′
2, R′
3, and R′
4 may represent mono, di, tri, tetra or penta substitutions; andwherein R′
1, R′
2, R′
3, and R′
4 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.
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13. The compound of claim 12, wherein m and n are 0, 1, 2, 3, or 4;
- and wherein m+n is equal to or greater than 2 and m+n is equal to or less than 6.
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14. The compound of claim 11, wherein the compound is selected from the group consisting of:
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15. The compound of claim 11, wherein the compound is selected from the group consisting of:
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16. A first device comprising an organic light emitting device, further comprising:
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an anode; a cathode; an organic layer disposed between the anode and the cathode, the organic layer further comprising a compound having the formula; wherein X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from the group consisting of a carbon atom and a nitrogen atom; wherein at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is a nitrogen atom; wherein Y is S or O; wherein R1 and R2 may represent mono, di, tri, or tetra substitutions; wherein R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and wherein at least one of R1 and R2 is selected from the group consisting of; wherein R′
1, R′
2, R′
3, and R′
4 may represent mono, di, tri, tetra or penta substitutions; andwherein R′
1, R′
2, R′
3, and R′
4 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.- View Dependent Claims (18, 19, 20)
wherein X1, X2, X3, X4, X5, X6, X7, and X8 are independently selected from the group consisting of a carbon atom and a nitrogen atom; wherein at least one of X1, X2, X3, X4, X5, X6, X7, and X8 is a nitrogen atom; wherein Y is S or O; wherein R1 and R2 may represent mono, di, tri, or tetra substitutions; wherein R1 and R2 are independently selected from the group consisting of hydrogen, alkyl, aryl and halide; and wherein at least one of R1 and R2 is selected from the group consisting of; wherein R′
1, R′
2, R′
3, and R′
4 may represent mono, di, tri, tetra or penta substitutions; andwherein R′
1, R′
2, R′
3, and R′
4 are independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl and heteroaryl.
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19. The device of claim 16, wherein the organic layer is an emissive layer and the compound having the formula
is a host. -
20. The device of claim 16, wherein the organic layer further comprises an emissive dopant and the emissive dopant has the formula:
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wherein R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, and aryl.
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17. The device of claim 17, wherein the first device is a consume product.
Specification