Patent ID: 11873293
Assignee: SAMSUNG ELECTRONICS CO., LTD.
Field: Organic fine chemistry (Chemistry)
Classification: CPC C  H  Y | IPC C  H

Claim 0:
1. An optoelectronic device comprising:
a substrate;
a first electrode;
a second electrode, wherein the first electrode or the second electrode is applied to the substrate; and
at least one light-emitting layer disposed between the first electrode and the second electrode and which comprises a compound of formula I:, wherein
X1 and X2 are at each occurrence independently selected from the group consisting of CR21 and N;
X3 and X4 are at each occurrence independently selected from the group consisting of CR22 and N;
X5 and X6 are at each occurrence independently selected from the group consisting of CR23 and N;
R11 is at each occurrence independently 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;
C6-C18-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R6;
R12 is at each occurrence independently 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;
C6-C18-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R6;
R13 is at each occurrence independently 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;
C6-C18-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R6;
R21 is at each occurrence independently 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;
C6-C18-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R6;
R22 is at each occurrence independently 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;
C6-C18-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R6;
R23 is at each occurrence independently 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;
C6-C18-aryl,
which is optionally substituted with one or more substituents R6; and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R6;
RII, RIII and RIV are independently 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 R6;
Ra is at each occurrence independently 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, O═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 selected from the group consisting of: hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, OSO2R6, CF3, CN, F, Br,
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, O═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 selected from the group consisting of: hydrogen, deuterium, OPh, CF3, CN, F,
C1-C5 alkyl,
wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
C1-C5-alkoxy,
wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF2, or F;
C1-C5-thioalkoxy,
wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
C2-C5 alkenyl,
wherein one or more hydrogen atoms are optionally, independently substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl,
wherein one or more hydrogen atoms are optionally, independently 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, optionally, the substituents Ra or R5 independently form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents Ra or R5;
wherein
at least one variable selected from the group consisting of X1, X2 is N;
at least one variable selected from the group consisting of X3, X4 is N; and
at least one variable selected from the group consisting of X5, X6 is N, and
wherein the compound of formula I has a ΔEST value of less than 5000 cm−1, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1).