Organic molecules for optoelectronic devices

Abstract

The invention relates to organic molecules, in particular, for use in optoelectronic devices. According to the invention, the organic molecule has a first chemical moiety and a second chemical moiety, the first chemical moiety having a structure of Formula I-a or Formula I-b: the second chemical moiety having a structure of Formula II: wherein the first chemical moiety is linked to the second chemical moiety via a single bond; and wherein exactly one substituent selected from the group consisting of T, W, X, and Y is R X , and exactly one substituent selected from the group consisting of T, V and W represents the binding site of the single bond connecting the first chemical moiety to the second chemical moiety; and wherein, if T is R X and V is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, then W is hydrogen.

Description

Technical Field

[0001] The invention relates to organic molecules and the use of organic molecules in organic light emitting diodes (OLEDs) and in other optoelectronic devices. Background Art

[0002] The use of organic molecules in optoelectronic devices is being actively developed. Summary of the Invention

[0003] The object of the present invention is to provide organic molecules suitable for use in optoelectronic devices.

[0004] This object is achieved by providing an invention of a novel organic molecule.

[0005] The inventive organic molecules are purely organic molecules, ie, in contrast to the known metal complexes used in optoelectronic devices, the organic molecules do not contain any metal ions.

[0006] The organic molecules according to the invention exhibit an emission maximum in the deep blue, sky blue, green, or yellow spectral range (preferably in the deep blue, sky blue, and green spectral ranges, and most preferably in the deep blue or green spectral range). Specifically, the organic molecules exhibit an emission maximum between 420 nm and 580 nm (more preferably between 440 nm and 560 nm, even more preferably between 440 nm and 480 nm, or between 500 nm and 550 nm, and most preferably between 450 nm and 470 nm, or between 520 nm and 540 nm). The photoluminescence quantum yield of the organic molecules according to the invention is preferably equal to or higher than 10%, more preferably equal to or higher than 20%, even more preferably equal to or higher than 30%, even more preferably equal to or higher than 40%, and particularly preferably equal to or higher than 50%. Specifically, the organic molecules according to the invention exhibit thermally activated delayed fluorescence (TADF). The use of the organic molecules according to the invention in optoelectronic devices (e.g., organic light-emitting diodes (OLEDs)) results in higher efficiency of the optoelectronic devices. The corresponding OLEDs have higher stability and comparable colors than OLEDs with known emitter materials, and / or by employing the organic molecules according to the invention in OLED displays, a more accurate reproduction of the visible colors is achieved, i.e., a higher resolution of the displayed image. In particular, the organic molecules can be used in combination with fluorescent emitters to enable so-called superfluorescence.

[0007] The organic molecule according to the invention comprises or consists of a first chemical moiety and a second chemical moiety,

[0008] The first chemical moiety comprises or consists of a structure of Formula Ia or Formula Ib:

[0009]

[0010] The second chemical moiety comprises or consists of a structure of Formula II:

[0011]

[0012] in,

[0013] The first chemical moiety is linked to the second chemical moiety via a single bond.

[0014] T is a binding site for a single bond connecting the first chemical moiety to the second chemical moiety, or is selected from the group consisting of R 2 and R X The group composed of.

[0015] V is the binding site of a single bond connecting the first chemical moiety to the second chemical moiety, or hydrogen (H).

[0016] W is a binding site for a single bond connecting the first chemical moiety to the second chemical moiety, or is selected from the group consisting of R 2 and R X The group composed of.

[0017] X is selected from R 2 and R X The group composed of.

[0018] Y is selected from R 2 and R X The group composed of.

[0019] R X Selected from CN and CF3, or R X comprising or consisting of a structure of formula BN-I,

[0020]

[0021] The structure of Formula BN-I is bound to the structure of Formula Ia or Formula Ib via a single bond indicated by a dotted line, wherein exactly one R BN The group is CN, and the other two R BN Both groups are hydrogen (H), that is, in R X When represented by Formula BN-I, Formula BN-I includes or consists of a structure according to any one of Formula BN-Ia, Formula BN-Ib, and Formula BN-1-c:

[0022]

[0023] R 1 Selected from the group consisting of: hydrogen; deuterium; OR 3 ;Si(R 3 )3;B(OR 3 )2;OSO2R 3 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl, optionally substituted with one or more substituents R 3 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 3 C=CR 3 、C≡C、Si(R 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 、P(=O)(R 3 ), SO, SO2, NR 3 , O, S, or CONR 3 Substitution; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 3 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 3 C=CR 3 、C≡C、Si(R 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 、P(=O)(R 3 ), SO, SO2, NR 3 , O, S, or CONR 3 Substitution; C1-C 40 Thioalkoxy, optionally substituted with one or more substituents R 3 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 3 C=CR 3 、C≡C、Si(R 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 、P(=O)(R 3 ), SO, SO2, NR 3 , O, S, or CONR 3 Substitution; C2-C 40Alkenyl, optionally substituted with one or more substituents R 3 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 3 C=CR 3 、C≡C、Si(R 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 、P(=O)(R 3 ), SO, SO2, NR 3 , O, S, or CONR 3 Substitution; C2-C 40 Alkynyl, optionally substituted with one or more substituents R 3 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 3 C=CR 3 、C≡C、Si(R 3 )2、Ge(R 3 )2、Sn(R 3 )2. C=O, C=S, C=Se, C=NR 3 、P(=O)(R 3 ), SO, SO2, NR 3 , O, S, or CONR 3 Substitution; and C6-C 60 Aryl, optionally substituted with one or more substituents R 3 .

[0024] R 3 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 4 )2;OR 4 ;Si(R 4 )3;B(OR 4 )2;OSO2R 4 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl, optionally substituted with one or more substituents R 4 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 4 C=CR 4 、C≡C、Si(R 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 ), SO, SO2, NR 4, O, S, or CONR 4 Substitution; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 4 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 4 C=CR 4 、C≡C、Si(R 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 ), SO, SO2, NR 4 , O, S, or CONR 4 Substitution; C1-C 40 Thioalkoxy, optionally substituted with one or more substituents R 4 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 4 C=CR 4 、C≡C、Si(R 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 ), SO, SO2, NR 4 , O, S, or CONR 4 Substitution; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 4 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 4 C=CR 4 、C≡C、Si(R 4 )2、Ge(R 4 )2、Sn(R 4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 ), SO, SO2, NR 4 , O, S, or CONR 4 Substitution; C2-C 40 Alkynyl, optionally substituted with one or more substituents R 4 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 4 C=CR 4 、C≡C、Si(R 4 )2、Ge(R 4 )2、Sn(R4 )2. C=O, C=S, C=Se, C=NR 4 、P(=O)(R 4 ), SO, SO2, NR 4 , O, S, or CONR 4 Substitution; C6-C 60 Aryl, optionally substituted with one or more substituents R 4 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 4 .

[0025] R 2 are independently selected from the group consisting of: hydrogen; deuterium; C1-C 10 Alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C2-C 10 Alkenyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C2-C 10 Alkynyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C5-C 10 Aryl, wherein one or more hydrogen atoms are optionally replaced by a group R 5 replace.

[0026] Optionally, the two moieties R included in the first chemical moiety b Combined and together form a selection from direct bond, CR 6 R 7 、C=CR 6 R 7 、C=O、C=NR 6 NR 6 、O、SiR 6 R 7 , S, S(O) and S(O)2.

[0027] R a 、R b 、R c 、R d 、R 6 and R 7 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 8 )2;OR 8 ;Si(R 8 )3;B(OR 8 )2;OSO2R 8 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl, optionally substituted with one or more substituents R 8, and wherein one or more non-adjacent CH2 groups are optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 )2、Ge(R 8 )2、Sn(R 8 )2. C=O, C=S, C=Se, C=NR 8 、P(=O)(R 8 ), SO, SO2, NR 8 , O, S, or CONR 8 Substitution; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 )2、Ge(R 8 )2、Sn(R 8 )2. C=O, C=S, C=Se, C=NR 8 、P(=O)(R 8 ), SO, SO2, NR 8 , O, S, or CONR 8 Substitution; C1-C 40 Thioalkoxy, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 )2、Ge(R 8 )2、Sn(R 8 )2. C=O, C=S, C=Se, C=NR 8 、P(=O)(R 8 ), SO, SO2, NR 8 , O, S, or CONR 8 Substitution; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 )2、Ge(R 8 )2、Sn(R 8 )2. C=O, C=S, C=Se, C=NR 8 、P(=O)(R 8 ), SO, SO2, NR8 , O, S, or CONR 8 Substitution; C2-C 40 Alkynyl, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 )2、Ge(R 8 )2、Sn(R 8 )2. C=O, C=S, C=Se, C=NR 8 、P(=O)(R 8 ), SO, SO2, NR 8 , O, S, or CONR 8 Substitution; C6-C 60 Aryl, optionally substituted with one or more substituents R 8 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 8 .

[0028] R 8 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 9 )2;OR 9 ;Si(R 9 )3;B(OR 9 )2;OSO2R 9 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl, optionally substituted with one or more substituents R 9 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 9 C=CR 9 、C≡C、Si(R 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 、P(=O)(R 9 ), SO, SO2, NR 9 , O, S, or CONR 9 Substitution; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 9 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 9 C=CR 9 、C≡C、Si(R 9 )2、Ge(R9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 、P(=O)(R 9 ), SO, SO2, NR 9 , O, S, or CONR 9 Substitution; C1-C 40 Thioalkoxy, optionally substituted with one or more substituents R 9 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 9 C=CR 9 、C≡C、Si(R 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 、P(=O)(R 9 ), SO, SO2, NR 9 , O, S, or CONR 9 Substitution; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 9 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 9 C=CR 9 、C≡C、Si(R 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 、P(=O)(R 9 ), SO, SO2, NR 9 , O, S, or CONR 9 Substitution; C2-C 40 Alkynyl, optionally substituted with one or more substituents R 9 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 9 C=CR 9 、C≡C、Si(R 9 )2、Ge(R 9 )2、Sn(R 9 )2. C=O, C=S, C=Se, C=NR 9 、P(=O)(R 9 ), SO, SO2, NR 9 , O, S, or CONR 9 Substitution; C6-C 60 Aryl, optionally substituted with one or more substituents R 9; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 9 .

[0029] Optionally, the substituent R a 、R b 、R c 、R d 、R 6 、R 7 and R 8 Any one of which is independently selected from R a 、R b 、R c 、R d 、R 6 、R 7 and R 8 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the additional rings optionally so formed may be optionally substituted with one or more substituents R 10 .

[0030] # indicates the binding site of the first chemical moiety and the second chemical moiety.

[0031] Z is selected from the direct bond, CR 11 R 12 、C=CR 11 R 12 、C=O、C=NR 11 NR 11 、O、SiR 11 R 12 , S, S(O) and S(O)2.

[0032] R e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 13 )2;OR 13 ;Si(R 13 )3;B(OR 13 )2;OSO2R 13 ;CF3;CN;F;Cl;Br;I;C1-C 40 Alkyl, optionally substituted with one or more substituents R 13 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 13 C=CR 13 、C≡C、Si(R 13)2、Ge(R 13 )2、Sn(R 13 )2. C=O, C=S, C=Se, C=NR 13 、P(=O)(R 13 ), SO, SO2, NR 13 , O, S, or CONR 13 Substitution; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 13 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 13 C=CR 13 、C≡C、Si(R 13 )2、Ge(R 13 )2、Sn(R 13 )2. C=O, C=S, C=Se, C=NR 13 、P(=O)(R 13 ), SO, SO2, NR 13 , O, S, or CONR 13 Substitution; C1-C 40 Thioalkoxy, optionally substituted with one or more substituents R 13 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 13 C=CR 13 、C≡C、Si(R 13 )2、Ge(R 13 )2、Sn(R 13 )2. C=O, C=S, C=Se, C=NR 13 、P(=O)(R 13 ), SO, SO2, NR 13 , O, S, or CONR 13 Substitution; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 13 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 13 C=CR 13 、C≡C、Si(R 13 )2、Ge(R 13 )2、Sn(R 13 )2. C=O, C=S, C=Se, C=NR 13 、P(=O)(R 13 ), SO, SO2, NR 13 , O, S, or CONR 13 Substitution; C2-C 40 Alkynyl, optionally substituted with one or more substituents R13 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 13 C=CR 13 、C≡C、Si(R 13 )2、Ge(R 13 )2、Sn(R 13 )2. C=O, C=S, C=Se, C=NR 13 、P(=O)(R 13 ), SO, SO2, NR 13 , O, S, or CONR 13 Substitution; C6-C 60 Aryl, optionally substituted with one or more substituents R 13 ; and C3-C 60 Heteroaryl, optionally substituted with one or more substituents R 13 .

[0033] R 13 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 14 )2;OR 14 ;Si(R 14 )3;B(OR 14 )2;OSO2R 14 ;CF3;CN;F;Br;I;C1-C 40 Alkyl, optionally substituted with one or more substituents R 14 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 14 C=CR 14 、C≡C、Si(R 14 )2、Ge(R 14 )2、Sn(R 14 )2. C=O, C=S, C=Se, C=NR 14 、P(=O)(R 14 ), SO, SO2, NR 14 , O, S, or CONR 14 Substitution; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 14 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 14 C=CR 14 、C≡C、Si(R 14 )2、Ge(R 14 )2、Sn(R 14 )2. C=O, C=S, C=Se, C=NR 14 、P(=O)(R 14), SO, SO2, NR 14 , O, S, or CONR 14 Substitution; C1-C 40 Thioalkoxy, optionally substituted with one or more substituents R 14 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 14 C=CR 14 、C≡C、Si(R 14 )2、Ge(R 14 )2、Sn(R 14 )2. C=O, C=S, C=Se, C=NR 14 、P(=O)(R 14 ), SO, SO2, NR 14 , O, S, or CONR 14 Substitution; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 14 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 14 C=CR 14 、C≡C、Si(R 14 )2、Ge(R 14 )2、Sn(R 14 )2. C=O, C=S, C=Se, C=NR 14 、P(=O)(R 14 ), SO, SO2, NR 14 , O, S, or CONR 14 Substitution; C2-C 40 Alkynyl, optionally substituted with one or more substituents R 14 , and wherein one or more non-adjacent CH2 groups are optionally replaced by R 14 C=CR 14 、C≡C、Si(R 14 )2、Ge(R 14 )2、Sn(R 14 )2. C=O, C=S, C=Se, C=NR 14 、P(=O)(R 14 ), SO, SO2, NR 14 , O, S, or CONR 14 Substitution; C6-C 60 Aryl, optionally substituted with one or more substituents R 14 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 14 .

[0034] Optionally, the substituent Re 、R f 、R g 、R 11 、R 12 and R 13 Any one of which is independently selected from R e 、R f 、R g 、R 11 、R 12 and R 13 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the additional rings optionally so formed may be optionally substituted with one or more substituents R 15 .

[0035] R 4 、R 9 、R 10 、R 14 and R 15 is selected at each occurrence, independently of one another, from the group consisting of: hydrogen; deuterium; OPh (Ph = phenyl); CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, Ph or C1-C5 alkyl; N(C6-C 18 Aryl)2; N(C3-C 17 heteroaryl)2; and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0036] R 5is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally replaced, independently of one another, by deuterium, CN, CF3 or F; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, Ph or C1-C5 alkyl; N(C6-C 18 Aryl)2; N(C3-C 17 heteroaryl)2; and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0037] According to the invention, exactly one substituent selected from the group consisting of T, W, X and Y is R X , and exactly one substituent selected from the group consisting of T, V and W represents the binding site of the single bond connecting the first chemical moiety and the second chemical moiety.

[0038] Furthermore, according to the invention, if T is R X and V is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, then W is hydrogen (H).

[0039] Having R 1 Formula Ia yields Formula Ib.

[0040] In a specific embodiment of the invention, T is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and W is R X .

[0041] In a preferred embodiment of the invention, T is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and X is R X .

[0042] In a specific embodiment of the invention, T is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and Y is R X .

[0043] In a specific embodiment of the invention, V is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and T is R X .

[0044] In a specific embodiment of the invention, V is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and W is R X .

[0045] In a specific embodiment of the invention, V is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and X is R X .

[0046] In a specific embodiment of the invention, V is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and Y is R X .

[0047] In a specific embodiment of the invention, W is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and T is R X .

[0048] In a preferred embodiment of the invention, W is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and X is R X .

[0049] In a specific embodiment of the invention, W is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, and Y is R X .

[0050] In a specific embodiment of the invention, R X comprising or consisting of a structure of formula BN-I.

[0051] In a specific embodiment of the invention, R X comprising or consisting of a structure of formula BN-Ia.

[0052] In a specific embodiment of the invention, R X comprising or consisting of a structure of formula BN-Ib.

[0053] In a specific embodiment of the invention, R X comprising or consisting of a structure of formula BN-Ic.

[0054] In a specific embodiment of the invention, R X It's CF3.

[0055] In a preferred embodiment of the invention, R X It is CN.

[0056] In one embodiment of the invention, in the first chemical moiety,

[0057] R 1 Selected from the group consisting of: hydrogen; deuterium; OR 3 ;Si(R 3 )3; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 3 ; and C6-C 18 Aryl, optionally substituted with one or more substituents R 3 ;

[0058] R 3 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 4 )2;OR 4 ;Si(R 4 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 4 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 4 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 4 ;

[0059] R 2 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced by a group R 5 replace;

[0060] Among them, the two parts R included in the first chemical part b optionally combined and together formed from a combination of direct bonds, CR 6 R 7 、C=CR 6 R 7 、C=O、C=NR 6 NR 6 、O、SiR 6 R 7 , S, S(O) and S(O)2;

[0061] R a 、R b 、R c 、R d 、R 6 and R 7are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 8 )2;OR 8 ;Si(R 8 )3; F; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 8 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 8 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 8 ;

[0062] R 8 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 9 )2;OR 9 ;Si(R 9 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 9 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 9 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 9 ;

[0063] Wherein, optionally, the substituent R a 、R b 、R c 、R d 、R 6 、R 7 and R 8 Any one of which is independently selected from R a 、R b 、R c 、R d 、R 6 、R 7 and R 8 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of formula Ia or formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;

[0064] R 4 、R 9 and R 10 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN;

[0065] R 5 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally replaced independently of one another by deuterium, C1-C5 alkyl, Ph or CN.

[0066] In a preferred embodiment of the invention, in the first chemical moiety,

[0067] R 1 Selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, optionally substituted with one or more substituents R 3 ; and C6-C 18 Aryl, optionally substituted with one or more substituents R 3 ;

[0068] R 3 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(Ph)2; OPh; Si(Me)3; Si(Ph)3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 4 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 4 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 4 ;

[0069] R 2is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced by a group R 5 replace;

[0070] Among them, the two parts R included in the first chemical part b Optionally combined and together form a group consisting of a direct bond, C=O, NR 6 、O、SiR 6 R 7 , S, S(O) and S(O)2;

[0071] R a 、R b 、R c 、R d 、R 6 and R 7 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; Si(Me)3; Si(Ph)3; N(Ph)2; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 8 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 8 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 8 ;

[0072] R 8 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; Si(Me)3; Si(Ph)3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 9 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 9 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 9 ;

[0073] Wherein, optionally, the substituent R a 、R b 、R c 、R d 、R 6 、R 7 and R 8 Any one of which is independently selected from R a 、R b 、Rc 、R d 、R 6 、R 7 and R 8 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of the corresponding benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of Formula Ia or Formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;

[0074] R 4 、R 9 and R 10 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN;

[0075] R 5 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution.

[0076] In an even more preferred embodiment of the invention, in the first chemical moiety,

[0077] R 1 Selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, optionally substituted with one or more substituents R 3; and C6-C 18 Aryl, optionally substituted with one or more substituents R 3 ;

[0078] R 3 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(Ph)2; OPh; Si(Me)3; Si(Ph)3; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium, independently of each other; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution;

[0079] R 2 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu or Ph substitution;

[0080] Among them, the two parts R included in the first chemical part b are optionally combined and together form a group Y which is a direct bond at each occurrence;

[0081] R a 、R b 、R c and R d is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; CF3; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted independently of each other by deuterium, CN, CF3, F or Ph; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substituted; pyridyl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substituted; pyrimidinyl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substituted; carbazolyl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, tBu, CF3, CN or Ph substituted; and triazine groups, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substitution;

[0082] Wherein, optionally, the substituent R a 、R b 、R c and R d Any one of which is independently selected from R a 、R b 、R c and R d wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of the corresponding benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of Formula Ia or Formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;

[0083] R 10 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; Me; i Pr; t Bu; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0084] In an even more preferred embodiment of the invention, in the first chemical moiety,

[0085] R 1 Selected from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, optionally substituted with one or more substituents R 3 ; and C6-C 18 Aryl, optionally substituted with one or more substituents R 3 ;

[0086] R 3is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(Ph)2; OPh; Si(Me)3; Si(Ph)3; CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium, independently of each other; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution;

[0087] R 2 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C6-C 18 Aryl; wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu or Ph substitution;

[0088] Among them, the two parts R included in the first chemical part b are optionally combined and together form a group Y which is a direct bond at each occurrence;

[0089] R a 、R b 、R c and R d is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; CF3; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally replaced independently of one another by deuterium, CN, CF3, F or Ph; Ph, wherein one or more hydrogen atoms are optionally replaced independently of one another by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substituted; carbazolyl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substituted; and triazine groups, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substitution;

[0090] Wherein, optionally, the substituent R a 、R b 、R c and R d Any one of which is independently selected from R a 、R b 、R c and R dwherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of the corresponding benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of Formula Ia or Formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;

[0091] R 10 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0092] In an even more preferred embodiment of the invention, in the first chemical moiety,

[0093] R 1 selected from the group consisting of: hydrogen; deuterium; Me; i Pr, t Bu; and Ph, optionally substituted with one or more substituents R 3 ;

[0094] R 3 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution;

[0095] R 2 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu or Ph substitution;

[0096] Among them, the two parts R included in the first chemical part bare optionally combined and together form a group Y which is a direct bond at each occurrence;

[0097] R a 、R b 、R c and R d are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; CF3; N(Ph)2; Me; i Pr; t Bu; Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substituted; and carbazolyl, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substitution;

[0098] Wherein, optionally, the substituent R a 、R b 、R c and R d Any one of which is independently selected from R a 、R b 、R c and R d wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of the corresponding benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of Formula Ia or Formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;and

[0099] R 10 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; Me; i Pr; t Bu; Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0100] In an even more preferred embodiment of the invention, in the first chemical moiety,

[0101] R 1selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution;

[0102] R 2 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu or Ph substitution;

[0103] Among them, the two parts R included in the first chemical part b are optionally combined and together form a group Y which is a direct bond at each occurrence;

[0104] R a 、R b 、R c and R d are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CN or Ph substitution;

[0105] Wherein, optionally, the substituent R a 、R b 、R c and R d Any one of which is independently selected from R a 、R b 、R c and R d wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of the corresponding benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of Formula Ia or Formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;and

[0106] R 10 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0107] In a particularly preferred embodiment of the invention, in the first chemical moiety,

[0108] R 1 selected from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution;

[0109] R 2 are independently selected at each occurrence from hydrogen and deuterium;

[0110] Among them, the two parts R included in the first chemical part b are optionally combined and together form a group Y which is a direct bond at each occurrence;

[0111] R a 、R b 、R c and R d are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CN or Ph substitution;

[0112] Wherein, optionally, the substituent R a 、R b 、R c and R d Any one of which is independently selected from R a 、R b 、R c and R dwherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system consisting of the corresponding benzene ring a, benzene ring b, benzene ring c, benzene ring d, benzene ring e or benzene ring f of Formula Ia or Formula Ib and the additional ring formed by the adjacent substituents comprises a total of 9 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 10 ;and

[0113] R 10 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0114] In one embodiment of the invention, none of the a 、R b 、R c 、R d 、R 6 、R 7 and R 8 The substituents in R a 、R b 、R c 、R d 、R 6 、R 7 and R 8 Any adjacent substituents in form an additional ring or ring system.

[0115] In one embodiment of the invention, R a 、R b 、R c and R d In every occurrence it is hydrogen.

[0116] In one embodiment of the invention, R a 、R c and R d is hydrogen at each occurrence, and the two radicals R b are combined and together form a group Y which is a direct bond at each occurrence.

[0117] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1, Formula Ib-1, Formula Ia-2, and Formula Ib-2:

[0118]

[0119] Therein, a dashed line represents a single bond connecting the first chemical moiety to the second chemical moiety, wherein, otherwise, the above definitions apply.

[0120] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1 and Formula Ia-2, wherein the above definitions apply.

[0121] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ib-1 and Formula Ib-2, wherein the above definitions apply.

[0122] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1 and Formula Ib-1, wherein the above definitions apply.

[0123] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-2 and Formula Ib-2, wherein the above definitions apply.

[0124] In a preferred embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-1-1, Formula Ib-1-1, Formula Ia-2-1, and Formula Ib-2-1, or consists of a structure according to any one of Formula Ia-1-1, Formula Ib-1-1, Formula Ia-2-1, and Formula Ib-2-1:

[0125]

[0126] Therein, a dashed line represents a single bond connecting the first chemical moiety to the second chemical moiety, wherein, otherwise, the above definitions apply.

[0127] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1-1 and Formula Ia-2-1, wherein the above definitions apply.

[0128] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ib-1-1 and Formula Ib-2-1, wherein the above definitions apply.

[0129] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1-1 and Formula Ib-1-1, wherein the above definitions apply.

[0130] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-2-1 and Formula Ib-2-1, wherein the above definitions apply.

[0131] In a preferred embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-1-1-a, Formula Ia-1-1-b, Formula Ib-1-1-a, Formula Ib-1-1-b, Formula Ia-2-1-a, Formula Ia-2-1-b, Formula Ib-2-1-a, and Formula Ib-2-1-b, or consists of a structure according to any one of Formula Ia-1-1-a, Formula Ia-1-1-b, Formula Ib-1-1-a, Formula Ib-1-1-b, Formula Ia-2-1-a, Formula Ia-2-1-b, Formula Ib-2-1-a, and Formula Ib-2-1-b:

[0132]

[0133]

[0134] Therein, a dashed line represents a single bond connecting the first chemical moiety to the second chemical moiety, wherein, otherwise, the above definitions apply.

[0135] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-1-1-a and Formula Ia-1-1-b, or consists of a structure according to any one of Formula Ia-1-1-a and Formula Ia-1-1-b, wherein the above definitions apply.

[0136] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ib-1-1-a and Formula Ib-1-1-b, wherein the above definitions apply.

[0137] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-2-1-a and Formula Ia-2-1-b, or consists of a structure according to any one of Formula Ia-2-1-a and Formula Ia-2-1-b, wherein the above definitions apply.

[0138] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ib-2-1-a and Formula Ib-2-1-b, or consists of a structure according to any one of Formula Ib-2-1-a and Formula Ib-2-1-b, wherein the above definitions apply.

[0139] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-1-1-a and Formula Ia-2-1-a, or consists of a structure according to any one of Formula Ia-1-1-a and Formula Ia-2-1-a, wherein the above definitions apply.

[0140] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ib-1-1-a and Formula Ib-2-1-a, or consists of a structure according to any one of Formula Ib-1-1-a and Formula Ib-2-1-a, wherein the above definitions apply.

[0141] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-1-1-a and Formula Ib-1-1-a, or consists of a structure according to any one of Formula Ia-1-1-a and Formula Ib-1-1-a, wherein the above definitions apply.

[0142] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-2-1-a and Formula Ib-2-1-a, or consists of a structure according to any one of Formula Ia-2-1-a and Formula Ib-2-1-a, wherein the above definitions apply.

[0143] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1-1-b and Formula Ia-2-1-b, wherein the above definitions apply.

[0144] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ib-1-1-b and Formula Ib-2-1-b, wherein the above definitions apply.

[0145] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to any one of Formula Ia-1-1-b and Formula Ib-1-1-b, wherein the above definitions apply.

[0146] In one embodiment of the invention, the first chemical moiety comprises a structure according to any one of Formula Ia-2-1-b and Formula Ib-2-1-b, or consists of a structure according to any one of Formula Ia-2-1-b and Formula Ib-2-1-b, wherein the above definitions apply.

[0147] In a preferred embodiment of the invention, the first chemical moiety includes a structure according to any one of Formula Ia-1-1-a, Formula Ib-1-1-a, Formula Ia-1-1-b and Formula Ib-1-1-b, or consists of a structure according to any one of Formula Ia-1-1-a, Formula Ib-1-1-a, Formula Ia-1-1-b and Formula Ib-1-1-b, wherein the above definitions apply.

[0148] In another preferred embodiment of the invention, the first chemical part includes a structure according to any one of Formula Ia-2-1-a, Formula Ib-2-1-a, Formula Ia-2-1-b and Formula Ib-2-1-b, or is composed of a structure according to any one of Formula Ia-2-1-a, Formula Ib-2-1-a, Formula Ia-2-1-b and Formula Ib-2-1-b, wherein the above definitions apply.

[0149] In one embodiment of the invention, the first chemical moiety includes a structure according to any one of Formula Ia-1-1-a, Formula Ia-1-1-b, Formula Ia-2-1-a and Formula Ia-2-1-b, or consists of a structure according to any one of Formula Ia-1-1-a, Formula Ia-1-1-b, Formula Ia-2-1-a and Formula Ia-2-1-b, wherein the above definitions apply.

[0150] In one embodiment of the invention, the first chemical moiety includes a structure according to any one of Formula Ib-1-1-a, Formula Ib-1-1-b, Formula Ib-2-1-a and Formula Ib-2-1-b, or is composed of a structure according to any one of Formula Ib-1-1-a, Formula Ib-1-1-b, Formula Ib-2-1-a and Formula Ib-2-1-b, wherein the above definitions apply.

[0151] In one embodiment of the invention, the first chemical moiety includes a structure according to any one of Formula Ia-1-1-a, Formula Ib-1-1-a, Formula Ia-2-1-a and Formula Ib-2-1-a, or is composed of a structure according to any one of Formula Ia-1-1-a, Formula Ib-1-1-a, Formula Ia-2-1-a and Formula Ib-2-1-a, wherein the above definitions apply.

[0152] In one embodiment of the invention, the first chemical moiety includes a structure according to any one of Formula Ia-1-1-b, Formula Ib-1-1-b, Formula Ia-2-1-b and Formula Ib-2-1-b, or consists of a structure according to any one of Formula Ia-1-1-b, Formula Ib-1-1-b, Formula Ia-2-1-b and Formula Ib-2-1-b, wherein the above definitions apply.

[0153] In one embodiment of the invention, the second chemical moiety R e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 13 )2;OR 13 ;Si(R 13 )3; F; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 13 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 13 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 13 ;

[0154] R 13 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 14 )2;OR 14 ;Si(R 14 )3; CF3; CN; F; C1-C5 alkyl, optionally substituted with one or more substituents R 14;C6-C 18 Aryl, optionally substituted with one or more substituents R 14 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 14 ;

[0155] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 、R 12 and R 13 Any one of which is independently selected from R e 、R f 、R g 、R 11 、R 12 and R 13 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0156] R 14 and R 15 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally replaced independently of one another by deuterium, C1-C5 alkyl, Ph or CN.

[0157] In one embodiment of the invention, the second chemical moiety R e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 8 )2;OR 8 ;Si(R 8)3; F; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 13 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 13 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 13 ;

[0158] R 13 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN;

[0159] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0160] R 15 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN.

[0161] In one embodiment of the invention, the second chemical moiety R e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 8 )2;OR 8 ;Si(R 8 )3; F; CF3; CN; C1-C5 alkyl, optionally substituted with one or more substituents R 13 ;C6-C 18 Aryl, optionally substituted with one or more substituents R 13 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 13 ;

[0162] R 13 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CF3; CN; F; N(Ph)2; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally substituted independently of one another by deuterium, C1-C5 alkyl, Ph or CN;

[0163] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0164] R 15is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; OPh; CF3; CN; F; N(Ph)2; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; and C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution.

[0165] In a preferred embodiment of the invention, the second chemical moiety R e 、R f 、R g 、R 11 and R 12 independently of one another at each occurrence selected from the group consisting of: hydrogen; deuterium; N(Ph)2; OPh; Si(Me)3; Si(Ph)3; F; CF3; CN; C6-C 18 Aryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substitution; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substitution;

[0166] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12 wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0167] R 15are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution.

[0168] In an even more preferred embodiment of the invention, R of the second chemical moiety e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; N(Ph)2; Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substituted; pyridyl, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substituted; pyrimidinyl, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substituted; carbazolyl, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substituted; and triazine groups in which one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substitution;

[0169] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0170] R 15 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu, Ph or CN substitution.

[0171] In an even more preferred embodiment of the invention, R of the second chemical moiety e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; N(Ph)2; Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substituted; carbazolyl, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substituted; and triazine groups in which one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, CF3 and Ph substitution;

[0172] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0173] R 15 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0174] In an even more preferred embodiment of the invention, R of the second chemical moiety e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; N(Ph)2; Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN and Ph substituted; and carbazolyl groups in which one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, and Ph substitutions;

[0175] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, wherein 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0176] R 15 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0177] In an even more preferred embodiment of the invention, R of the second chemical moiety e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; CN; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu, CN, and Ph substitutions;

[0178] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0179] R 15 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced independently of each other by deuterium, Me, i Pr, t Bu or Ph substituted.

[0180] In a particularly preferred embodiment of the invention, the second chemical moiety R e 、R f 、R g 、R 11 and R 12 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu and Ph substitution;

[0181] Wherein, optionally, the substituent R e 、R f 、R g 、R 11 and R 12 Any one of which is independently selected from R e 、R f 、R g 、R 11 and R 12wherein one or more adjacent substituents form a monocyclic or polycyclic aliphatic or aromatic carbocyclic or heterocyclic and / or benzo-fused ring or ring system; wherein the optionally so-formed fused ring system constructed from the structure according to formula II (counting a total of 13 or 14 ring atoms, depending on the nature of Z) and the additional ring formed by the adjacent substituents comprises a total of 16 to 30 ring atoms, of which 1 to 3 atoms may be heteroatoms independently selected from nitrogen (N), oxygen (O) and sulfur (S); and wherein the optionally so-formed additional ring may be optionally substituted with one or more substituents R 15 ;

[0182] R 15 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph.

[0183] In one embodiment of the invention, R e is hydrogen at each occurrence, or as described above with a member selected from R e 、R f 、R g 、R 11 and R 12 Adjacent substituents in form additional rings or ring systems.

[0184] In a preferred embodiment of the invention, the second chemical moiety comprises or consists of a structure of formula II-a:

[0185]

[0186]

[0187] Therein, the above definitions apply.

[0188] In one embodiment of the invention, the second chemical moiety comprises a structure according to any one of formula II-a-1, formula II-a-2, formula II-a-3, formula II-a-4, formula II-a-5, formula II-a-6, formula II-a-7, formula II-a-8, formula II-a-9, formula II-a-10, formula II-a-11, formula II-a-12, formula II-a-13, formula II-a-14, and formula II-a-15, or consists of a structure according to any one of formula II-a-1, formula II-a-2, formula II-a-3, formula II-a-4, formula II-a-5, formula II-a-6, formula II-a-7, formula II-a-8, formula II-a-9, formula II-a-10, formula II-a-11, formula II-a-12, formula II-a-13, formula II-a-14, and formula II-a-15:

[0189]

[0190] in,

[0191] X is selected from the group consisting of C(R 16 )2、NR 16 , O and S;

[0192] R 16 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu and Ph are substituted.

[0193] In a preferred embodiment of the invention, the second chemical moiety comprises a structure according to any one of formula II-a-1, formula II-a-5, formula II-a-9, formula II-a-10, formula II-a-11, formula II-a-12, formula II-a-13, formula II-a-14 and formula II-a-15, or consists of a structure according to any one of formula II-a-1, formula II-a-5, formula II-a-9, formula II-a-10, formula II-a-11, formula II-a-12, formula II-a-13, formula II-a-14 and formula II-a-15:

[0194]

[0195] in,

[0196] X is selected from C(R 16 )2、NR 16 , O and S;

[0197] R 16 are independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu and Ph are substituted.

[0198] In one embodiment of the invention, the second chemical moiety comprises or consists of a structure according to formula II-a-1, wherein the above definitions apply.

[0199] In one embodiment of the invention, the second chemical moiety comprises or consists of a structure according to formula II-a-5, wherein the above definitions apply.

[0200] In a preferred embodiment of the invention, the second chemical moiety comprises or consists of a structure according to formula II-a-1 or formula II-a-5, wherein the above definitions apply.

[0201] Below, an example of a second chemical part is shown:

[0202]

[0203]

[0204] This does not, however, imply that the present invention is limited to organic molecules comprising a second chemical moiety represented by any of the exemplary structures shown above. BRIEF DESCRIPTION OF THE DRAWINGS

[0205] Figure 1 is the emission spectrum of Example 1 (10 wt %) in PMMA.

[0206] Figure 2 is the emission spectrum of Example 2 (10 wt %) in PMMA.

[0207] Figure 3 is the emission spectrum of Example 3 (10 wt %) in PMMA.

[0208] Figure 4 is the emission spectrum of Example 4 (10 wt %) in PMMA.

[0209] Figure 5 is the emission spectrum of Example 5 (10 wt %) in PMMA.

[0210] Figure 6 is the emission spectrum of Example 6 (10 wt %) in PMMA.

[0211] Figure 7 is the emission spectrum of Example 7 (10 wt %) in PMMA.

[0212] Figure 8 is the emission spectrum of Example 8 (10 wt %) in PMMA.

[0213] Figure 9 is the emission spectrum of Example 9 (10 wt %) in PMMA.

[0214] Figure 10 is the emission spectrum of Example 10 (10 wt %) in PMMA.

[0215] Figure 11 is the emission spectrum of Example 11 (10 wt %) in PMMA.

[0216] Figure 12 is the emission spectrum of Example 12 (10 wt %) in PMMA.

[0217] Figure 13 is the emission spectrum of Example 13 (10 wt %) in PMMA. DETAILED DESCRIPTION

[0218] As used throughout this application, the term "cyclic group" may be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0219] As used throughout this application, the terms "ring" and "ring system" may be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0220] The term "ring atom" refers to any atom that is part of the core of a ring or ring structure and not part of a substituent optionally attached to the core.

[0221] As used throughout this application, the term "carbocycle" may be understood in the broadest sense as any cyclic group wherein the core structure comprises only carbon atoms, which may of course be substituted with hydrogen or any other substituents as defined in the specific embodiments of the invention. It is understood that the term "carbocycle" as an adjective refers to a cyclic group wherein the core structure comprises only carbon atoms, which may of course be substituted with hydrogen or any other substituents as defined in the specific embodiments of the invention.

[0222] As used throughout this application, the term "heterocycle" can be understood in the broadest sense as any cyclic group wherein the ring core structure not only includes carbon atoms but also includes at least one heteroatomic. It is understood that the term "heterocycle" as an adjective refers to a cyclic group wherein the ring core structure not only includes carbon atoms but also includes at least one heteroatomic. Unless otherwise specified in a specific embodiment, heteroatoms can be identical or different at each occurrence and can be individually selected from the group consisting of N, O and S. All carbon atoms or heteroatoms included in the heterocycle in the context of the invention can certainly be substituted with hydrogen or any other substituent defined in a specific embodiment of the invention.

[0223] As used throughout this application, the term "aromatic ring system" may be understood in the broadest sense as any bicyclic or polycyclic aromatic moiety.

[0224] As used throughout this application, the term "heteroaromatic ring system" may be understood in the broadest sense as any bicyclic or polycyclic heteroaromatic moiety.

[0225] As used throughout this application, the term "fused" means that the aromatic ring or heteroaromatic ring of "fused" share at least one key when relating to an aromatic ring system or heteroaromatic ring system, and the at least one key is a part of two ring systems. For example, naphthalene (or naphthyl when being referred to as a substituent) or benzothiophene (or benzothiophene when being referred to as a substituent) are considered to be fused aromatic ring systems in the context of the present invention, wherein, two benzene rings (for naphthalene) or thiophene and benzene (for benzothiophene) share a key. It is also understood that in this context, sharing a key includes sharing two atoms that constitute the corresponding key, and the aromatic ring system or heteroaromatic ring system that is fused can be understood as an aromatic system or heteroaromatic system. In addition, it is understood that the aromatic ring or heteroaromatic ring that can be formed to be fused greater than a key can be shared (for example, in pyrene) by the aromatic ring or heteroaromatic ring that constitutes the aromatic ring system or heteroaromatic ring system. In addition, it will be understood that alicyclic ring systems can also be fused, and this has the same implication as for aromatic ring systems or heteroaromatic ring systems, except that the alicyclic ring system that is fused is certainly not aromatic.

[0226] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense to mean any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, unless otherwise specified in a specific embodiment of the invention, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this application, the number of aromatic ring carbon atoms may be given as a subscript number in the definition of certain substituents. Specifically, a heteroaromatic ring contains one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense to mean any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom. Unless otherwise specified in a specific embodiment, the heteroatoms may be the same or different at each occurrence and may be individually selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent having two points of attachment to other molecular structures and thus serving as a linker structure. In the event that a group in the exemplary embodiments is defined differently from the definition given herein (e.g., the number of aromatic ring atoms or the number of heteroatoms is different from the given definition), the definition in the exemplary embodiments will apply. According to the invention, a condensed (cyclized) aromatic polycyclic or heteroaromatic polycyclic ring is composed of two or more monoaromatic or heteroaromatic rings that form a polycyclic ring via a condensation reaction.

[0227] Specifically, as used throughout this application, the term "aryl" or "heteroaryl" includes groups that can be bonded via any position of an aromatic group or a heteroaromatic group, the group being derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, , perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthimidazole, pyridimidazole, pyrazinimidazole, quinoxalinoimidazole, oxadiazole oxazole, benzoxazole, naphthoxazole, anthraxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or a combination of the foregoing groups.

[0228] In certain embodiments of the invention, the adjacent substituents that are attached to an aromatic ring or ring system or heteroaromatic ring or ring system can together form an additional monocyclic or polycyclic aliphatic or aromatic carbocycle or heterocycle or ring system that is fused to the aromatic ring or ring system or heteroaromatic ring or ring system to which the substituent is attached. It is understood that the fused ring system optionally formed in this way will be larger (meaning that it includes more ring atoms) than the aromatic ring or ring system or heteroaromatic ring or ring system to which the adjacent substituent is attached. In these cases, the "total" amount of the ring atoms included in the fused ring system will be understood to be the sum of the ring atoms included in the aromatic ring or ring system or heteroaromatic ring or ring system to which the adjacent substituent is attached and the additional ring system formed by the adjacent substituent, but, wherein, the carbon atoms shared by the fused ring are counted once rather than twice. For example, a benzene ring can have two adjacent substituents that form another benzene ring to constitute a naphthalene core. Since two carbon atoms are shared by two benzene rings and are therefore counted only once rather than twice, the naphthalene nucleus then comprises 10 ring atoms.The term "adjacent substituents" in this context refers to substituents which are attached to the same or adjacent atoms.

[0229] As used throughout this application, the term "adjacent substituents" or "adjacent groups" refers to substituents or groups that are bound to the same or adjacent atoms.

[0230] As used throughout this application, the term "aliphatic" when referring to a ring system is to be understood in the broadest sense and means that there are no aromatic or heteroaromatic rings among the rings comprising the ring system. It is understood that such an aliphatic ring system can be fused to one or more aromatic rings such that some (but not all) of the carbon atoms or heteroatoms included in the core structure of the aliphatic ring system are part of the attached aromatic ring.

[0231] As used above and herein, the term "alkyl" may be understood in the broadest sense as any linear, branched or cyclic alkyl substituent. Specifically, the term alkyl includes such substituents as methyl (Me), ethyl (Et), n-propyl ( n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1- Bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hexan-1-yl, 1,1-dimethyl-n-heptan-1-yl, 1,1-dimethyl-n-octan-1-yl, 1,1-dimethyl-n-decan-1-yl, 1,1-dimethyl-n-dodecan-1-yl, 1,1-dimethyl-n-tetradecan-1-yl, 1,1-dimethyl-n-hexadecan-1-yl, 1,1-dimethyl-n-octadecan-1-yl, 1,1-diethyl-n-hexan-1-yl, 1,1-diethyl-n-heptan-1-yl, 1,1-diethyl-n-octan-1-yl, 1,1-diethyl-n-decan-1-yl, 1,1-diethyl-n- dodec-1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohexan-1-yl, 1-(n-butyl)-cyclohexan-1-yl, 1-(n-hexyl)-cyclohexan-1-yl, 1-(n-octyl)-cyclohexan-1-yl and 1-(n-decyl)-cyclohexan-1-yl.

[0232] As used above and herein, the term "alkenyl" includes straight chain, branched, and cyclic alkenyl substituents. The term alkenyl illustratively includes such substituents: vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0233] As used above and herein, the term "alkynyl" includes linear, branched, and cyclic alkynyl substituents. The term alkynyl illustratively includes ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.

[0234] As used above and herein, the term "alkoxy" includes linear, branched, and cyclic alkoxy substituents. The term alkoxy illustratively includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and 2-methylbutoxy.

[0235] As used above and herein, the term "thioalkoxy" includes straight chain, branched chain, and cyclic thioalkoxy substituents wherein the O of the exemplary alkoxy group is replaced by S.

[0236] As used above and herein, the terms "halogen" and "halo" may be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0237] It is understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it is a fragment (e.g., naphthyl, dibenzofuranyl) or as if it is the entire molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0238] All hydrogen atoms (H) included in any structure mentioned herein may be replaced by deuterium (D) at each occurrence, independently of each other, and not otherwise specified. The replacement of hydrogen with deuterium is customary and obvious to those skilled in the art.

[0239] In one embodiment of the invention, the organic molecules according to the invention have an excited state lifetime of no more than 50 μs (preferably no more than 25 μs, more preferably no more than 15 μs, even more preferably no more than 10 μs, even more preferably no more than 8 μs, or no more than 6 μs, particularly preferably no more than 4 μs) in a film of poly(methyl methacrylate) (PMMA) using 10 wt% of the organic molecules at room temperature.

[0240] In one embodiment of the invention, the organic molecules according to the invention exhibit a wavelength less than 5000 cm -1 (Preferably less than 3000cm -1, more preferably less than 1500cm -1 , even more preferably less than 1000 cm -1 , or even less than 500cm -1 ) of ΔE ST The value of thermally activated delayed fluorescence (TADF) emitter, ΔE ST The value corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1).

[0241] In yet another embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible light or closest ultraviolet light range (i.e., in the wavelength range of 380 nm to 800 nm) and a full width at half maximum of less than 0.60 eV (preferably less than 0.50 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even less than 0.40 eV) in a film of poly(methyl methacrylate) (PMMA) using 10 wt% of the organic molecules at room temperature.

[0242] Orbital and excited state energies can be determined experimentally or by calculation using quantum chemical methods (specifically, density functional theory calculations). The energy of the highest occupied molecular orbital (E HOMO ) is determined by methods known to those skilled in the art via cyclic voltammetry measurements with an accuracy of 0.1 eV. The energy of the lowest unoccupied molecular orbital (E LUMO ) was determined as the onset of the absorption spectrum.

[0243] The absorption spectra of the organic molecules according to the invention are usually recorded at room temperature (i.e. approximately 20° C.) through films of the organic molecules according to the invention in poly(methyl methacrylate) (PMMA) using 10% by weight of the organic molecules. Alternatively, they can also be recorded through solutions of the corresponding molecules, wherein the concentration of the solution is selected such that the maximum absorbance is preferably in the range of 0.1 to 0.5.

[0244] The starting point of the absorption spectrum is determined by calculating the intersection of the tangent line of the absorption spectrum with the x-axis. The tangent line of the absorption spectrum is set at the low energy side of the absorption band and at the half maximum point of the maximum intensity of the absorption spectrum.

[0245] Unless stated otherwise, the energy of the first excited triplet state (T1) was determined via the onset of the phosphorescence spectrum at 77 K (steady-state spectrum; film of 10 wt. % emitter in PMMA).

[0246] Unless otherwise stated, the energy of the first excited singlet state (S1) was determined from the onset of the fluorescence spectrum at room temperature (ie, approximately 20° C.; steady-state spectrum; film of 10 wt % emitter in PMMA).

[0247] The starting point of the emission spectrum is determined by calculating the intersection of the tangent line of the emission spectrum with the x-axis. The tangent line of the emission spectrum is set at the high energy side of the emission band and at the point of half maximum of the maximum intensity of the emission spectrum.

[0248] ΔE corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) ST The value is determined based on the first excited singlet energy and the first excited triplet energy determined as described above.

[0249] A further aspect of the invention relates to the use of the organic molecules according to the invention as luminescent emitters or as absorbers and / or as host materials and / or as electron transport materials and / or as hole injection materials and / or as hole blocking materials in optoelectronic devices.

[0250] An optoelectronic device may be understood in the broadest sense as any device based on an organic material suitable for emitting light in the visible or proximal ultraviolet (UV) range (i.e., in the wavelength range of 380 nm to 800 nm). More preferably, the optoelectronic device may be capable of emitting light in the visible range (i.e., 400 nm to 800 nm).

[0251] In the context of this application, the optoelectronic device is more particularly selected from the group consisting of:

[0252] Organic light-emitting diodes (OLEDs);

[0253] Light-emitting electrochemical cells;

[0254] OLED sensors, in particular, gas and vapor sensors that are not hermetically isolated from the outside;

[0255] Organic diodes;

[0256] Organic solar cells;

[0257] Organic transistors;

[0258] Organic field-effect transistors;

[0259] organic lasers; and

[0260] Down-conversion components.

[0261] The light-emitting electrochemical cell consists of three layers, namely a cathode, an anode and an active layer comprising the organic molecules according to the invention.

[0262] In a preferred embodiment in the context of this application, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic laser and a light emitting transistor.

[0263] In one embodiment, the light-emitting layer (or "emission layer") of an organic light-emitting diode includes not only the organic molecule according to the invention, but also a host material whose triplet (T1) energy level and singlet (S1) energy level are energetically higher than the triplet (T1) energy level and singlet (S1) energy level of the organic molecule.

[0264] Another aspect of the invention relates to a composition comprising or consisting of the following ingredients:

[0265] (a) the inventive organic molecules, in particular in the form of emitters and / or hosts; and

[0266] (b) one or more emitter and / or host materials different from the inventive organic molecules; and

[0267] (c) optionally, one or more dyes and / or one or more solvents.

[0268] In yet another embodiment of the invention, the composition has a photoluminescence quantum yield (PLQY) greater than 26% (preferably greater than 40%, more preferably greater than 60%, even more preferably greater than 80%, or even greater than 90%) at room temperature.

[0269] Composition with at least one other emitter

[0270] One embodiment of the invention relates to a composition comprising or consisting of the following ingredients:

[0271] (i) 1 to 50 wt. % (preferably 5 to 40 wt. %, in particular 10 to 30 wt. %) of an organic molecule according to the invention (E);

[0272] (ii) 5 to 98 wt% (preferably 30 to 93.9 wt%, specifically 40 to 88 wt%) of a host compound (H);

[0273] (iii) 1 to 30% by weight, in particular 1 to 20% by weight, preferably 1 to 5% by weight, of at least one further emitter molecule (F) having a structure that differs from the structure of the organic molecule (E) according to the invention; and

[0274] (iv) optionally, 0 to 94 wt. % (preferably 0.1 to 65 wt. %, in particular 1 to 50 wt. %) of at least one further host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0275] (v) Optionally, 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight) of a solvent.

[0276] The ingredients or components are selected so that the sum of the weights of the ingredients adds up to 100%.

[0277] In yet another embodiment of the invention, the composition has an emission peak in the visible light or closest ultraviolet light range (ie, in the wavelength range of 380 nm to 800 nm).

[0278] In one embodiment of the invention, the at least one further emitter molecule (F) is a purely organic emitter.

[0279] In one embodiment of the invention, at least one further emitter molecule (F) is a pure organic TADF emitter. Pure organic TADF emitters are known from the prior art, for example, Wong and Zysman-Colman ("Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light-Emitting Diodes.", Adv. Mater. 2017 Jun; 29(22)).

[0280] In one embodiment of the invention, the at least one further emitter molecule (F) is a fluorescent emitter (in particular a blue, green or red fluorescent emitter).

[0281] In a further embodiment of the invention, the composition comprising at least one further emitter molecule (F) exhibits an emission peak in the visible or very close to ultraviolet range (i.e. in the wavelength range of 380 nm to 800 nm) at room temperature and a full width at half maximum of less than 0.30 eV (in particular less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.19 eV, or even less than 0.17 eV) and a lower limit of 0.05 eV.

[0282] Emitting Layer (EML)

[0283] In one embodiment, the light emitting layer (EML) of the inventive organic light emitting diode comprises (or consists essentially of) a composition comprising or consisting of the following components:

[0284] (i) 1 to 50 wt. % (preferably 5 to 40 wt. %, in particular 10 to 30 wt. %) of one or more organic molecules according to the invention (E);

[0285] (ii) 5 to 99 wt% (preferably 30 to 94.9 wt%, specifically 40 to 89 wt%) of at least one host compound (H); and

[0286] (iii) optionally, 0 to 94 wt. % (preferably 0.1 to 65 wt. %, in particular 1 to 50 wt. %) of at least one further host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0287] (iv) optionally, 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight) of a solvent; and

[0288] (v) optionally, 0% to 30% by weight (in particular 0% to 20% by weight, preferably 0% to 5% by weight) of at least one further emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention.

[0289] Preferably, energy can be transferred from the host compound (H) to one or more of the inventive organic molecules (E), specifically, energy can be transferred from the first excited triplet state (T1(H)) of the host compound (H) to the first excited triplet state (T1(E)) of one or more of the inventive organic molecules (E), and / or from the first excited singlet state (S1(H)) of the host compound (H) to the first excited singlet state (S1(E)) of one or more of the inventive organic molecules (E).

[0290] In one embodiment, the host compound (H) has an energy (E HOMO (H)), an organic molecule (E) according to the invention has an energy (E HOMO (E)) highest occupied molecular orbital (HOMO(E)), where E HOMO (H)>E HOMO (E).

[0291] In another embodiment, the host compound (H) has an energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), an organic molecule (E) according to the invention has an energy (E LUMO (E)) of the lowest unoccupied molecular orbital (LUMO(E)), where E LUMO (H)>E LUMO (E).

[0292] an emitting layer (EML) comprising at least one other host compound (D)

[0293] In yet another embodiment, the light emitting layer (EML) of the organic light emitting diode of the present invention comprises (or consists essentially of) a composition comprising or consisting of the following components:

[0294] (i) 1 to 50 wt. % (preferably 5 to 40 wt. %, in particular 10 to 30 wt. %) of one organic molecule (E) according to the invention;

[0295] (ii) 5 to 99 wt% (preferably 30 to 94.9 wt%, specifically 40 to 89 wt%) of a host compound (H); and

[0296] (iii) 0 to 94 wt. % (preferably 0.1 to 65 wt. %, in particular 1 to 50 wt. %) of at least one further host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0297] (iv) optionally, 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight) of a solvent; and

[0298] (v) optionally, 0% to 30% by weight (in particular 0% to 20% by weight, preferably 0% to 5% by weight) of at least one further emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention.

[0299] In one embodiment of the organic light emitting diode of the invention, the host compound (H) has an energy (E HOMO (H)), at least one other host compound (D) has an energy (E HOMO (D))'s highest occupied molecular orbital (HOMO(D)), where E HOMO (H)>E HOMO(D). Relationship E HOMO (H)>E HOMO (D) It is conducive to efficient hole transport.

[0300] In another embodiment, the host compound (H) has an energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), at least one other host compound (D) has an energy (E LUMO (D)) of the lowest unoccupied molecular orbital (LUMO(D)), where E LUMO (H)>E LUMO (D). Relationship E LUMO (H)>E LUMO (D) Facilitates efficient electron transport.

[0301] In one embodiment of the organic light emitting diode of the invention, the host compound (H) has an energy (E HOMO (H))'s highest occupied molecular orbital (HOMO(H)) and possessing energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), and

[0302] At least one other host compound (D) has an energy (E HOMO (D))'s highest occupied molecular orbital (HOMO(D)) and possessing energy (E LUMO (D))'s lowest unoccupied molecular orbital (LUMO(D)),

[0303] The invented organic molecule (E) has energy (E HOMO (E))'s highest occupied molecular orbital (HOMO(E)) and possessing energy (E LUMO (E))'s lowest unoccupied molecular orbital (LUMO(E)),

[0304] in,

[0305] E HOMO (H)>E HOMO (D), and according to the energy level (E) of the highest occupied molecular orbital (HOMO(E)) of the organic molecule (E) of the invention HOMO (E)) and the energy level (E) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) HOMO (H)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0306] E LUMO (H)>ELUMO (D), and according to the energy level (E) of the lowest unoccupied molecular orbital (LUMO(E)) of the inventive organic molecule (E) LUMO (E)) and the energy level (E) of the lowest unoccupied molecular orbital (LUMO (D)) of at least one other host compound (D) LUMO (D)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0307] a light-emitting layer (EML) comprising at least one further emitter molecule (F)

[0308] In yet another embodiment, the emissive layer (EML) comprises (or consists (essentially) of) a composition comprising or consisting of:

[0309] (i) 1 to 50 wt. % (preferably 5 to 40 wt. %, in particular 10 to 30 wt. %) of one organic molecule (E) according to the invention;

[0310] (ii) 5 to 98 wt% (preferably 30 to 93.9 wt%, specifically 40 to 88 wt%) of a host compound (H);

[0311] (iii) 1 to 30% by weight, in particular 1 to 20% by weight, preferably 1 to 5% by weight, of at least one further emitter molecule (F) having a structure that differs from the structure of the organic molecule (E) according to the invention; and

[0312] (iv) optionally, 0 to 94 wt. % (preferably 0.1 to 65 wt. %, in particular 1 to 50 wt. %) of at least one further host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0313] (v) Optionally, 0% to 94% by weight (preferably, 0% to 65% by weight, specifically, 0% to 50% by weight) of a solvent.

[0314] In yet another embodiment, the light emitting layer (EML) comprises (or (essentially consists of) a composition as described for the composition having at least one further emitter and at least one further emitter molecule (F) as defined in the composition wherein the at least one further emitter molecule (F) is a blue fluorescent emitter.

[0315] In yet another embodiment, the light emitting layer (EML) comprises (or (essentially consists of) a composition as described for the composition having at least one further emitter and at least one further emitter molecule (F) as defined in the composition wherein the at least one further emitter molecule (F) is a triplet-triplet annihilation (TTA) fluorescence emitter.

[0316] In yet another embodiment, the light emitting layer (EML) comprises (or (essentially consists of) a composition as described for the composition having at least one further emitter and at least one further emitter molecule (F) as defined for the composition wherein the at least one further emitter molecule (F) is a green fluorescent emitter.

[0317] In yet another embodiment, the light emitting layer (EML) comprises (or (essentially consists of) a composition as described for the composition having at least one further emitter and at least one further emitter molecule (F) as defined in the composition wherein the at least one further emitter molecule (F) is a red fluorescent emitter.

[0318] In one embodiment of the light-emitting layer (EML) comprising at least one further emitter molecule (F), energy can be transferred from the one or more inventive organic molecules (E) to the at least one further emitter molecule (F), in particular, energy can be transferred from the first excited singlet state (S1(E)) of the one or more inventive organic molecules (E) to the first excited singlet state (S1(F)) of the at least one further emitter molecule (F).

[0319] In one embodiment, the first excited singlet state (S1(H)) of one host compound (H) of the light-emitting layer is higher in energy than the first excited singlet state (S1(E)) of one or more inventive organic molecules (E): S1(H)>S1(E), and the first excited singlet state (S1(H)) of one host compound (H) is higher in energy than the first excited singlet state (S1(F)) of at least one emitter molecule (F): S1(H)>S1(F).

[0320] In one embodiment, the first excited triplet state (T1(H)) of one host compound (H) is higher in energy than the first excited triplet state (T1(E)) of one or more inventive organic molecules (E): T1(H)>T1(E), and the first excited triplet state (T1(H)) of one host compound (H) is higher in energy than the first excited triplet state (T1(F)) of at least one emitter molecule (F): T1(H)>T1(F).

[0321] In one embodiment, the first excited singlet state (S1(E)) of the one or more inventive organic molecules (E) is higher in energy than the first excited singlet state (S1(F)) of the at least one emitter molecule (F): S1(E)>S1(F).

[0322] In one embodiment, the first excited triplet state (T1(E)) of the one or more inventive organic molecules (E) is higher in energy than the first excited singlet state (T1(F)) of the at least one emitter molecule (F): T1(E)>T1(F).

[0323] In one embodiment, the first excited triplet state (T1(E)) of the one or more inventive organic molecules (E) is higher in energy than the first excited singlet state (T1(F)) of the at least one emitter molecule (F): T1(E)>T1(F), wherein the absolute value of the energy difference between T1(E) and T1(F) is greater than 0.3 eV (preferably greater than 0.4 eV, or even greater than 0.5 eV).

[0324] In one embodiment, the host compound (H) has an energy (E HOMO (H))'s highest occupied molecular orbital (HOMO(H)) and possessing energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), and

[0325] An organic molecule (E) according to the invention has an energy (E HOMO (E))'s highest occupied molecular orbital (HOMO(E)) and possessing energy (E LUMO(E))'s lowest unoccupied molecular orbital (LUMO(E)),

[0326] At least one further emitter molecule (F) has an energy (E HOMO (F)) and the highest occupied molecular orbital (HOMO(F)) and the energy (E LUMO (F))'s lowest unoccupied molecular orbital (LUMO(F)),

[0327] in,

[0328] E HOMO (H)>E HOMO (E), and the energy level (E) of the highest occupied molecular orbital (HOMO(F)) of at least one other emitter molecule (F) HOMO (F)) and the energy level (E) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) HOMO (H)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0329] E LUMO (H)>E LUMO (E), and the energy level (E) of the lowest unoccupied molecular orbital (LUMO(F)) of at least one other emitter molecule (F) LUMO (F)) and the energy level (E) of the lowest unoccupied molecular orbital (LUMO(E)) of an organic molecule (E) according to the invention LUMO (E)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0330] Optoelectronic devices

[0331] In yet another aspect, the invention relates to an optoelectronic device comprising an organic molecule or composition as described herein, more particularly, the optoelectronic device is in the form of a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell, an OLED sensor (particularly, a gas and vapor sensor that is not externally sealed and isolated), an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a down-conversion element.

[0332] In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light emitting transistor.

[0333] In one embodiment of the inventive optoelectronic device, the organic molecules according to the invention are used as emissive material in the light emitting layer (EML).

[0334] In one embodiment of the inventive optoelectronic device, the light-emitting layer (EML) consists of the composition according to the invention as described herein.

[0335] When the optoelectronic device is an OLED, it may, for example, exhibit the following layer structure:

[0336] 1. Base

[0337] 2. Anode layer, A

[0338] 3. Hole injection layer, HIL

[0339] 4. Hole transport layer, HTL

[0340] 5. Electron blocking layer, EBL

[0341] 6. Emission Layer, EML

[0342] 7. Hole blocking layer, HBL

[0343] 8. Electron Transport Layer, ETL

[0344] 9. Electron injection layer, EIL

[0345] 10. Cathode layer, C,

[0346] Where the OLED comprises each layer, only optionally different layers may be combined, the OLED may comprise more than one layer of each layer type defined above.

[0347] Additionally, optoelectronic devices may optionally include one or more protective layers that protect the device from damage due to exposure to harmful substances in the environment, including, for example, moisture, steam, and / or gases.

[0348] In one embodiment of the invention, the optoelectronic device is an OLED exhibiting the following inverted layer structure:

[0349] 1. Base

[0350] 2. Cathode layer, C

[0351] 3. Electron injection layer, EIL

[0352] 4. Electron Transport Layer, ETL

[0353] 5. Hole blocking layer, HBL

[0354] 6. Emission Layer, EML

[0355] 7. Electron blocking layer, EBL

[0356] 8. Hole transport layer, HTL

[0357] 9. Hole injection layer, HIL

[0358] 10. Anode layer, A,

[0359] Wherein an OLED having an inverted layer structure comprises each layer, only optionally different layers may be combined, the OLED may comprise more than one layer of each layer type defined above.

[0360] In one embodiment of the invention, the optoelectronic device is an OLED that can exhibit a stacked structure. In this structure, the individual units are stacked on top of each other, as opposed to the typical arrangement in which OLEDs are placed side by side. OLEDs that exhibit a stacked structure can produce mixed light, specifically, white light can be produced by stacking a blue OLED, a green OLED, and a red OLED. In addition, an OLED that exhibits a stacked structure can optionally include a charge generation layer (CGL), which is typically positioned between two OLED subunits and typically consists of an n-doped layer and a p-doped layer, with the n-doped layer of one CGL typically positioned close to the anode layer.

[0361] In one embodiment of the invention, the optoelectronic device is an OLED comprising two or more emissive layers between an anode and a cathode. Specifically, this so-called tandem OLED comprises three emissive layers, wherein one emissive layer emits red light, one emissive layer emits green light, and one emissive layer emits blue light, and optionally other layers such as charge generation layers, blocking layers, or transport layers may be included between the emissive layers. In another embodiment, the emissive layers are stacked adjacent to each other. In another embodiment, the tandem OLED comprises a charge generation layer between each two emissive layers. Additionally, adjacent emissive layers or emissive layers separated by a charge generation layer may be combined.

[0362] The substrate can be formed of any material or combination of materials. Most commonly, a glass slide is used as a substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver or aluminum film) or a plastic film or slide can be used. This can allow a higher degree of flexibility. The anode layer (A) is mainly composed of a material that allows a (substantially) transparent film to be obtained. Since at least one of the two electrodes should be (substantially) transparent to allow light to be emitted from the OLED, the anode layer (A) or the cathode layer (C) is transparent. Preferably, the anode layer (A) includes a large amount of transparent conductive oxide (TCO), or even consists of a transparent conductive oxide (TCO). Such an anode layer (A) can, for example, include indium tin oxide, aluminum zinc oxide, fluorine-doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene.

[0363] Preferably, the anode layer (A) consists (essentially) of indium tin oxide (ITO) (e.g. (InO3) 0.9 (SnO2) 0.1). The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). In addition, because the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is promoted, the HIL can promote the injection of quasi-charge carriers (i.e., holes). The hole injection layer (HIL) may include poly (3,4-ethylenedioxythiophene) (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC or CuI (specifically, a mixture of PEDOT and PSS). The hole injection layer (HIL) can also prevent the diffusion of metal from the anode layer (A) into the hole transport layer (HTL). The HIL may include PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrenesulfonate), PEDOT (poly(3,4-ethylenedioxythiophene)), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylphenyl-1,4-diamine)), NPB (N ,N'-bis(1-naphthyl)-N,N'-bis-phenyl(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0364] Adjacent to the anode layer (A) or the hole injection layer (HIL), a hole transport layer (HTL) is typically positioned. Any hole transport compound can be used herein. Exemplarily, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer (A) and the light-emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high energy level of its triplet state (T1). For example, the hole transport layer (HTL) may include tris(4-carbazol-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), α-NPD (N,N′-bis(naphthalene-1-yl)-N,N′-bis(phenyl)-2,2′-dimethylbenzidine), TAPC (4,4′-cyclohexyl-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, Me Star-shaped heterocycles of O-TPD, HAT-CN, and / or Tris-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, the HTL may include a p-doped layer that may be composed of an inorganic dopant or an organic dopant in an organic hole-transporting matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide may be used as inorganic dopants. Tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes may be used as organic dopants.

[0365] The EBL may include mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazol-9-yl)biphenyl), Tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N′-dicarbazyl-1,4-dimethylbenzene).

[0366] Adjacent to the hole transport layer (HTL), an emissive layer (EML) is typically positioned. The emissive layer (EML) includes at least one organic molecule. Specifically, the EML includes at least one organic molecule according to the invention. Typically, the EML additionally includes one or more host materials. Exemplarily, the host material is selected from CBP (4,4'-bis(N-carbazolyl)biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, The host material may be selected to exhibit a first triplet state (T1) energy level and a first singlet state (S1) energy level that are energetically higher than the first triplet state (T1) energy level and the first singlet state (S1) energy level of the organic molecule.

[0367] In one embodiment of the invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one organic molecule according to the invention and a hybrid host system comprising T2T as an electron-dominant host and a host selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophen-2-yl)phenyl]-9H-carbazole as a hole-dominant host. In another embodiment, the EML includes 50 wt % to 80 wt % (preferably 60 wt % to 75 wt %) of a host, 10 wt % to 45 wt % (preferably 15 wt % to 30 wt %) of T2T, and 5 wt % to 40 wt % (preferably 10 wt % to 30 wt %) of an organic molecule according to the invention, wherein the host is selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole.

[0368] Adjacent to the light-emitting layer (EML), an electron transport layer (ETL) may be positioned. Any electron transporter may be used. For example, electron-poor compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). The ETL may include NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2′-bipyridin-5-yl)triphenylene), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yldiphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), and / or BTB (4,4′-bis[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl). Optionally, the ETL may be doped with a material such as Liq. An electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0369] HBL may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), BAlq (bis(8-hydroxy-2-methylquinolinol)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinolinol)aluminum), TSPO1 (diphenyl-4-triphenylsilyl) phenyl-phosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(terphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene).

[0370] The cathode layer (C) can be positioned adjacent to the electron transport layer (ETL). For example, the cathode layer (C) can include a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or can be composed of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer can also be composed of a (substantially) opaque metal such as Mg, Ca, or Al. Alternatively or additionally, the cathode layer (C) can also include graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer (C) can also be composed of nanoscale silver wires.

[0371] The OLED may further optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (8-hydroxyquinoline lithium), Li2O, BaF2, MgO and / or NaF.

[0372] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may also include one or more host compounds.

[0373] In order to further modify the emission spectrum and / or absorption spectrum of the light-emitting layer (EML), the light-emitting layer (EML) may further include one or more other emitter molecules (F). Such emitter molecules (F) may be any emitter molecules known in the art. Preferably, such emitter molecules (F) are molecules having a structure different from that of the organic molecules according to the invention. The emitter molecule (F) may alternatively be a TADF emitter. Alternatively, the emitter molecule (F) may alternatively be a fluorescent and / or phosphorescent emitter molecule capable of shifting the emission spectrum and / or absorption spectrum of the light-emitting layer (EML). For example, by emitting light that is typically red-shifted compared to the light emitted by the organic molecule (E), triplet and / or singlet excitons may be transferred from the organic molecule (E) according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Alternatively, the emitter molecule (F) may also cause a two-photon effect (i.e., absorption of half the energy of the absorption maximum by two photons).

[0374] Alternatively, the optoelectronic device (e.g., an OLED) can be, for example, a substantially white optoelectronic device. For example, such a white optoelectronic device can include at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Energy transfer can optionally occur between the two or more molecules described above.

[0375] As used herein, if not more specifically defined in a particular context, the color of emitted and / or absorbed light is designated as follows:

[0376] Purple: wavelength range of >380nm to 420nm;

[0377] Dark blue: wavelength range of >420nm to 480nm;

[0378] Sky blue: wavelength range of >480nm to 500nm;

[0379] Green: >500nm to 560nm wavelength range;

[0380] Yellow: >560nm to 580nm wavelength range;

[0381] Orange: >580nm to 620nm wavelength range;

[0382] Red: >620nm to 800nm ​​wavelength range.

[0383] For emitter molecules, this color refers to the emission maximum. Thus, for example, a deep blue emitter has an emission maximum in the range of >420 nm to 480 nm, a sky blue emitter has an emission maximum in the range of >480 nm to 500 nm, a green emitter has an emission maximum in the range of >500 nm to 560 nm, and a red emitter has an emission maximum in the range of >620 nm to 800 nm.

[0384] Yet another aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to CIEx (=0.131) and CIEy (=0.046) color coordinates, which are the primary color blue (CIEx=0.131, CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and is therefore suitable for use in ultra-high-definition (UHD) displays (e.g., UHD-TV). Therefore, a further aspect of the invention relates to an OLED, the emission of which exhibits CIEx color coordinates between 0.02 and 0.30 (preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20, or even more preferably between 0.08 and 0.18, or even between 0.10 and 0.15) and / or CIEy color coordinates between 0.00 and 0.45 (preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20, or even more preferably between 0.03 and 0.15, or even between 0.04 and 0.10).

[0385] Yet another embodiment of the present invention relates to an OLED that emits light having CIEx (=0.170) and CIEy (=0.797) color coordinates that are close to the CIEx (=0.170) and CIEy (=0.797) color coordinates, which are the primary color green (CIEx=0.170, CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and the OLED is therefore suitable for use in ultra-high-definition (UHD) displays (e.g., UHD-TV). In this context, the term "close" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting (top electrode is transparent) devices are typically used, while the test devices as used throughout this application represent bottom-emitting devices (bottom electrode and substrate are transparent). Therefore, a further aspect of the invention relates to an OLED, the emission of which exhibits CIEx color coordinates between 0.15 and 0.45 (preferably between 0.15 and 0.35, more preferably between 0.15 and 0.30, or even more preferably between 0.15 and 0.25, or even between 0.15 and 0.20) and / or CIEy color coordinates between 0.60 and 0.92 (preferably between 0.65 and 0.90, more preferably between 0.70 and 0.88, or even more preferably between 0.75 and 0.86, or even between 0.79 and 0.84).

[0386] Another aspect of the present invention relates to an OLED having a brightness of 14500 cd / m 2 and / or an emission maximum between 500 nm and 560 nm (more preferably between 510 nm and 550 nm, even more preferably between 520 nm and 540 nm), and / or an external quantum efficiency of greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 17%, or even greater than 20%) at a wavelength of 14500 nm and / or an emission maximum between 14500 cd / m 2 The present invention preferably exhibits an LT97 value of greater than 100 hours (preferably greater than 250 hours, more preferably greater than 500 hours, even more preferably greater than 750 hours, or even greater than 1000 hours) under the conditions described above.

[0387] Another aspect of the present invention relates to an OLED having a brightness of 1000 cd / m 2and / or an emission maximum between 420 nm and 500 nm (more preferably between 430 nm and 490 nm, even more preferably between 440 nm and 480 nm), and / or an external quantum efficiency of greater than 8% (more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even greater than 20%) at a wavelength of 500 nm or less. 2 The invention further comprises a LT80 value of greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even greater than 1000 hours) under the conditions described above.

[0388] Yet another aspect of the present invention relates to an OLED that emits light at different color points. According to the present invention, the OLED emits light having a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the invention emits light having a main emission peak FWHM of less than 0.50 eV (preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even less than 0.40 eV).

[0389] In yet another aspect, the invention relates to a method for producing an optoelectronic device, in which case the inventive organic molecule is used.

[0390] The optoelectronic device (in particular, OLED) according to the present invention can be manufactured by any means of vapor deposition and / or liquid processing. Thus, at least one layer:

[0391] -Prepared by sublimation process,

[0392] -Prepared by organic vapor deposition process,

[0393] -Prepared by carrier gas sublimation process,

[0394] -Solution processed or printed.

[0395] The method for manufacturing an optoelectronic device (in particular, an OLED) according to the present invention is known in the art. Different layers are deposited individually and successively on a suitable substrate by means of subsequent deposition processes. The same or different deposition methods can be used to deposit each layer.

[0396] Vapor deposition processes can include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as a substrate. Each layer can be processed from a solution or dispersion using an appropriate solvent. Solution deposition processes illustratively include spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent can be completely or partially removed by methods known in the art.

[0397] Example

[0398] General Synthesis Scheme I

[0399] Illustratively, General Synthesis Scheme I provides a synthesis scheme for an organic molecule M1 according to the invention, wherein the first chemical moiety has a structure according to Formula Ia, wherein T is the binding site of a single bond connecting the first chemical moiety to the second chemical moiety and wherein X is R X :

[0400]

[0401] Where E3 and E4 are identical, two nucleophilic substitution reactions can be carried out in a single synthesis step (in other words: M1 is obtained directly via P1). For this purpose, reactant E3=E4 is used in a threefold excess as will be described in the synthesis step (step 4).

[0402] General Synthetic Scheme II

[0403] Illustratively, General Synthesis Scheme II provides a synthesis scheme for an organic molecule M2 according to the invention, wherein the first chemical moiety has a structure according to Formula Ib, wherein T is the binding site of a single bond connecting the first chemical moiety to the second chemical moiety and wherein X is R X :

[0404]

[0405] Unlike general synthesis scheme I, general synthesis scheme II exemplarily shows a two-step synthesis of compound M2, which is made possible by the fact that all donor parts (reactants: E7, used in excess) in M2 are exemplarily selected to be the same. As can be seen in general synthesis scheme I, this is not a prerequisite. More details can be obtained through experimental steps.

[0406] General Synthetic Scheme III

[0407] Illustratively, General Synthesis Scheme III provides a synthesis scheme for an organic molecule M3 according to the invention, wherein the first chemical moiety has a structure according to Formula Ia, wherein W is the binding site of a single bond connecting the first chemical moiety to the second chemical moiety and wherein X is R X :

[0408]

[0409] General Synthetic Scheme IV

[0410] Illustratively, General Synthesis Scheme IV provides a synthesis scheme for organic molecule M4 according to the invention, wherein the first chemical moiety has a structure according to Formula Ib, wherein W is the binding site of a single bond connecting the first chemical moiety to the second chemical moiety and wherein X is R X :

[0411]

[0412] Synthesis of E1

[0413]

[0414] General Synthetic Scheme V

[0415]

[0416] General Synthetic Scheme VI

[0417]

[0418] General Synthetic Scheme VII

[0419]

[0420] General steps for synthesis:

[0421] Steps for Synthesis Scheme I

[0422] Step 1

[0423] Under a nitrogen atmosphere, a mixture of THF and water (4: 1 volume ratio) was added to boronic acid pinacol ester E2 (1.00 equivalents), 2,4-dichloro-1,3,5-triazine derivatives (1.50 equivalents), potassium carbonate (2.00 equivalents) and tetrakis(triphenylphosphine)palladium(0) (0.03 equivalents, CAS 14221-01-3), followed by nitrogen bubbling for 10 minutes. The reaction mixture was stirred at 60°C until complete conversion of boronic acid pinacol ester E2 was reached as judged by GC / MS and TLC. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and brine. The organic extract was concentrated under reduced pressure. The crude product was purified by column chromatography to obtain P1 as a solid.

[0424] Step 2

[0425] P1 (1.20 equivalents, product of step 1), E3 (1.00 equivalents) and tripotassium phosphate (2.00 equivalents) were suspended in anhydrous DMSO under a nitrogen atmosphere and stirred at 90° C. for 2 hours (reaction monitored via GC / MS and TLC). Subsequently, the reaction mixture was poured into a stirred mixture of water and ice. The resulting precipitate was filtered off and washed with water and ethanol. The crude product was purified by additional washing with dichloromethane to obtain P2 as a solid.

[0426] Step 3

[0427] Under nitrogen atmosphere, anhydrous THF is added P2 (1.00 equivalents, the product of step 2) and E4 (1.30 equivalents), and then sodium hydride (1.30 equivalents) is added. Once H2 emission has stopped, the reaction mixture is heated to 60°C under stirring. After the reaction is completed based on the reaction monitored by LC / MS and TLC, the reaction is carefully poured into water. The gained precipitate is filtered out and then washed with water, ethanol and hexane. The crude product is purified by column chromatography and subjected to heat washing with toluene to obtain M1 as a solid. Alternatively, the reaction mixture quenched with ethyl acetate and salt water extraction can be used. The organic layer combined is then dried with anhydrous MgSO4, the solvent is removed under reduced pressure, and the residue is recrystallized by ethyl acetate. In dichloromethane, the gained crude product is heated to reflux for 2 hours, then hot filtered and washed with ethanol solid, to obtain M1 as a solid.

[0428] Step 4, double nucleophilic substitution reaction (P1→M1)

[0429] This step is similar to step 3 above except that P1 (1.00 equiv) is used instead of P2 along with 3.00 equiv of donor molecule E3=E4 and 3.00 equiv of sodium hydride.

[0430] Steps for Synthesis Scheme II

[0431] Step 5

[0432] Under nitrogen atmosphere, E6 (1.00 equivalents) is dissolved in anhydrous THF, and then nitrogen is bubbled for 10 minutes. After being cooled to -20 ℃, isopropylmagnesium chloride-lithium chloride complex (1.10 equivalents, CAS:745038-86-2) is added, then stirred at the same temperature for 1 hour. Using cannula, cold Grignard solution (Grignard solution) is slowly transferred to a solution of cyanuric chloride (E5, 1.10 equivalents, CAS:108-77-0) in anhydrous THF (nitrogen atmosphere, room temperature). The reaction mixture is heated to 60 ℃ and stirred for 1.5 hours (reaction is monitored via GC / MS and TLC), and after being cooled to room temperature, quenched by adding water. Extracted with dichloromethane, the organic layer combined is then treated with charcoal, filtered, and the solvent is removed under reduced pressure. Purification of crude product is carried out by column chromatography using cyclohexane / dichloromethane as eluent to obtain product P3 as a solid.

[0433] Step 6

[0434] This step is similar to step 4 except using P3 (1.00 eq.) instead of P1 and E7 (4.00 eq.) as reactants along with 4.00 eq. of sodium hydride. The product M2 is obtained as a solid.

[0435] Steps for the synthesis of Scheme III

[0436] Step 7

[0437] Under a nitrogen atmosphere, E3 (1.00 equivalents) was dissolved in THF. At 0°C, n-butyl lithium (1.0 equivalents, 2.5M in hexane) was added dropwise and then stirred at room temperature for 20 minutes. In a separate flask, E1 (1.50 equivalents) was dissolved in THF under a nitrogen atmosphere. To this solution, a pre-prepared lithium substance was added dropwise. Subsequently, the mixture was heated under reflux until complete conversion of E1 was achieved as judged by GC / MS and TLC. After cooling to room temperature, water was added, the precipitated solid was filtered out, and it was washed with water and ethanol to obtain P4 as a solid. The substance can be further purified by recrystallization.

[0438] Step 8

[0439] Under a nitrogen atmosphere, a mixture of toluene and water was added to boric acid E8 (1.20 equivalents), P4 (1.00 equivalents, the product of step 7), potassium carbonate (2.00 equivalents) and [1,1'-bis(diphenylphosphino)ferrocene] palladium (II) dichloride (0.05 equivalents, CAS 72287-26-4). The reaction mixture was stirred at reflux until complete conversion of P4 was achieved as determined by GC / MS and TLC. After cooling to room temperature, water was added and then extracted with dichloromethane and water. The combined organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was heated to reflux for 2 hours in ethanol and washed with ethanol during hot filtration. The hot filtration step was then repeated with a 1:1 mixture of methanol and water to obtain product P5 as a solid.

[0440] Step 9

[0441] The procedure was similar to step 2 except that P5 (1.00 eq., product of step 8) was used instead of P1 and E4 (1.10 eq.) was used instead of E3 along with 2.20 eq. of tripotassium phosphate. M3 was obtained as a solid.

[0442] Steps for Synthesis Scheme IV

[0443] Step 10

[0444] Under a nitrogen atmosphere, E3 (2.00 equivalents) was dissolved in THF. At 0°C, n-butyl lithium (2.10 equivalents, 2.5M in hexane) was added dropwise and then stirred at room temperature for 20 minutes. In a separate flask, E5 (1.00 equivalents) was dissolved in THF under a nitrogen atmosphere. To this solution, a pre-prepared lithium substance was added dropwise. The mixture was then heated under reflux until complete conversion of E5 was achieved as judged by GC / MS and TLC. After cooling to room temperature, water was added, the precipitated solid was filtered out, and it was washed with water and ethanol to obtain P6 as a solid. The substance can be further purified by recrystallization.

[0445] Step 11

[0446] Except using P6 (1.00 equivalent, the product of step 10) instead of P4, this step is similar to step 8. After the reaction is judged to be complete by GC / MS and TLC, the reaction mixture is cooled to room temperature, poured into water, and the resulting precipitate is filtered out. It is washed with water and ethyl acetate to obtain P7 as a solid.

[0447] Step 12

[0448] The procedure was similar to step 2 except that P7 (1.00 equiv., product of step 11) was used instead of P1 and E4 (1.10 equiv.) was used instead of E3 along with 2.20 equiv. of tripotassium phosphate. M4 was obtained as a solid.

[0449] Steps for the synthesis of E1

[0450] Step 13

[0451] Under a nitrogen atmosphere, E1aa (1.00 equivalents, CAS: 2052-07-5) was dissolved in anhydrous THF, and then nitrogen was bubbled for 10 minutes. The solution was added dropwise to activated magnesium (3.00 equivalents, CAS: 7439-95-4) in anhydrous THF, and then stirred for 2h at the same temperature. Using a cannula, the cold Grignard solution was slowly transferred to a solution of cyanuric chloride (E5, 1.50 equivalents, CAS: 108-77-0) in anhydrous toluene (nitrogen atmosphere, room temperature). The reaction mixture was heated to 78 ° C and stirred for 8 hours (reaction monitored via GC / MS and TLC), and after cooling to room temperature, quenched by adding water. It was extracted with dichloromethane, then the combined organic layer was treated with charcoal, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using cyclohexane / dichloromethane as eluent to obtain the product E1 as a solid.

[0452] Steps for the Synthesis of Scheme V

[0453] Step 13a

[0454] Under nitrogen atmosphere, a mixture of toluene and water (7: 1 volume ratio) was added to boronic acid E7aa (1.00 equivalent), E6aa (1.50 equivalents), potassium carbonate (2.00 equivalents) and tetrakis (triphenylphosphine) palladium (0) (0.03 equivalent, CAS 14221-01-3), followed by nitrogen bubbling for 10 minutes. The reaction mixture was stirred at 60°C until the complete conversion of boronic acid E7aa was determined by GC / MS and TLC. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate and saline. The organic extract was concentrated under reduced pressure. The crude product was purified by column chromatography to obtain P4 as a solid.

[0455] Step 14

[0456] Under a nitrogen atmosphere, a mixture of dioxane and water (10:1 volume ratio) was added to the boronate ester E8aa (1.30 equivalents), P4 (1.00 equivalents, product of step 7), potassium acetate (2.00 equivalents, CAS: 127-08-2) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 equivalents, CAS 72287-26-4). The reaction mixture was stirred at 80°C until complete conversion of P4 was achieved as judged by GC / MS and TLC. After cooling to room temperature, water was added, followed by extraction with dichloromethane and water. The combined organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was heated to reflux in ethanol for 2 hours and washed with ethanol while hot filtering. The hot filtration step was then repeated with a 1:1 mixture of methanol and water to obtain the product P8aa as a solid.

[0457] Step 15

[0458] Under nitrogen atmosphere in anhydrous THF, E4 (1.30 equivalents) and subsequently P8aa (1.00 equivalents, the product of step 14) are added to NaH (1.40 equivalents, CAS: 7646-69-7), and stirred under reflux until the reaction is complete (monitoring the reaction via GC / MS and TLC). Subsequently, the reaction mixture is poured into water and ice. Extracted with dichloromethane, the organic layer then combined with charcoal treatment, filtered, and the solvent removed under reduced pressure. Purification of the crude product is carried out by column chromatography or recrystallization to obtain the product M5 as a solid.

[0459] Steps for the Synthesis of Scheme VI

[0460] Step 16

[0461] E9 (1.00 equivalent) and E1 (1.00 equivalent) were stirred at 105° C. in anhydrous dioxane under a nitrogen atmosphere until the reaction was complete (reaction monitored via GC / MS and TLC). After cooling to room temperature, water was added and then extracted with dichloromethane and water. The combined organic layers were dried over anhydrous MgSO 4 and concentrated under reduced pressure. The crude product was heated to reflux for 2 hours in ethanol and washed with ethanol during heat filtration. P4 was obtained as a solid.

[0462] Step 17

[0463] This step is similar to step 14 above, except that THF is used instead of ethanol for the hot filtration step.

[0464] Step 18

[0465] This step is similar to step 15 above.

[0466] Steps for the Synthesis of Scheme VII

[0467] Step 19

[0468] This step is similar to step 1 above.

[0469] Step 20

[0470] Under nitrogen atmosphere, P1 (1.00 equivalent), E7 (3.00 equivalent) and tripotassium phosphate (4.00 equivalent) were suspended in anhydrous DMSO and stirred at 110° C. for 2 hours (reaction monitored via GC / MS and TLC). Subsequently, the reaction mixture was poured into a stirred mixture of water and ice. The resulting precipitate was filtered off and washed with water and ethanol. The crude product was purified by additional washing with dichloromethane to obtain M6 as a solid.

[0471] Cyclic voltammetry

[0472] Cyclic voltammograms were obtained by mixing the voltammograms with a concentration of 10 -3 The measurement was performed at room temperature under nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and using FeCp2 / FeCp2 + The HOMO data were calibrated using ferrocene as an internal standard using a saturated calomel electrode (SCE).

[0473] Density functional theory calculations

[0474] The molecular structure was optimized using the BP86 functional and the resolution of identity approach (RI). Excitation energies were calculated using the BP86-optimized structure using time-dependent DFT (TD-DFT). Orbital and excited-state energies were calculated using the B3LYP functional. The Def2-SVP basis set and an m4 grid were used for numerical integration. The Turbomole package was used for all calculations.

[0475] Photophysical measurements

[0476] Sample pretreatment: spin coating.

[0477] Instrument: Spin150, SPS euro.

[0478] The sample concentration was 0.2 mg / mL and was dissolved in toluene / DCM as a suitable solvent.

[0479] Program: 7 to 30 seconds at 2000 rpm. After coating, the film was dried at 70° C. for 1 minute.

[0480] Absorption measurement

[0481] The wavelength of the sample's absorption maximum in the wavelength region above 270 nm was determined using a Thermo Scientific Evolution 201 UV-visible spectrophotometer. This wavelength was used as the excitation wavelength for photoluminescence spectroscopy and quantum yield measurements.

[0482] Photoluminescence and phosphorescence spectroscopy

[0483] For analysis of phosphorescence spectra and photoluminescence spectra, a fluorescence spectrometer “Fluoromax 4P” from Horiba was used.

[0484] Time-resolved PL spectroscopy in the μs range and ns range (FS5)

[0485] Time-resolved PL measurements were performed on an FS5 fluorescence spectrometer from Edinburgh Instrument. The better light collection allows an optimized signal-to-noise ratio compared to measurements on a HORIBA device, which favors the FS5 system, especially for transient PL measurements of delayed fluorescence properties. The spectrometer includes a 150 W xenon arc lamp as a continuous light source and the selected wavelength can be selected by a Czerny-Turner monochromator. However, standard measurements were performed instead using an external VPLED variable pulse LED with an emission wavelength of 310 nm. The sample emission was directed to a sensitive R928P photomultiplier tube (PMT) allowing the detection of single photons with a peak quantum efficiency of up to 25% in the spectral range between 200 nm and 870 nm. The detector is a temperature-stabilized PMT providing dark counts below 300 cps (counts per second). Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions was applied. By substituting the corresponding amplitude A for the specific lifetime i For a specific lifetime τ i Weighted,

[0486]

[0487] Determine the delayed fluorescence lifetime τ DF .

[0488] Photoluminescence quantum yield measurement

[0489] For photoluminescence quantum yield (PLQY) measurements, an absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yield and CIE coordinates were determined using software U6039-05 version 3.6.0.

[0490] The emission maximum is given in nm, the quantum yield Φ is given in %, and the CIE coordinates are given as x-values, y-values.

[0491] Determine PLQY using the following protocol:

[0492] 1) Quality assurance: using anthracene in ethanol (known concentration) as a reference

[0493] 2) Excitation wavelength: Determine the absorption maximum of organic molecules and use this wavelength to excite organic molecules

[0494] 3) Measurement

[0495] The quantum yield was measured for samples of film (10 wt% emitter in PMMA) under nitrogen atmosphere. The yield was calculated using the equation:

[0496]

[0497] Among them, n 光子 represents photon counts and Int. represents intensity. For quality assurance, anthracene in ethanol (known concentration) was used as a reference.

[0498] TCSPC (Time-Correlated Single Photon Counting)

[0499] Excited state population dynamics were determined using an Edinburgh Instruments FS5 fluorescence spectrophotometer equipped with an emission monochromator, a temperature-stabilized photomultiplier tube as detector unit, and a pulsed LED (310 nm center wavelength, 910 ps pulse width) as excitation source. The samples were placed in cuvettes and flushed with nitrogen during the measurements.

[0500] Full decay dynamics

[0501] The full excited state population decay dynamics over several orders of magnitude in time and signal intensity were achieved by performing TCSPC measurements in four time windows: 200 ns, 1 μs, and 20 μs, as well as longer measurements spanning >80 μs. The measured time curves were then processed in the following way:

[0502] 1. Apply background correction by determining the mean signal level before excitation and subtraction.

[0503] 2. Align the time axis using the initial rise of the main signal as a reference.

[0504] 3. Scale the curves onto each other using overlapping measurement time zones.

[0505] 4. Merge the processed curves into one curve.

[0506] Data Analysis

[0507] Data analysis was performed using single or double exponential fitting of the transient fluorescence (PF) and delayed fluorescence (DF) decays, respectively. The ratio of delayed fluorescence to transient fluorescence (n value) was calculated by integrating the corresponding photoluminescence decays over time.

[0508]

[0509] The average excited-state lifetime was calculated by taking the average of the transient and delayed fluorescence decay times, weighted by the respective contributions of PF and DF.

[0510] Fabrication and characterization of optoelectronic devices

[0511] OLED devices including the organic molecules of the present invention can be fabricated via vacuum deposition. If a layer contains more than one compound, the weight percentage of the compound or compounds is given in %. The total weight percentage value is 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0512] The non-optimized OLEDs were characterized using standard methods and measuring electroluminescence spectra and intensity-dependent external quantum efficiency (in %), which was calculated using the light detected by the photodiode and the current. The OLED device lifetime was derived from the change in luminance during operation at a constant current density. The LT50 value corresponds to the time point at which the measured luminance drops to 50% of the initial luminance. Similarly, the LT80 value corresponds to the time point at which the measured luminance drops to 80% of the initial luminance, the LT97 value corresponds to the time point at which the measured luminance drops to 97% of the initial luminance, and so on.

[0513] (e.g., using an increased current density) to perform accelerated lifetime measurements. For example, the following equation is used to determine the lifetime at 500 cd / m 2 The following LT80 values:

[0514]

[0515] Where L0 represents the initial brightness under the applied current density.

[0516] This value corresponds to the average of several (typically 2 to 8) pixels, giving the standard deviation between these pixels.The figure shows a data series for one OLED pixel.

[0517] HPLC-MS

[0518] The analysis was performed on HPLC-MS by Agilent (HPLC 1260 Infinity) with MS detector (single quadrupole).

[0519] For example, a typical HPLC method is as follows: a reverse phase column from Agilent, 3.0 mm × 100 mm, with a particle size of 2.7 μm (Poroshell 120EC-C18, 3.0 mm × 100 mm, 2.7 μm HPLC column) is used in HPLC. HPLC-MS measurements are performed at 45° C., typically with the following gradient:

[0520]

[0521] The following solvent mixtures were used (all solvents contained 0.1% (V / V) formic acid):

[0522] Solvent A: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent B: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent C: THF (50%) MeCN (50%)

[0523] The measurement was performed using an injection volume of 2 μL of a solution having an analyte concentration of 0.5 mg / mL.

[0524] Ionization of the probe was performed using an atmospheric pressure chemical ionization (APCI) source in positive (APCI+) or negative (APCI-) ionization mode or an atmospheric pressure photoionization (APPI) source.

[0525] Example 1

[0526]

[0527] Example 1 was synthesized according to Step 1 (yield 64%) and Step 4 (yield 32%).

[0528] MS (HPLC-MS), m / z (retention time): 589.6 (5.53 minutes).

[0529] Figure 1 The emission spectrum of Example 1 (10 wt. % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 478 nm. The photoluminescence quantum yield (PLQY) is 79%, the full width at half maximum (FWHM) is 0.43 eV, and the emission lifetime is 25.8 μs. The resulting CIE x The coordinates are determined at 0.18, CIE y The coordinates are determined at 0.31.

[0530] Example 2

[0531]

[0532] Example 2 was synthesized according to Step 1 (yield 64%), Step 2 (yield 52%), and Step 3 (yield 27%).

[0533] MS (HPLC-MS), m / z (retention time): 741.7 (5.53 minutes).

[0534] Figure 2 The emission spectrum of Example 2 (10 wt. % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 485 nm. The photoluminescence quantum yield (PLQY) is 59%, the full width at half maximum (FWHM) is 0.45 eV, and the emission lifetime is 21.3 μs. The resulting CIE x The coordinates are determined at 0.21, CIE y The coordinate is determined at 0.36.

[0535] Example 3

[0536]

[0537] Example 3 was synthesized according to Step 5 (yield 32%) and Step 6 (yield 59%).

[0538] MS (HPLC-MS), m / z (retention time): 678.7 (5.00 min).

[0539] Figure 3 The emission spectrum of Example 3 (10 wt. % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 482 nm. The photoluminescence quantum yield (PLQY) is 74%, the full width at half maximum (FWHM) is 0.47 eV, and the emission lifetime is 28.6 μs. The resulting CIE x The coordinates are determined at 0.19, CIE y The coordinate is determined at 0.32.

[0540] Example 4

[0541]

[0542] Example 4 was synthesized according to Step 7 (yield 60%), Step 8 (yield 89%), and Step 9 (yield 79%).

[0543] MS (HPLC-MS), m / z (retention time): 754.8 (5.80 min).

[0544] Figure 4The emission spectrum of Example 4 (10 wt % in PMMA) at room temperature (ie approximately 20° C.) is depicted. max ) at 528 nm. The full width at half maximum (FWHM) is 0.52 eV, and the emission lifetime is 10.8 μs. The resulting CIE x The coordinates are determined at 0.34, CIE y The coordinate is determined at 0.50.

[0545] Example 5

[0546]

[0547] Example 5 was synthesized according to Step 11 (yield 88%, step 10 was not performed since E8 was commercially available in this case) and Step 12 (yield 48%).

[0548] MS (HPLC-MS), m / z (retention time): 843.9 (6.51 min).

[0549] Figure 5 The emission spectrum of Example 5 (10 wt % in PMMA) at room temperature (ie approximately 20° C.) is depicted. max ) at 527 nm. The full width at half maximum (FWHM) is 0.56 eV, and the emission lifetime is 8.0 μs. The resulting CIE x The coordinates are determined at 0.34, CIE y The coordinates are determined at 0.49.

[0550] Example 6

[0551]

[0552] Example 6 was synthesized according to the steps using 2-bromobiphenyl (CAS: 2052-07-5) as step 13 of E1aa (yield 10%), carbazole (CAS: 86-74-8) as step 7 of E3 (yield 41%), 3-cyano-4-fluorophenylboronic acid (CAS: 214210-21-6) as step 8 of E8 (yield 17%), and 5,12-dihydro-5-phenyl-indolo[3,2-a]carbazole (CAS: 1247053-55-9) as step 9 of E4 (yield 30%).

[0553] MS (HPLC-MS), m / z (retention time): 830.9 (5.88 minutes).

[0554] Figure 6 The emission spectrum of Example 6 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted.max ) at 520 nm. The full width at half maximum (FWHM) is 0.51 eV, and the emission lifetime is 12.7 μs. The resulting CIE x The coordinates are determined at 0.31, CIE y The coordinate is determined at 0.50.

[0555] Example 7

[0556]

[0557] Example 7 was synthesized according to Step 14 (yield 74%) using 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbamyl (CAS: 1268244-56-9) and 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS: 863868-29-59) as P4 and E8aa, respectively, and Step 15 (yield 62%) using 3H-3-purinodiphenyl[g,ij]naphtho[2,1,8-cde]azulene (CAS: 2408302-78-1) as E4.

[0558] MS (HPLC-MS), m / z (retention time): 713.6 (4.97 minutes).

[0559] Figure 7 The emission spectrum of Example 7 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 541 nm. The full width at half maximum (FWHM) is 0.51 eV. The resulting CIE x The coordinates are determined at 0.39, CIE y The coordinates are determined at 0.53.

[0560] Example 8

[0561]

[0562] Example 8 was synthesized according to step 13a using 9-(4,6-dichloro-[1,3,5]triazin-2-yl)carbazole (CAS: 24209-95-8) and phenyl-d5-boronic acid (CAS: 215527-70-1) as E6aa and E7aa, respectively (yield 47%), step 14 using 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS: 863868-29-59) as E8aa (yield 69%), and step 15 using carbazole (CAS: 86-74-8) as E4 (yield 41%).

[0563] MS (HPLC-MS), m / z (retention time): 594.6 (4.46 minutes).

[0564] Figure 8 The emission spectrum of Example 8 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 479 nm. The photoluminescence quantum yield (PLQY) is 78%, the full width at half maximum (FWHM) is 0.44 eV, and the emission lifetime is 29.3 μs. The resulting CIE x The coordinates are determined at 0.18, CIE y The coordinates are determined at 0.31.

[0565] Example 9

[0566]

[0567] Example 9 was synthesized by using 2,4-dichloro-6-phenyl-1,3,5-triazine (CAS: 1700-02-3) and 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS: 863868-29-5) as step 1 of E1 and E2 (yield 42%), respectively, and using 9H-carbazole-3-carbonitrile (3.00 equivalents, CAS: 57102-93-9) as step 2 of E3 (yield 38%), while reacting at 120° C. to directly obtain M1 as a product.

[0568] MS (HPLC-MS), m / z (retention time): 639.6 (3.50 minutes).

[0569] Figure 9 The emission spectrum of Example 9 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 468 nm. The photoluminescence quantum yield (PLQY) is 71%, the full width at half maximum (FWHM) is 0.44 eV, and the emission lifetime is 38.0 μs. The resulting CIE x The coordinates are determined at 0.17, CIE y The coordinates are determined at 0.22.

[0570] Example 10

[0571]

[0572] Example 10 was synthesized according to Step 19 (38% yield) using 2,4-dichloro-6-phenyl-1,3,5-triazine (CAS: 1700-02-3) and 5-cyano-2-fluorophenylboronic acid (CAS: 468718-30-1) as E1 and E8aa, respectively, and Step 20 (26% yield) using 9H-carbazole-1,2,3,4-d4 (3.00 equiv, CAS: 935425-39-1) as E7. M7 was obtained as a solid. MS (HPLC-MS), m / z (retention time): 597.7 (4.341 min).

[0573] Figure 10 The emission spectrum of Example 10 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 479 nm. The photoluminescence quantum yield (PLQY) is 76%, the full width at half maximum (FWHM) is 0.43 eV, and the emission lifetime is 28.9 μs. The resulting CIE x The coordinates are determined at 0.18, CIE y The coordinate is determined at 0.32.

[0574] Example 11

[0575]

[0576] Example 11 was synthesized according to Step 16 (yield 57%) using carbazole potassium salt (CAS: 6033-87-0) as E9 and 2,4-dichloro-6-phenyl-1,3,5-triazine (CAS: 1700-02-3) as E1, Step 17 (yield 58%) using 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS: 863868-29-5) as E8aa, and Step 18 (yield 57%) using 3-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole (CAS: 1313391-57-9) as E4. MS (HPLC-MS), m / z (retention time): 820.9 (6.137 min).

[0577] Figure 11 The emission spectrum of Example 11 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 482 nm. The photoluminescence quantum yield (PLQY) is 58%, the full width at half maximum (FWHM) is 0.43 eV, and the emission lifetime is 33.3 μs. The resulting CIE x The coordinates are determined at 0.19, CIE y The coordinate is determined at 0.32.

[0578] Example 12

[0579]

[0580] Example 12 was synthesized according to Step 13 (yield 53.5%) using 9-(4,6-dichloro-1,3,5-triazin-2-yl)-carbazole (CAS: 24209-95-8) as E6aa and dibenzo[b,d]furan-2-ylboronic acid (CAS: 402936-15-6) as E7aa, and purifying the crude product by two hot filtration steps using ethanol and a 1:1 mixture of methanol and water; Step 14 (yield 67.1%) using 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (CAS: 863868-29-5) as E8aa; and Step 15 (yield 66.5%) using carbazole (CAS: 86-74-8) as E4.

[0581] MS (HPLC-MS), m / z (retention time): 679.8 (5.238 minutes).

[0582] Figure 12 The emission spectrum of Example 12 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 478 nm. The photoluminescence quantum yield (PLQY) is 77%, the full width at half maximum (FWHM) is 0.43 eV, and the emission lifetime is 29.7 μs. The resulting CIE x The coordinates are determined at 0.18, CIE y The coordinates are determined at 0.31.

[0583] Example 13

[0584]

[0585] Example 13 was synthesized according to Step 13 (yield 53.5%) using 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole (CAS: 24209-95-8) as E6aa and dibenzo[b,d]furan-2-ylboronic acid (CAS: 402936-15-6) as E7aa, Step 14 (yield 77.9%) using 3-cyano-4-fluorophenylboronic acid (CAS: 214210-21-6) as E8aa, and Step 17 (yield 35.2%) using 5,12-dihydro-5-phenyl-indolo[3,2-a]carbazole (CAS: 1247053-55-9) as E4.

[0586] MS (HPLC-MS), m / z (retention time): 845.0 (6.613 minutes).

[0587] Figure 13 The emission spectrum of Example 13 (10 wt % in PMMA) at room temperature (ie, approximately 20° C.) is depicted. max ) at 537 nm. The photoluminescence quantum yield (PLQY) is 35%, the full width at half maximum (FWHM) is 0.49 eV, and the emission lifetime is 21.9 μs. The resulting CIE x The coordinates are determined at 0.36, CIE y The coordinates are determined at 0.53.

[0588] Device Examples

[0589] Stacking materials

[0590]

[0591] Device Architecture

[0592] Table 1. Exemplary optoelectronic device (OLED) settings A.

[0593]

[0594]

[0595] Table 2. Settings B for exemplary optoelectronic devices (OLEDs).

[0596]

[0597] Table 3. Settings C for exemplary optoelectronic devices (OLEDs).

[0598]

[0599]

[0600] Table 4. Exemplary optoelectronic devices (OLEDs).

[0601]

[0602]

[0603] Device Results

[0604] Table 5. Device results for all optoelectronic devices (OLEDs) listed in Table 4.

[0605]

[0606] Compared to similar OLEDs using eg comparative example 1 as TADF emitters in the emission layer, the organic molecules according to the invention lead to optoelectronic devices with an extended lifetime while exhibiting a high external quantum efficiency (EQE) and a similar color point.

[0607] Additional Examples of Inventive Organic Molecules

[0608]

[0609]

[0610]

[0611]

[0612]

[0613]

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620]

[0621]

[0622]

[0623]

[0624]

[0625]

[0626]

[0627]

[0628]

[0629]

[0630]

[0631]

[0632]

[0633]

[0634]

[0635]

[0636]

[0637] 。

Claims

1. An optoelectronic device comprising an organic molecule comprising a first chemical moiety and a second chemical moiety as an emitter, in, The first chemical moiety comprises the structure of Formula Ia: The second chemical moiety includes a structure according to any one of Formula II-a-1, Formula II-a-5, Formula II-a-9, Formula II-a-10, Formula II-a-11, Formula II-a-12, Formula II-a-13, and Formula II-a-14: in, The first chemical moiety is linked to the second chemical moiety via a single bond; T is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, or R 2 ; V is hydrogen; W is the binding site of the single bond connecting the first chemical moiety to the second chemical moiety, or R 2 ; X in Formula Ia is R X ; Y is R 2 ; R X Selected from the group consisting of CN and CF3; R 1 Selected from the group consisting of: and C6-C 18 Aryl, optionally substituted with one or more substituents R 3 ; R 2 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; and C1-C 10 an alkyl group in which one or more hydrogen atoms are optionally replaced by deuterium; R 3 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; Cl; Br; I; and C1-C5 alkyl, optionally substituted with one or more substituents R 4 ; R a 、R c and R d is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; Cl; Br; I; and C1-C5 alkyl, optionally substituted with one or more substituents R 8 ; Among them, the two parts R b Form a direct bond; R 8 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; Cl; Br; I; and C1-C5 alkyl, optionally substituted with one or more substituents R 9 ; # represents the binding site of the first chemical moiety and the second chemical moiety; X in formula II-a-9, formula II-a-10, formula II-a-11, formula II-a-12, formula II-a-13 and formula II-a-14 is NR 16 ; R 16 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; t Bu; and Ph, wherein one or more hydrogen atoms are optionally replaced by deuterium, Me, i Pr, t Bu and Ph substitution; R f and R g is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; Cl; Br; I; C1-C5 alkyl, optionally substituted with one or more substituents R 13 ; and C3-C 15 Heteroaryl, optionally substituted with one or more substituents R 13 ; R 13 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; Br; I; C1-C5 alkyl, optionally substituted with one or more substituents R 14 ; and C6-C 18 Aryl, optionally substituted with one or more substituents R 14 ; R 4 、R 9 、R 14 and R 15 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; and C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, CN, CF3 or F; And among them, Exactly one substituent selected from the group consisting of T and W represents the binding site of the single bond connecting the first chemical moiety to the second chemical moiety.

2. The optoelectronic device according to claim 1, wherein R 1 Selected from the group consisting of: and C6-C 18 Aryl, optionally substituted with one or more substituents R 3 ; R 3 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; and C1-C5 alkyl, optionally substituted with one or more substituents R 4 ; R 2 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; and C1-C5 alkyl, wherein one or more hydrogen atoms are optionally substituted with deuterium; R a 、R c and R d is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; and C1-C5 alkyl, optionally substituted with one or more substituents R 8 ; R 8 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; and C1-C5 alkyl, optionally substituted with one or more substituents R 9 ; R 4 and R 9 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CF3; CN; F; and C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently replaced by deuterium.

3. The optoelectronic device according to claim 1, wherein R 1 Selected from the group consisting of: and Ph, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu or CN substitution; R 2 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; Me; i Pr; and t Bu; R a 、R c and R d is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; and t Bu.

4. The optoelectronic device according to one or more of claims 1 to 3, wherein R f and R g independently selected at each occurrence from the group consisting of: hydrogen; deuterium; F; CF3; CN; and C3-C 15 Heteroaryl, wherein one or more hydrogen atoms are optionally independently replaced by deuterium, Me, i Pr, t Bu, CF3, CN or Ph substitution; R 15 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; CN; Me; i Pr; and t Bu.

5. The optoelectronic device according to one or more of claims 1 to 3, wherein R X In each occurrence is CN.

6. The optoelectronic device according to one or more of claims 1 to 3, wherein The organic molecule is selected from the following compounds:

7. An optoelectronic device comprising an organic molecule as an emitter, wherein: The organic molecule is selected from the following compounds:

8. Use of the organic molecule according to any one of claims 1 to 7 as a luminescent emitter in an optoelectronic device.

9. The use according to claim 8, wherein: The optoelectronic device is selected from the group consisting of: Light-emitting electrochemical cells; Organic solar cells; Organic transistors; organic lasers; and Down-conversion components.

10. The use according to claim 8, wherein: The optoelectronic device is an organic diode.

11. The use according to claim 8, wherein: The optoelectronic device is an organic light emitting diode.

12. The use according to claim 8, wherein: The optoelectronic device is an organic light emitting diode sensor.

13. The use according to claim 8, wherein: The optoelectronic device is an organic field effect transistor.

14. A composition comprising: (a) Organic molecules according to one or more of claims 1 to 7 in the form of emitters; and (b) an emitter different from the organic molecule; and (c) optionally, a host material different from the organic molecule; and (d) optionally, one or more dyes; and (e) Optionally, one or more solvents.

15. The composition according to claim 14, comprising the following ingredients: (i) 1 to 50 wt% of an organic molecule according to any one of claims 1 to 7; (ii) 5 wt% to 98 wt% of a first host compound; (iii) 1% to 30% by weight of at least one further emitter molecule having a structure different from that of the organic molecule; as well as (iv) optionally, 0% to 94% by weight of at least one second host compound having a structure different from that of the organic molecule; as well as (v) optionally, 0% to 94% by weight of a solvent, wherein the sum of the components of the composition is 100 wt %.

16. A composition comprising: (a) organic molecules according to one or more of claims 1 to 7 in the form of emitters; and (b) a host material different from the organic molecule; and (c) optionally, one or more dyes; and (d) Optionally, one or more solvents.

17. An optoelectronic device comprising the composition according to any one of claims 14 to 16, in the form of a device selected from the group consisting of a light-emitting electrochemical cell, an organic solar cell, an organic transistor, an organic laser, and a down-conversion element. The optoelectronic device according to claim 17 , which is an organic light emitting diode.

19. The optoelectronic device of claim 17, which is an organic light emitting diode sensor.

20. The optoelectronic device of claim 17, which is an organic diode.

21. The optoelectronic device of claim 17, which is an organic field effect transistor.

22. The optoelectronic device according to claim 17, comprising: substrate; anode; and a cathode, wherein the anode or the cathode is disposed on the substrate; as well as A light-emitting layer is disposed between the anode and the cathode and includes the composition.

23. A method for manufacturing an optoelectronic device, wherein: Using an organic molecule according to any one of claims 1 to 7 as an emitter or a composition according to any one of claims 14 to 16, the method comprises the step of processing the organic molecule using vacuum evaporation or from solution.

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