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US 12,378,197 B2Granted
Organic electroluminescent materials and devices
AssigneeUniversal Display Corporation
InventorsHsiao-Fan Chen, Peter Wolohan, Nicholas J. Thompson
Life of this patent
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Abstract
A compound having a structure of Formula I, is provided. In Formula I, Z1 to Z16 are each CR or N; three consecutive ones of Z1 to Z16 within the same ring cannot be N; each R is independently a hydrogen or a substituent selected from a variety of substituents; at least one R includes and electron donor substituent; at least one R includes an electron acceptor substituent; and any two Rs on the same ring can be joined or fused together to form a ring. Organic light emitting devices, consumer products, formulations, and chemical structures containing the compounds are also disclosed.
Claims20
A compound having exactly one structure of Formula I:
- wherein Z1 to Z16 are each CR or N;
- wherein three consecutive ones of Z1 to Z16 within the same ring cannot be N;
- wherein each R is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one R comprises a donor substituent selected from the group consisting of carbazole, indolocarbazole, indoloindole, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, diphenylamino,
- phenoxazine, phenothiazine, dibenzoazasiline, pyrrolidine, piperidine, phenoxide, and methoxide;
- wherein at least one R comprises an acceptor substituent selected from the group consisting of a halogen, a nitrile group, a 5-membered aromatic ring containing at least two heteroatoms, and a 6-membered heteroaromatic ring;
- wherein the at least one R comprising a donor substituent and the at least one R comprising an acceptor substituent are different;
- wherein at least one of the following is true:
- (i) wherein at least one R comprises a donor substituent selected from the group consisting of indolocarbazole, indoloindole, phenoxazine, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, dibenzoazasiline, and pyrrolidine, or (ii) the compound has exactly one donor substituent and exactly one acceptor substituent, and the acceptor substituent comprises heteroaryl;
- and
- wherein any two Rs on the same 6-membered ring can be joined or fused together to form a ring, and Rs from different 6-membered rings cannot be joined, with the proviso that if the acceptor is selected from the group consisting of aza-carbazole, aza-dibenzofuran and aza-dibenzothiophene, then the donor is not carbazole.
8 more elements
A compound selected from the group consisting of the following compounds:
- Compound Z
- Structure of Compound Z
- Ar1, Ar2, Ar3, Ar4
- Z
- Compound 1 to Compound 540,000 having the structure
- wherein Ar1 = Di, Ar2 = Aj, Ar3 = Ak, and Ar4 = Al, wherein i is an integer from 1 to 20, j is an integer from 1 to 30, k is an integer from 1 to 30, and l is an integer from 1 to 30,
- wherein Z = i + 20(j − 1) + 600 (k − 1) + 18,000 (l − 1),
- Compound 540,001 to Compound 1436,000 having the structure
- wherein Ar1 = Ai, Ar2 = Dj, Ar3 = Dk, and Ar4 = Dl, wherein i is an integer from 1 to 14, j is an integer from 1 to 40, k is an integer from 1 to 40, and l is an integer from 1 to 40,
- wherein Z = i + 14(j − 1) + 560 (k − 1) + 22,400 (l − 1) + 540,000,
- Compound 1,436,001 to Compound 1,468,000 having the structure
- wherein Ar1 = Ai, Ar2 = Dj, Ar3 = Dk, and Ar4 = Dl, wherein i is an integer from 29 to 30, j is an integer from 1 to 40, k is an integer from 1 to 20, and l is an integer from 1 to 20,
- wherein Z = (i − 28) + 2(j − 1) + 80(k − 1) +1,600 (l − 1) + 1,4360,000,
- Compound 1,468,001 to Compound 1,484,000 having the structure
- wherein Ar1 = Ai, Ar2 = Dj, Ar3 = Dk, and Ar4 = Dl, wherein i is an integer from 29 to 30, j is an integer from 21 to 40, k is an integer from 1 to 20, and l is an integer from 21 to 40,
- wherein Z = (i − 28) + 2(j − 21) + 40(k − 1) + 800 (l −21) + 1,468,000,
- Compound 1,484,001 to Compound 2,204,000 having the structure
- wherein Ar1 = Di, Ar2 = Aj, Ar3 = Ak, and Ar4 = Al, wherein i is an integer from 1 to 20, j is an integer from 1 to 40, k is an integer from 1 to 30, and i is an integer from 1 to 30,
- wherein Z = i + 20(j − 1) + 800 (k − 1) + 24,000 (l − 1) + 1,484,000,
- Compound 2,204,001 to Compound 2,924,000 having the structure
- wherein Ar1 = Di, Ar2 = Aj, Ar3 = Dk, and Ar4 = Al, wherein i is an integer from 1 to 20, j is an integer from 1 to 30, k is an integer from 1 to 40, and l is an integer from 1 to 30,
- wherein Z = i + 20(j − 1) + 600 (k − 1) + 24,000 (l − 1) + 2,204,000,
- Compound 2,924,001 to Compound 2,946,400 having the structure
- wherein Ar1 = Di, Ar2 = Aj, and Ar3 = Dk, wherein i is an integer from 1 to 40, j is an integer from 1 to 14, and k is an integer from 1 to 40,
- wherein Z = i + 14(j − 1) + 560 (k − 1) + 2,924,000,
- Compound 2,946,401 to Compound 2,948,000 having the structure
- wherein Ar1 = Di, Ar2 = Aj and Ar3 = Dk, wherein i is an integer from 1 to 40, j is an integer from 29 to 30, and k is an integer from 1 to 20,
- wherein Z = i + 40(j − 29) + 80 (k − 1) + 2,946,400,
- Compound 2,948,001 to Compound 2,948,800 having the structure
- wherein Ar1 = Di, Ar2 = Aj, and Ar3 = Dk, wherein i is an integer from 21 to 40, j is an integer from 29 to 30, and k is an integer from 21 to 40,
- wherein Z = (i − 20) + 2(j − 29) + 40(k − 21) + 2,948,000,
- Compound 2,948,801 to Compound 2,966,800 having the structure
- wherein Ar1 = Ai, Ar2 = Dj, and Ar3 = Ak, wherein i is an integer from 1 to 30, j is an integer from 1 to 20, and k is an integer from 1 to 30,
- wherein Z = i + 30(j − 1) + 600 (k − 1) + 2,948,800,
- Compound 2,966,801 to Compound 3,014,800 having the structure
- wherein Ar1 = Di, Ar2 = Dj, and Ar3 = Ak, wherein i is an integer from 1 to 40, j is an integer from 1 to 40, and k is an integer from 1 to 30,
- wherein Z = i + 40(j − 1) + 1,600(k − 1) + 2,966,800,
- Compound 3,014,801 to Compound 3,062,800 having the structure
- wherein Ar1 = Ai, Ar2 = Dj, and Ar3 = Dk, wherein i is an integer from 1 to 30, j is an integer from 1 to 40, and k is an integer from 1 to 40,
- wherein Z = i + 30(j − 1) + 1,200(k − 1) + 3,014,800,
- Compound 3,062,801 to Compound 3,063,400 having the structure
- wherein Ar1 = Di and Ar2 = Aj, wherein i is an integer from 1 to 20 and j is an integer from 1 to 30,
- wherein Z = i + 20(j − l) + 3,062,800,
- Compound 3,063,401 to Compound 3,064,600 having the structure
- wherein Ar1 = Di and Ar2 = Aj, wherein i is an integer from 1 to 40 and j is an integer from 1 to 30,
- wherein Z = i + 40(j − 1) + 3,063,400;
- with the proviso that donor D2 cannot be present in the same compound as any acceptor selected from the group consisting of A7-A10, A13, A14, A24-A26, and A28-A29;
- with the proviso that at least one of the following moieties is present:
- D2-D5, D7, D10-D20, D23-D25, D27, D30, D32-D40, A2-10, A12-15, and A18-A30;
- with the proviso that if the donor substituent is DI or D11, then the acceptor substituent is not A1, A11, or A17;
- wherein D1 to D40 have the following structures:
- and
- wherein A1 to A30 have the following structures:
50 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an emissive layer, disposed between the anode and cathode, wherein the emissive layer comprises a compound that is an emitter having a structure of Formula I:
- wherein Z1 to Z16 are each CR or N;
- wherein three consecutive ones of Z1 to Z16 within the same ring cannot be N;
- wherein each R is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one R comprises a donor substituent selected from the group consisting of carbazole, indolocarbazole, indoloindole, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, diphenylamino, phenoxazine, phenothiazine, dibenzoazasiline, pyrrolidine, piperidine, phenoxide, and methoxide;
- wherein at least one R comprises an acceptor substituent selected from the group consisting of a halogen, a nitrile group, a 5-membered aromatic ring containing at least two heteroatoms, and a 6-membered heteroaromatic ring;
- wherein the at least one R comprising a donor substituent and the at least one R comprising an acceptor substituent are different;
- wherein at least one of the following is true:
- (i) wherein at least one R comprises a donor substituent selected from the group consisting of indolocarbazole, indoloindole, phenothiazine, diphenylamino, phenoxazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, dibenzoazasiline, pyrrolidine, piperidine, and phenoxide, or (ii) at least one acceptor substituent comprises aryl or heteroaryl, and each of Z1 to Z16 is CR;
- if the donor substituents is diphenylamino and the acceptor substituent is nitrile, then two Rs on the same 6-membered ring cannot be joined to form a 5-membered ring;
- and
- wherein any two Rs on the same 6-membered ring can be joined or fused together to form a ring, and Rs from different 6-membered rings cannot be joined, with the proviso that if the acceptor is selected from the group consisting of aza-carbazole, aza-dibenzofuran and aza-dibenzothiophene, then the donor is not carbazole.
12 more elements
An organic light emitting device (OLED) comprising:
- an anode;
- a cathode;
- and
- an organic layer, disposed between the anode and cathode, comprising a compound having a structure of Formula I:
- wherein Z1 to Z16 are each CR or N;
- wherein three consecutive ones of Z1 to Z16 within the same ring cannot be N;
- wherein each R is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- wherein at least one R comprises a donor substituent selected from the group consisting of carbazole, indolocarbazole, indoloindole, phenothiazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, diphenylamino, phenoxazine, phenothiazine, dibenzoazasiline, pyrrolidine, piperidine, phenoxide, and methoxide;
- wherein at least one R comprises an acceptor substituent selected from the group consisting of a halogen, a nitrile group, a 5-membered aromatic ring containing at least two heteroatoms, and a 6-membered heteroaromatic ring;
- wherein the at least one R comprising a donor substituent and the at least one R comprising an acceptor substituent are different;
- wherein at least one of the following is true:
- (i) each of Z1 to Z16 is CR, (ii) wherein at least one R comprises a donor substituent selected from the group consisting of indolocarbazole, indoloindole, phenothiazine, diphenylamino, phenoxazine, 5H-benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, dibenzoazasiline, pyrrolidine, piperidine, and phenoxide, (iii) at least one donor substituent comprises aryl or heteroaryl, or (iv) at least one acceptor substituent comprises aryl or heteroaryl;
- and
- wherein any two Rs on the same 6-membered ring can be joined or fused together to form a ring, and Rs from different 6-membered rings cannot be joined, with the proviso that if the acceptor is selected from the group consisting of aza-carbazole, aza-dibenzofuran and aza-dibenzothiophene, then the donor is not carbazole, wherein the OLED emits a luminescent radiation at room temperature when a voltage is applied across the first organic light emitting device;
- wherein the luminescent radiation comprises a delayed fluorescent process.
12 more elements
Dependencies are inferred from the claim text.