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US 2019/0097141 A1Published application
Organic molecules for use in optoelectronic devices
AssigneeCynora GmbH
InventorDaniel Zink
Life of this patent
Estimating the term…
Abstract
Organic molecules are provided for use in organic optoelectronic devices. The organic molecules are purely organic molecules, i.e., they do not contain any metal ions. The organic molecules exhibit emission maxima in the blue, sky-blue or green spectral range. The organic molecules exhibit emission maxima between 420 nm and 520 nm, between 440 nm and 495 nm, or between 450 nm and 470 nm. The photoluminescence quantum yields of the organic molecules are 20% or more. The molecules exhibit thermally activated delayed fluorescence (TADF). Use of the molecules in an optoelectronic device, e.g., an organic light-emitting diode (OLED) leads to higher efficiencies of the device. Corresponding OLEDs have higher stabilities than OLEDs with known emitter materials and comparable color.
Claims17
An organic molecule, comprising
- one first chemical moiety comprising a structure of formula I,
- and
- two second chemical moieties, each independently from another comprising a structure of formula II,
- wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond;
- wherein
- T is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, RA and R1;
- V is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, RA and R1;
- W is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, RA and R1;
- X is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, RA and R1;
- Y is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, RA and R1;
- RA is consisting of a structure of formula A1,
- wherein $ represents the binding site of the single bond connecting RA to the first chemical moiety as shown in formula I;
- AI, AII, AIII, AIV and AV are each selected from the group consisting of CF3 and RI;
- RT is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R2;
- RV is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R2;
- RW is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R2;
- RX is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R2;
- RY is selected from the group consisting of the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties, CN and R2;
- # represents the binding site of a single bond linking the second chemical moieties to the first chemical moiety;
- Z is at each occurrence independently from another selected from the group consisting of a direct bond, CR3R4, C═CR3R4, C═O, C═NR3, NR3, O, SiR3R4, S, S(O) and S(O)2;
- R1 is at each occurrence independently from another selected from the group consisting of:
- hydrogen, deuterium,
- C1-C5-alkyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- C2-C8-alkenyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- C2-C8-alkynyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- and
- C6-C18-aryl,
- which is optionally substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, OPh, C1-C5-alkyl, C2-C5-alkenyl and C2-C5-alkynyl.
- R2 is at each occurrence independently from another selected from the group consisting of:
- hydrogen, deuterium,
- C1-C5-alkyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- C2-C8-alkenyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- C2-C8-alkynyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- and
- C6-C18-aryl,
- which is optionally substituted with one or more substituents selected from the group consisting of hydrogen, deuterium, OPh, C1-C5-alkyl, C2-C5-alkenyl and C2-C5-alkynyl.
- RI is at each occurrence independently from another selected from the group consisting of
- hydrogen,
- deuterium,
- C1-C5-alkyl,
- wherein one or more hydrogen atoms are optionally substituted by deuterium;
- and
- C6-C18-aryl,
- which is optionally substituted with one or more substituents R6.
- Ra, R3 and R4 is at each occurrence independently from another selected from the group consisting of:
- hydrogen, deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, OSO2R5, CF3, CN, F, Br, I,
- C1-C40-alkyl,
- which is optionally substituted with one or more substituents R5 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
- C1-C40-alkoxy,
- which is optionally substituted with one or more substituents R5 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
- C1-C40-thioalkoxy,
- which is optionally substituted with one or more substituents R5 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
- C2-C40-alkenyl,
- which is optionally substituted with one or more substituents R5 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
- C2-C40-alkynyl,
- which is optionally substituted with one or more substituents R5 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
- C6-C60-aryl,
- which is optionally substituted with one or more substituents R5;
- and
- C3-C57-heteroaryl,
- which is optionally substituted with one or more substituents R5;
- R5 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, OSO2R6, CF3, CN, F, Br, I,
- C1-C40-alkyl,
- which is optionally substituted with one or more substituents R6 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
- C1-C40-alkoxy,
- which is optionally substituted with one or more substituents R6 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
- C1-C40-thioalkoxy,
- which is optionally substituted with one or more substituents R6 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
- C2-C40-alkenyl,
- which is optionally substituted with one or more substituents R6 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
- C2-C40-alkynyl,
- which is optionally substituted with one or more substituents R6 and
- wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
- C6-C60-aryl,
- which is optionally substituted with one or more substituents R6;
- and
- C3-C57-heteroaryl,
- which is optionally substituted with one or more substituents R6;
- R6 is at each occurrence independently from another selected from the group consisting of:
- hydrogen, deuterium, OPh, CF3, CN, F,
- C1-C5-alkyl,
- wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
- C1-C5-alkoxy,
- wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
- C1-C5-thioalkoxy,
- wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
- C2-C5-alkenyl,
- wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
- C2-C5-alkynyl,
- wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
- C6-C18-aryl,
- which is optionally substituted with one or more C1-C5-alkyl substituents;
- C3-C17-heteroaryl,
- which is optionally substituted with one or more C1-C5-alkyl substituents;
- N(C6-C18-aryl)2,
- N(C3-C17-heteroaryl)2, and
- N(C3-C17-heteroaryl)(C6-C18-aryl);
- wherein the substituents Ra, R3, R4 or R5 optionally form, independently from each other, a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents Ra, R3, R4 or R5;
- wherein
- exactly one substituent selected from the group consisting of T, V, W, X and Y is RA;
- exactly one substituent selected from the group consisting of RT, RV, RW, RX and RY is CN;
- exactly one substituent selected from the group consisting of T, V, W, X and Y represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties;
- exactly one substituent selected from the group consisting of RT, RV, RW, RX and RY represents the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties;
- and
- exactly two substituents selected from the group consisting of AI, AII, AIII, AIV and AV are CF3.
117 more elements
Dependencies are inferred from the claim text.