Organic molecules for optoelectronic devices

Abstract

The present invention relates to organic molecules for use in optoelectronic devices. The organic molecule is a first chemical moiety comprising the structure of formula I: [Formula 1] JPEG2023544435000198.jpg4361 ...Chemical formula I - a second chemical moiety comprising the structure of formula II: [chemical 2] JPEG2023544435000199.jpg4543 ...Chemical formula II wherein the first chemical moiety is attached to the second chemical moiety via a single bond; # is the site of attachment of the first chemical moiety to the second chemical moiety; R a , R b and R c is a single bond attachment site linking a second chemical moiety to said first chemical moiety; m is 0 or 1, n is 0 or 1, and m+n=1; wherein at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV , R V and R VI , R VI and R VII , R VII and R VIII , R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIIIis fused to adjacent benzene rings a, b, c or d of formula I and optionally contains one or more substituents R 9 Forms an aromatic ring system substituted with

Description

[Technical Field]

[0001] The present invention relates to organic light-emitting molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]

[0002] The problem that the present invention aims to solve is to provide molecules that are suitable for use in optoelectronic devices. [Means for solving the problem]

[0003] Such objectives are achieved by the present invention, which provides novel organic molecules.

[0004] Organic electroluminescent devices, including one or more light-emitting layers using organic materials, such as organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors, are becoming increasingly important. In particular, OLEDs are promising devices for electronic products such as screens, displays, and lighting devices. In contrast to most electroluminescent devices that use essentially inorganic materials, organic electroluminescent devices using organic materials are usually flexible and can be produced, especially in thin films. Currently available OLED-based screens and displays offer excellent efficiency and long lifetimes, or excellent color purity and long lifetimes, but do not combine all three of these properties.

[0005] Therefore, there is an unmet need in the technology for optoelectronic devices that have high quantum yield, long lifetime, and excellent color purity.

[0006] The color purity or color point of an OLED is typically given by CIEx and CIEy coordinates, while the color gamut of next-generation displays is given by so-called BT-2020 and DCPI3 values. To achieve such color coordinates, a top-emitting device typically requires a cavity modification to adjust the color coordinates. To achieve high efficiency in a top-emitting device while targeting such a color gamut, a narrow emission spectrum is required in a bottom-emitting device. [Effects of the Invention]

[0007] The organic molecules of the present invention exhibit emission maxima in the deep blue, sky blue, green, or yellow spectral range, preferably in the deep blue, sky blue, and green spectral range, and most preferably in the green spectral range. The organic molecules exhibit emission maxima, particularly in the range of 420 to 580 nm, preferably 440 to 560 nm, more preferably 470 to 550 nm, and particularly preferably 500 to 540 nm. Furthermore, the molecules of the present invention exhibit narrow emission, as indicated by a small full width at half maximum (FWHM). The emission spectrum of the organic molecules, typically measured at room temperature (i.e., about 25°C) in PMMA (poly(methyl methacrylate)) containing 2% by weight of the emitter, preferably exhibits a full width at half maximum (FWHM) of 0.25 eV or less (≦0.25 eV). The photoluminescence quantum yield of the organic molecules of the present invention is particularly 10% or more.

[0008] The use of the molecules according to the invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), results in narrow emission and high efficiency of the device. The corresponding OLEDs have higher stability than OLEDs with known emitter materials and similar hues, and / or, when using the molecules according to the invention in OLED displays, a more accurate reproduction of natural-looking hues, i.e., a higher resolution of the displayed image, is achieved. In particular, the molecules can be used in combination with energy pumps to enable so-called hyperfluorescence or hyperphosphorescence. In this case, other species contained in the optoelectronic device transfer energy to the organic molecules of the invention, which then emit light. [Brief explanation of the drawings]

[0009] [Figure 1] 1 shows the emission spectrum of Example 1 (2 wt %) in PMMA. [Figure 2] 1 shows the emission spectrum of Example 2 (2 wt %) in PMMA. DETAILED DESCRIPTION OF THE INVENTION

[0010] The organic molecule according to the present invention comprises or consists of: one first chemical moiety comprising or consisting of the structure of formula I: [ka] ...Chemical formula I - one second chemical moiety comprising or consisting of the structure of formula II: [ka] ...Chemical formula II wherein the first chemical moiety is attached to the second chemical moiety via a single bond. # is the attachment site between the first chemical moiety and the second chemical moiety. m is 0 or 1, and n is 0 or 1. R a is a single bond attachment site connecting said second chemical moiety to said first chemical moiety, or R A is. R b is a single bond attachment site connecting said second chemical moiety to said first chemical moiety, or R B is. R c is a single bond attachment site connecting said second chemical moiety to said first chemical moiety, or R X is. R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV , R XV , R XVI , R XVII and R XVIII are independently selected from the group consisting of: Hydrogen, deuterium, N(R 9 )2, OR 9 , S.R. 9 , Si(R 9 )3, B(OR 9 )2, OSO2R 9 , CF3, CN, halogens (F, Cl, Br, I), Optionally, one or more substituents R 9 C1-C substituted with 40 Alkyl, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 9 C1-C substituted with 40 Alkoxy, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 9 C1-C substituted with 40 thioalkoxy, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 9 C2-C substituted with 40 alkenyl, wherein one or more non-adjacent CH groups are optionally joined 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)(R9 ), SO, SO2, NR 9 , O, S or CONR 9 is replaced by Optionally, one or more substituents R 9 C2-C substituted with 40 Alkynyl, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 9 C6-C substituted with 60 aryl, and Optionally, one or more substituents R 9 C3-C substituted with 57 heteroaryl, wherein at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV , R V and R VI , R VI and R VII , R VII and R VIII , R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIIIis fused to adjacent benzene rings a, b, c or d of formula I and optionally contains one or more substituents R 9 forming an aromatic ring system substituted with where R I and R XVIII Not only R VIII and R IX Each pair of 1 which in each case form a direct bond, CR 9 R 10 , C=CR 9 R 10 , C=O, C=NR 9 , N.R. 9 , O, SiR 9 R 10 , S, S(O) and S(O)2. R A , R B , R X and R 1 -R 8 are independently selected from the group consisting of: Hydrogen, deuterium, N(R 11 )2, OR 11 , S.R. 11 , Si(R 11 )3, B(OR 11 )2, OSO2R 11 , CF3, CN, halogens (F, Cl, Br, I), Optionally, one or more substituents R 11 C1-C substituted with 40 Alkyl, wherein one or more non-adjacent CH groups are optionally joined by R 11 C=CR 11 , C≡C, Si(R 11 )2, Ge(R 11 )2, Sn(R 11 )2, C=O, C=S, C=Se, C=NR 11 , P(=O)(R 11 ), SO, SO2, NR 11 , O, S or CONR 11 is replaced by Optionally, one or more substituents R 11 C1-C substituted with 40Alkoxy, wherein one or more non-adjacent CH groups are optionally joined by R 11 C=CR 11 , C≡C, Si(R 11 )2, Ge(R 11 )2, Sn(R 11 )2, C=O, C=S, C=Se, C=NR 11 , P(=O)(R 11 ), SO, SO2, NR 11 , O, S or CONR 11 is replaced by Optionally, one or more substituents R 11 C1-C substituted with 40 thioalkoxy, wherein one or more non-adjacent CH groups are optionally joined by R 11 C=CR 11 , C≡C, Si(R 11 )2, Ge(R 11 )2, Sn(R 11 )2, C=O, C=S, C=Se, C=NR 11 , P(=O)(R 11 ), SO, SO2, NR 11 , O, S or CONR 11 is replaced by Optionally, one or more substituents R 11 C2-C substituted with 40 alkenyl, wherein one or more non-adjacent CH groups are optionally joined by R 11 C=CR 11 , C≡C, Si(R 11 )2, Ge(R 11 )2, Sn(R 11 )2, C=O, C=S, C=Se, C=NR 11 , P(=O)(R 11 ), SO, SO2, NR 11 , O, S or CONR 11 is replaced by Optionally, one or more substituents R 11 C2-C substituted with 40 Alkynyl, wherein one or more non-adjacent CH groups are optionally joined by R 11 C=CR 11, C≡C, Si(R 11 )2, Ge(R 11 )2, Sn(R 11 )2, C=O, C=S, C=Se, C=NR 11 , P(=O)(R 11 ), SO, SO2, NR 11 , O, S or CONR 11 is replaced by Optionally, one or more substituents R 11 C6-C substituted with 60 aryl, and Optionally, one or more substituents R 11 C3-C substituted with 57 heteroaryl, where R 2 and R 3 Not only R X and R 7 Each pair of 2 This forms, in each case, CR 12 R 13 , C=CR 12 R 13 , C=O, C=NR 12 , N.R. 12 , O, SiR 12 R 13 , S, S(O) and S(O)2, wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 is fused to the adjacent benzene ring e or f of formula II and optionally contains one or more substituents R 11forming an aromatic or aliphatic, carbocyclic or heterocyclic ring system substituted with R 12 and R 13 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R 14 )2, OR 14 , S.R. 14 , Si(R 14 )3, B(OR 14 )2, OSO2R 14 , CF3, CN, halogens (F, Cl, Br, I), Optionally, one or more substituents R 14 C1-C substituted with 40 Alkyl, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 14 C1-C substituted with 40 Alkoxy, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 14 C1-C substituted with 40 thioalkoxy, wherein one or more non-adjacent CH groups are optionally joined by R 14 C=CR14 , 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 is replaced by Optionally, one or more substituents R 14 C2-C substituted with 40 alkenyl, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 14 C2-C substituted with 40 Alkynyl, wherein one or more non-adjacent CH groups are optionally joined 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 is replaced by Optionally, one or more substituents R 14 C6-C substituted with 60 aryl, and Optionally, one or more substituents R 14 C3-C substituted with 57 heteroaryl, wherein optionally, two or more substituents R 12 and / or R 13form an aliphatic or aromatic, carbocyclic or heterocyclic ring system containing from 5 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from the group consisting of N, O and S. R 9 , R 10 , R 11 and R 14 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh (Ph = phenyl), SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C3-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl). According to the present invention, R a , R b and Rc is a single bond attachment site linking a second chemical moiety to said first chemical moiety; Also, according to the present invention, m+n=1.

[0011] In one embodiment of the present invention, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV , R XV , R XVI , R XVII and R XVIII are each independently selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C3-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl), wherein at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV , R V and R VI , R VI and R VII , R VII and R VIII is fused to adjacent benzene rings a or b of formula I and optionally contains one or more substituents R 9 forming an aromatic ring system substituted with wherein each benzene ring a or b and any additional ring or rings formed by adjacent substituents, and any fused ring system or systems thus formed, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and RIX Each pair of 1 which is a direct bond in each case.

[0012] In a preferred embodiment of the present invention, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV , R XV , R XVI , R XVII and R XVIII are each independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; and N(Ph)2, wherein at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV , R V and R VI , R VI and R VII , R VII and R VIII are fused to the adjacent benzene ring a or b of formula I to form an aromatic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr,t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring a or b and any additional ring or rings formed by adjacent substituents, and any fused ring system or systems thus formed, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX Each pair of 1 which is a direct bond in each case.

[0013] In a more preferred embodiment of the present invention, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV , R XV , R XVI , R XVII and R XVIII are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV , R V and R VI , R VI and R VII , R VII and R VIII are fused to the adjacent benzene ring a or b of formula I to form an aromatic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring a or b and any fused ring system or systems thus formed, composed of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , RXVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX Each pair of 1 which is a direct bond in each case.

[0014] In a particularly preferred embodiment of the present invention, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV , R XV , R XVI , R XVII and R XVIII are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; wherein at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV , R V and R VI , R VI and R VII , R VII and R VIII are fused to the adjacent benzene ring a or b of formula I to form an aromatic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; wherein each benzene ring a or b and any fused ring system or systems thus formed, composed of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX Each pair of 1 which is a direct bond in each case.

[0015] In a preferred embodiment of the present invention, at least one pair of adjacent groups R I and R II , R II and R III , R III and R IV forms an aromatic ring system fused to the adjacent benzene ring a, At least one pair of adjacent groups R V and R VI , R VI and R VII, R VII and R VIII forms an aromatic ring system fused to the adjacent benzene ring b of formula I, wherein both of the fused ring systems thus formed are optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring a or b and the additional ring or rings formed by adjacent substituents, so formed, fused ring system or systems, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX Each pair of 1 which is a direct bond in each case.

[0016] In a more preferred embodiment of the present invention, at least one pair of adjacent groups R I and R II , R II and RIII , R III and R IV forms an aromatic ring system fused to the adjacent benzene ring a, At least one pair of adjacent groups R V and R VI , R VI and R VII , R VII and R VIII forms an aromatic ring system fused to the adjacent benzene ring b of formula I, wherein the aromatic ring systems thus formed are identical and optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring a or b and the additional ring or rings formed by adjacent substituents, so formed, fused ring system or systems, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX Each pair of1 which is a direct bond in each case.

[0017] In an even more preferred embodiment of the present invention, exactly one pair of adjacent groups R I and R II , R II and R III , R III and R IV forms an aromatic ring system fused to the adjacent benzene ring a, Exactly one pair of adjacent groups R V and R VI , R VI and R VII , R VII and R VIII forms an aromatic ring system fused to the adjacent benzene ring b of formula I, wherein the fused ring systems thus formed are identical (e.g., both naphthyl) and are optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring a or b and the additional ring or rings formed by adjacent substituents, so formed, fused ring system or systems, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XI and R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and RXVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX is the group Z 1 does not form.

[0018] In a particularly preferred embodiment of the present invention, exactly one pair of adjacent groups R I and R II , R II and R III , R III and R IV forms an aromatic ring system fused to the adjacent benzene ring a, Exactly one pair of adjacent groups R V and R VI , R VI and R VII , R VII and R VIII forms an aromatic ring system fused to the adjacent benzene ring b of formula I, wherein the fused ring systems thus formed are identical (e.g., both naphthyl) and are optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; wherein each benzene ring a or b and the additional ring or rings formed by adjacent substituents, so formed, fused ring system or systems, each contain or consist of a total of 9 to 30 ring atoms, all of which are carbon atoms; where each pair of adjacent groups R IX and R X , R X and R XI , R XIand R XII , R XII and R XIII , R XIV and R XV , R XV and R XVI , R XVI and R XVII , R XVII and R XVIII does not form an aromatic ring system fused to the adjacent benzene rings c or d of formula I, where R I and R XVIII Not only R VIII and R IX is the group Z 1 does not form.

[0019] In one embodiment of the present invention, R A , R B , R X and R 1 From R 8 are independently selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C3-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl), where R 2 and R 3 Not only R X and R 7 Optionally, one pair selected from the group Z 2 which in each occurrence are independently selected from the group consisting of: CR 12 R 13 , C=O, NR 12 , O, SiR 12 R 13 and S. wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 are fused to the adjacent benzene rings e or f of formula II to form an aromatic or aliphatic, carbocyclic or heterocyclic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr,t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring e or f and any fused ring system or systems thus formed, composed of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0020] In a preferred embodiment of the present invention, R A , R B , R X and R 1 From R 8 are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; and N(Ph)2, where R 2 and R 3 Not only R X and R 7 Optionally, one pair selected from the group Z 2 which in each occurrence are independently selected from the group consisting of: CR 12 R 13 , C=O, NR 12 , O, SiR 12 R 13 and S. wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R6 and R 7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 are fused to the adjacent benzene rings e or f of formula II to form an aromatic or aliphatic, carbocyclic or heterocyclic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; wherein each benzene ring e or f and any fused ring system or systems thus formed, composed of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0021] In a more preferred embodiment of the present invention, R A , R B , R X and R 1 From R 8 are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; where R 2 and R 3 Not only R Xand R 7 Optionally, one pair selected from the group Z 2 which in each occurrence are independently selected from the group consisting of: CR 12 R 13 , C=O, NR 12 , O, SiR 12 R 13 and S. wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 are fused to the adjacent benzene rings e or f of formula II to form an aromatic or aliphatic, carbocyclic or heterocyclic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, and CF; wherein each benzene ring e or f and any fused ring system or systems thus formed, consisting of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0022] In an even more preferred embodiment of the present invention, R A , R B , R X and R 1 From R 8 are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; where R 2 and R 3 Not only R X and R 7 Optionally, one pair selected from the group Z 2 which in each occurrence are independently selected from the group consisting of: CR 12 R 13 , N.R. 12 , O and S, wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 are fused to the adjacent benzene rings e or f of formula II to form an aromatic or aliphatic, carbocyclic or heterocyclic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, tBu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, and CF; wherein each benzene ring e or f and any fused ring system or systems thus formed, consisting of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0023] In a further preferred embodiment of the present invention, R A , R B , R X and R 1 From R 8 are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; where R 2 and R 3 Not only R X and R 7 Optionally, one pair selected from the group Z 2 which in each occurrence are independently selected from the group consisting of: CR 12 R 13 , N.R. 12 and O, wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 are fused to the adjacent benzene rings e or f of formula II to form an aromatic or aliphatic, carbocyclic or heterocyclic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu, CN, CF3 and Ph, wherein each benzene ring e or f and any fused ring system or systems thus formed, consisting of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0024] In a particularly preferred embodiment of the present invention, R A , R B , R X and R 1 From R 8 are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; where R 2 and R 3 Not only R X and R 7 Optionally, one pair selected from the group Z 2 which in each occurrence are independently selected from the group consisting of: CR 12 R 13, N.R. 12 and O, wherein optionally, one or more pairs of adjacent groups R 1 and R 2 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 2 and R 8 , R 8 and R X , R X and R B , R B and R A , R A and R 1 are fused to the adjacent benzene rings e or f of formula II to form an aromatic or aliphatic, carbocyclic or heterocyclic ring system optionally substituted with one or more substituents independently selected from the group consisting of: Deuterium, Me, i Pr, t Bu and Ph, wherein each benzene ring e or f and any fused ring system or systems thus formed, consisting of the additional ring or rings formed by adjacent substituents, each contain or consist of a total of 9 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0025] In one embodiment of the present invention, R 12 and R 13 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, CN, CF, or F; C6-C optionally substituted with one or more C1-C5 alkyl substituents 18 aryl, C3-C optionally substituted with one or more C1-C5 alkyl substituents 17 heteroaryl, N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl), where, optionally, R 12 and R 13 two substituents selected from form an aliphatic or aromatic, carbocyclic or heterocyclic ring system containing from 5 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0026] In a preferred embodiment of the present invention, R 12 and R 13 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, Deuterium, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; and N(Ph)2, where, optionally, R 12 and R 13 two substituents selected from form an aliphatic or aromatic, carbocyclic or heterocyclic ring system containing from 5 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms independently selected from N, O and S.

[0027] In a more preferred embodiment of the present invention, R 12 and R 13 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; where, optionally, R 12 and R 13 Two substituents selected from form an aliphatic or aromatic carbocyclic ring system containing from 5 to 30 ring atoms.

[0028] In an even more preferred embodiment of the present invention, R 12 and R 13 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; where, optionally, R 12 and R 13 Two substituents selected from form an aliphatic or aromatic carbocyclic ring system containing from 5 to 30 ring atoms.

[0029] In a particularly preferred embodiment of the present invention, R 12 and R 13 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu and Ph, where, optionally, R 12 and R 13 Two substituents selected from form an aliphatic or aromatic carbocyclic ring system containing from 5 to 30 ring atoms.

[0030] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw, Ix, or Iy; [ka] ...Chemical formula Ia [ka] ...Chemical formula Ib [ka] ...Chemical formula Ic [ka] ...Chemical formula Id [ka] ...Chemical formula Ie [ka] ···Chemical formula If

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[0031] In a preferred embodiment of the invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw, Ix, or Iy, wherein R 9 is hydrogen or deuterium in each case.

[0032] In one embodiment of the invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Ib, Id, Ie, If, Ii, Ij, Ik, Im, In, Io, Iq, Ir, Is, Iv, Iw, Ix, or Iy.

[0033] In a preferred embodiment of the invention, the first chemical moiety comprises or consists of a structure according to formula Ia, Ib, Id, Ie, If, Ii, Ij, Ik, Im, In, Io, Iq, Ir, Is, Iv, Iw, Ix, or Iy, wherein R 9 is hydrogen or deuterium in each case.

[0034] In a more preferred embodiment of the present invention, the first chemical moiety comprises or consists of a structure according to formula Ia, Id, If, In, Iq, or Is.

[0035] In an even more preferred embodiment of the present invention, the first chemical moiety comprises or consists of a structure according to formula Ia, Id, If, In, Iq, or Is, wherein R 9 is hydrogen or deuterium in each case.

[0036] In a further preferred embodiment of the present invention, the first chemical moiety comprises or consists of a structure according to formula Ia or In.

[0037] In particularly preferred embodiments of the present invention, the first chemical moiety comprises or consists of a structure according to formula Ia or In, where R 9 is hydrogen or deuterium in each case.

[0038] In one embodiment of the present invention, the second chemical moiety comprises or consists of a structure according to formula II-a or II-b: [ka] ...Chemical formula II-a [ka] ...Chemical formula II-b Here, the above definitions apply.

[0039] In one embodiment of the present invention, the second chemical moiety comprises or consists of a structure according to formula II-a, where the above definitions apply.

[0040] In one embodiment of the present invention, the second chemical moiety comprises or consists of a structure according to formula II-b, where the above definitions apply.

[0041] In a preferred embodiment of the invention, the second chemical moiety comprises or consists of a structure according to any one of chemical formulas II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-6, II-b-7, II-b-8, II-b-9, II-b-10, II-b-11, II-b-12 and II-b-13; [ka] ...Chemical formula II-a-1 [ka] ...Chemical formula II-a-2

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[0042] In a more preferred embodiment of the invention, the second chemical moiety comprises or consists of a structure according to any one of chemical formulas II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-6, II-b-7, II-b-8, II-b-9, II-b-10, II-b-11, II-b-12, and II-b-13; where: X 1 is C(R 17 )2, NR 15 , O and S; R 15 , R 16 and R 17 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF3, and Deuterium, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; where two or more adjacent groups R 16 optionally forms an aliphatic or aromatic, carbocyclic or heterocyclic ring system fused to a structure according to formula II-a-4, II-a-5, II-a-6 or II-a-7, wherein the entire second chemical moiety according to formula II-a-4, II-a-5, II-a-6 or II-a-7, including the additional ring or rings formed by adjacent substituents, contains 16 to 30 ring atoms, of which 1 to 3 atoms are also heteroatoms selected independently from N, O and S; wherein optionally two substituents R 17 forms an aliphatic or aromatic carbocyclic ring system containing from 5 to 30 carbon atoms.

[0043] In one embodiment of the invention, the second chemical moiety comprises or consists of a structure according to any of chemical formulas II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-9 and II-b-10, wherein the foregoing definitions apply.

[0044] In a preferred embodiment of the invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Ib, Ic, Id, Ie, If, Ig, Ih, Ii, Ij, Ik, Im, In, Io, Ip, Iq, Ir, Is, It, Iu, Iv, Iw, Ix or Iy, to which the above definitions apply, and the second chemical moiety comprises or consists of a structure according to chemical formula II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-6, II-b-7, II-b-8, II-b-9, II-b-10, II-b-11, II-b-12 or II-b-13, to which the above definitions apply.

[0045] In a more preferred embodiment of the invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Ib, Id, Ie, If, Ii, Ij, Ik, Im, In, Io, Iq, Ir, Is, Iv, Iw, Ix or Iy, to which the foregoing definitions apply, and the second chemical moiety comprises or consists of a structure according to chemical formula II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-6, II-b-7, II-b-8, II-b-9, II-b-10, II-b-11, II-b-12 or II-b-13, to which the foregoing definitions apply.

[0046] In an even more preferred embodiment of the present invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Id, If, In, Iq or Is, to which the above definitions apply, and the second chemical moiety comprises or consists of a structure according to chemical formula II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-6, II-b-7, II-b-8, II-b-9, II-b-10, II-b-11, II-b-12 or II-b-13, to which the above definitions apply.

[0047] In a further preferred embodiment of the invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia, Id, If, In, Iq or Is, to which the above definitions apply, and the second chemical moiety comprises or consists of a structure according to chemical formula II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-9 and II-b-10, to which the above definitions apply.

[0048] In particularly preferred embodiments of the present invention, the first chemical moiety comprises or consists of a structure according to chemical formula Ia or In, to which the above definitions apply, and the second chemical moiety comprises or consists of a structure according to chemical formula II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6, II-a-7, II-b-1, II-b-2, II-b-3, II-b-4, II-b-5, II-b-9 and II-b-10, to which the above definitions apply.

[0049] As used throughout this specification, the term "cyclic group" is understood in the broadest sense to refer to any monocyclic, bicyclic or polycyclic moiety.

[0050] As used throughout this specification, the terms "ring" and "ring system" are to be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0051] The term "ring atom" refers to any atom that is part of the cyclic core of a ring or ring structure and that is not part of an optional substituent attached thereto.

[0052] As used throughout this specification, the term "carbocycle" is understood in its broadest sense as any cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen or any other substituent as defined in specific embodiments of this invention. The term "carbocyclic" is also understood as an adjective, referring to a cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen or any other substituent as defined in specific embodiments of this invention.

[0053] As used throughout this specification, the term "heterocycle" is understood in the broadest sense as any cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The term "heterocyclic" is also understood as an adjective and refers to a cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The heteroatoms may be the same or different in each case and may be individually selected from the group consisting of N, O, and S, unless otherwise specified in a specific embodiment. In the context of the present invention, all carbon atoms or heteroatoms contained in a heterocycle may, of course, be substituted with hydrogen or any other substituent defined in a specific embodiment of the present invention.

[0054] As used throughout this specification, the term "aromatic ring system" is also understood in its broadest sense as any bicyclic or polycyclic aromatic moiety.

[0055] As used throughout this specification, the term "heteroaromatic ring system" is also understood in its broadest sense as any bicyclic or polycyclic heteroaromatic moiety.

[0056] As used throughout this specification, when referring to an aromatic or heteroaromatic ring system, the term "fused" means that the "fused" aromatic or heteroaromatic rings share at least one bond that is part of both ring systems. For example, naphthalene (or naphthyl, when referred to as a substituent) or benzothiophene (or benzothiophenyl, when referred to as a substituent) is considered a fused aromatic ring system in the context of this invention, where the two benzene rings (in the case of naphthalene) or thiophene and benzene (in the case of benzothiophene) share one bond. Sharing a bond in this context is also understood to include sharing the two atoms that make up each bond, and a fused aromatic or heteroaromatic ring system is also understood to be a single aromatic or heteroaromatic system. It is also understood that one or more bonds are shared by the aromatic or heteroaromatic rings that make up a fused aromatic or heteroaromatic ring system (e.g., pyrene). Aliphatic ring systems may also be fused, which will be understood to have the same meaning as aromatic or heteroaromatic ring systems, except that fused aliphatic ring systems are not aromatic.

[0057] As used throughout this specification, the terms "aryl" and "aromatic" are understood in the broadest sense to refer to any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms. A heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this specification, the number of aromatic ring atoms may be given in subscript numerals in the definitions of certain substituents. In particular, heteroaromatic rings contain 1 to 3 heteroatoms. Furthermore, the terms "heteroaryl" and "heteroaromatic" are understood in the broadest sense to refer to any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom, which in each case may be the same or different and may be independently selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent that possesses two binding sites and serves as a linker structure for other molecular structures. In exemplary embodiments, if a group is defined differently from the definitions given herein, for example, if the number of aromatic ring atoms or heteroatoms differs from the definitions given, the definition in the exemplary embodiment applies. According to the present invention, a fused (annulated) aromatic or heteroaromatic polycycle is composed of two or more single aromatic or heteroaromatic rings that form the polycycle via a condensation reaction.

[0058] In particular, as used throughout this specification, the term "aryl group" or "heteroaryl group" refers to any of the following: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, 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, naphthoimidazole, phenanthridine, pyridoimidazole ... and benzothiadiazole, 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 group that can be attached through any position of an aromatic or heteroaromatic group derived from a benzothiadiazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, 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 aforementioned groups.

[0059] As used throughout this specification, the term "adjacent substituents" or "adjacent groups" means substituents or groups that are attached to the same or adjacent atoms.

[0060] As used throughout this specification, the term "aliphatic" when referring to a ring system is also understood in its broadest sense to mean that none of the rings comprising the ring system are aromatic or heteroaromatic. Such aliphatic ring systems are also understood to be fused to one or more aromatic rings, such that some, but not all, of the carbon atoms or heteroatoms contained in the core structure of the aliphatic ring system are part of the aromatic ring to which they are attached.

[0061] As used throughout this specification, the term "alkyl group" is understood in its broadest sense to refer to any linear, branched, or cyclic alkyl substituent. In particular, the term "alkyl" refers to the substituents methyl (Me), ethyl (Et), n-propyl (N-propyl), ... n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-butyl ( i Bu), s-butyl ( s Bu), t-butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, 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-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n- 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadece-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec- 1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadece-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

[0062] As used throughout this specification, the term "alkenyl" includes linear, branched, and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0063] As used throughout this specification, the term "alkynyl" includes linear, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0064] As used throughout this specification, the term "alkoxy" includes linear, branched, and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.

[0065] The term "thioalkoxy," as used throughout, includes linear, branched, and cyclic thioalkoxy substituents, where O in the exemplary alkoxy group is replaced with S.

[0066] The terms "halogen" and "halo" as used throughout this specification are also understood in the broadest sense to preferably mean fluorine, chlorine, bromine or iodine.

[0067] When a molecular fragment is described as being attached to a substituent or other moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the entire molecule (e.g., naphthalene, dibenzofuran). As used herein, the above modes of describing a substituent or attached fragment are considered equivalent.

[0068] All hydrogen atoms (H) contained in any structure referred to in this application are also replaced, in each case independently of one another, with deuterium (D), unless specifically stated otherwise. The replacement of hydrogen with deuterium is common practice and will be apparent to those skilled in the art.

[0069] In one embodiment, the organic molecules according to the present invention have an excited-state lifetime of 250 μs or less, 150 μs or less, particularly 100 μs or less, more preferably 80 μs or less, or 60 μs or less, and even more preferably 40 μs or less in a poly(methyl methacrylate) (PMMA) film containing 2 wt % of the organic molecules at room temperature (i.e., about 25° C.).

[0070] In one embodiment of the present invention, the organic molecule according to the present invention exhibits a thermally activated delayed fluorescence (TADF) emitter, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), ΔE ST value, which is 5000 cm -1 less than, preferably, 3000 cm -1 less than, more preferably, 1500 cm -1 less than, even more preferably, 1000 cm -1 Less than or equal to 500cm -1 Indicates less than.

[0071] In a further embodiment of the present invention, the organic molecules according to the present invention have an emission peak in the visible or near-ultraviolet range, i.e., in the wavelength range of 420 nm to 580 nm, in a PMMA (poly(methyl methacrylate)) film containing 2% by weight of the organic molecules at room temperature (i.e., about 25° C.), with a full width at half maximum value of less than 0.30 eV, preferably less than 0.28 eV, more preferably less than 0.23 eV, or even less than 0.20 eV.

[0072] Orbital energies and excited state energies can be determined through experimental methods and computational methods using quantum chemical methods, particularly density functional theory calculations. The highest occupied molecular orbital energy, E HOMO is determined to an accuracy of 0.1 eV from cyclic voltammetry measurements by methods known to those skilled in the art. LUMO is determined as the onset of the absorption spectrum.

[0073] The onset of the absorption spectrum is determined by calculating the intersection of a tangent to the absorption spectrum with the x-axis, which is set at the low energy side of the absorption band and at half maximum intensity of the absorption spectrum.

[0074] Unless otherwise stated, the energy of the first excited triplet state T1 is determined from the onset of the phosphorescence spectrum (normal state spectrum, PMMA film containing 2 wt. % of emitter) at 77 K.

[0075] Unless otherwise stated, the energy of the first excited singlet state S1 is determined from the onset of the fluorescence spectrum at room temperature (ie, about 25° C., normal state spectrum, PMMA film containing 2 wt % of emitter).

[0076] The onset of the emission spectrum is determined by calculating the intersection of a tangent to the emission spectrum with the x-axis, which is set at the high energy side of the emission band and the half maximum intensity point of the emission spectrum.

[0077] ΔE corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) ST The values ​​are determined based on the first excited singlet state energy and the first excited triplet state energy, which are determined as described above.

[0078] A further aspect of the present invention relates to the use of organic molecules according to the present invention as light emitters or absorbers and / or host materials and / or electron transport materials and / or hole injection materials and / or hole blocking materials in optoelectronic devices.

[0079] An optoelectronic device is understood in the broadest sense as any device using organic materials that is suitable for emitting light in the visible or near ultraviolet (UV) range, i.e., in the wavelength range from 380 to 800 nm. More preferably, the optoelectronic device is capable of emitting light in the visible range, i.e., from 400 to 800 nm.

[0080] In connection with such applications, the optoelectronic device is more particularly selected from the group consisting of: -Organic Light Emitting Diode (OLED) -Light-emitting electrochemical cells -OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside -Organic diode -Organic solar cells -Organic transistor -Organic field-effect transistors -Organic laser -Down conversion element.

[0081] The light-emitting electrochemical cell comprises three layers: a cathode, an anode, and an active layer comprising organic molecules according to the present invention.

[0082] For such applications, in preferred embodiments, 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.

[0083] In one embodiment, the light-emitting layer of an organic light-emitting diode comprises organic molecules according to the present invention.

[0084] In one embodiment, the light-emitting layer of the organic light-emitting diode includes not only the organic molecule according to the present 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.

[0085] A further aspect of the present invention relates to a composition comprising or consisting of: (a) organic molecules according to the invention, in particular in emitter and / or host form, (b) one or more emitter and / or host materials different from the organic molecules according to the invention, and (c) optionally, one or more dyes and / or one or more solvents.

[0086] In one embodiment, the light-emitting layer comprises (or consists essentially of) a composition comprising or consisting of: (a) at least one organic molecule according to the invention, in particular in emitter and / or host form, (b) one or more emitter and / or host materials different from the organic molecules according to the invention, and (c) optionally, one or more dyes and / or one or more solvents.

[0087] In further embodiments of the present invention, the composition has a photoluminescence quantum yield (PLQY) at room temperature of greater than 10%, preferably greater than 20%, more preferably greater than 40%, even more preferably greater than 60% or even greater than 70%.

[0088] In particular embodiments, the emissive layer EML comprises (or consists essentially of) a composition comprising or consisting of: (i) 0.1 to 10% by weight, preferably 0.5 to 5% by weight, in particular 1 to 3% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight, of at least one host compound H, (iii) 0.9 to 94.9% by weight, preferably 14.5 to 80% by weight, in particular 24 to 77% by weight, of one or more additional host compounds D having a structure different from that of the molecules according to the invention, (iv) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent, and (v) optionally 0 to 30% by weight, in particular 0 to 20% by weight, preferably 0 to 5% by weight, of one or more additional emitter molecules F having a structure different from that of the molecules according to the invention.

[0089] Preferably, energy can be transferred from the host compound H to one or more organic molecules according to the invention, in particular 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 organic molecules according to the invention 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 organic molecules according to the invention.

[0090] In one embodiment, the host compound H has an energy E in the range of −5 to −6.5 eV. HOMO (H), and one organic molecule E according to the present invention has a highest occupied molecular orbital HOMO (H) with energy E HOMO (E) has the highest occupied molecular orbital HOMO (E), where E HOMO (H)>E HOMO (E).

[0091] In a further embodiment, the host compound H has an energy E LUMO (H), and one organic molecule E according to the present invention has a lowest unoccupied molecular orbital (LUMO) with energy E LUMO (E) has a lowest unoccupied molecular orbital (LUMO) (E), where E LUMO (H)>E LUMO (E).

[0092] In one embodiment of the organic light-emitting diode according to the invention, the host compound H has an energy E HOMO (H), and at least one additional host compound D has a highest occupied molecular orbital HOMO (H) with energy E HOMO (D) has the highest occupied molecular orbital HOMO (D), where E HOMO (H)>E HOMO (D). E HOMO (H)>E HOMO (D) The relationship favors efficient hole transport.

[0093] In a further embodiment, the host compound H has an energy E LUMO(H), and at least one additional host compound D has a lowest unoccupied molecular orbital LUMO (H) with energy E LUMO (D) has a lowest unoccupied molecular orbital (LUMO) (D), where E LUMO (H)>E LUMO (D). E LUMO (H)>E LUMO (D) The relationship favors efficient electron transport.

[0094] In one embodiment of the organic light-emitting diode according to the invention, the host compound H has an energy E HOMO (H) with the highest occupied molecular orbital HOMO (H), and energy E LUMO (H) having a lowest unoccupied molecular orbital (LUMO) (H), At least one additional host compound D has an energy E HOMO (D) has the highest occupied molecular orbital HOMO(D), and energy E LUMO (D) has a lowest unoccupied molecular orbital (LUMO) (D), The organic molecule E according to the present invention has an energy E HOMO The highest occupied molecular orbital (HOMO) with (E), and energy E LUMO (E) having a lowest unoccupied molecular orbital (LUMO) (E), where: E HOMO (H)>E HOMO (D), and the energy level of the highest occupied molecular orbital (HOMO) (E) of the organic molecule E according to the present invention (E HOMO (E)) and the energy level of the highest occupied molecular orbital (HOMO) of the host compound H (E HOMO (H)) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV, or -0.1 eV to 0.1 eV; E LUMO (H)>E LUMO (D), and the energy level of the lowest unoccupied molecular orbital (LUMO) (E) of the organic molecule E according to the present invention (E LUMO (E)) and the energy level of the lowest unoccupied molecular orbital (LUMO) (D) of at least one additional host compound D (E LUMOThe difference from (D)) is -0.5 eV to 0.5 eV, more preferably -0.3 eV to 0.3 eV, even more preferably -0.2 eV to 0.2 eV, or -0.1 eV to 0.1 eV.

[0095] In one embodiment of the present invention, the host compound D and / or the host compound H is a thermally activated delayed fluorescence (TADF) material. The TADF material has a wavelength of 2500 cm -1 ΔE, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), is less than ST Preferably, the TADF material has a luminance of 3000 cm -1 less than, more preferably, 1500 cm -1 less than, even more preferably, 1000 cm -1 Less than or equal to 500 cm -1 Less than ΔE ST Indicates the value.

[0096] In one embodiment, host compound D is a TADF material and host compound H is a TADF material having a wavelength of 2500 cm -1 Larger ΔE ST In certain embodiments, the host compound D is a TADF material and the host compound H is selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 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-dibenzothiophenyl)phenyl]-9H-carbazole.

[0097] In one embodiment, the host compound H is a TADF material and the host compound D is a TADF material having a luminescence wavelength of 2500 cm -1 Larger ΔE STIn a particular embodiment, the host compound H is a TADF material and the host compound D is selected from the group consisting of 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST).

[0098] optoelectronic devices In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition as described herein, more particularly a device selected from the group consisting of organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, in particular gas and vapor sensors that are not completely sealed off from the outside world, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and down conversion devices.

[0099] 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.

[0100] In one embodiment of the optoelectronic device of the present invention, the organic molecules according to the present invention are used as emissive material in the emissive layer EML.

[0101] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML is composed of the composition according to the present invention as described herein.

[0102] When the optoelectronic device is an OLED, it can have, for example, the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer Here, the OLED may optionally include each layer, different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0103] The optoelectronic device, in one embodiment, also includes one or more protective layers that protect the device from damaging exposure to harmful substances in the environment, including, for example, moisture, vapors and / or gases.

[0104] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Emitting layer B 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A Here, an OLED having an inverted layer structure may optionally include each layer, and different layers may be combined, and the OLED may also include one or more layers of each layer type defined above.

[0105] In one embodiment of the present invention, the optoelectronic device is an OLED that can have a stacked structure. In this structure, individual units are stacked on top of each other, unlike the common arrangement in which OLEDs are arranged side by side. Mixed light is generated by an OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED, and a red OLED. An OLED that exhibits a stacked structure may also include a charge generation layer (CGL), which is typically located between two OLED subunits and typically configured as an n-doped layer and a p-doped layer. Typically, the n-doped layer of one CGL is located closer to the anode layer.

[0106] In one embodiment of the present invention, the optoelectronic device is an OLED comprising two or more light-emitting layers between an anode and a cathode. In particular, a so-called tandem OLED comprises three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and may optionally comprise additional layers, such as a charge generation layer, a charge blocking layer, or a charge transport layer, between each of the light-emitting layers. In a further embodiment, the light-emitting layers are stacked adjacently. In a further embodiment, the tandem OLED comprises a charge generation layer between each of the two light-emitting layers. Adjacent light-emitting layers or light-emitting layers separated by a charge generation layer may also be combined.

[0107] The substrate can be made of any material or composition of materials. Most often, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver, or aluminum film) or a plastic film or slide can be used, which allows for a higher level of flexibility. The anode layer A is made of a material that allows for a nearly (essentially) transparent film. To allow light emission from the OLED, at least one of the two electrodes must be (essentially) transparent, so either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or made of transparent conductive oxides (TCOs). Such anode layers A may, for example, comprise 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.

[0108] Preferably, the anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO3) 0.9 (SnO2) 0.1). The roughness of the anode layer A due to the transparent conductive oxide (TCO) can also be reduced by using a hole injection layer (HIL). The HIL also facilitates the injection of like charge carriers (i.e., holes) in that the transport of like charge carriers from the TCO to the hole transport layer (HTL) is promoted. The hole injection layer (HIL) can also include poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO2, VO5, CuPC, or CuI, particularly a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent metal diffusion from the anode layer A to the hole transport layer (HTL). For example, the HIL may be poly-3,4-ethylenedioxythiophene:polystyrenesulfonic acid (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene (Spiro-TAD), N1,N1′-(biphenyl-4,4′-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N′-bis(1-naphthyl)-(2 ... It may also be composed of N,N'-triphenyl-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0109] The hole transport layer (HTL) is generally located adjacent to the anode layer A or the hole injection layer (HIL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can also 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 function as an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) may be formed of tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′,4″-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or 9,9′-diphenyl-6-(9-phenyl-9H- The HTL may also include a star-shaped heterocycle such as (carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer composed of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopant may be, for example, a transition metal oxide such as vanadium oxide, molybdenum oxide, or tungsten oxide. The organic dopant may be, for example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz), or a transition metal complex.

[0110] EBLs may also include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0111] The light-emitting layer (EML) is typically located adjacent to the hole-transporting layer (HTL). The light-emitting layer (EML) comprises at least one light-emitting molecule. In particular, the EML comprises at least one light-emitting molecule according to the present invention. In one embodiment, the light-emitting layer comprises only organic molecules according to the present invention. Typically, the EML further comprises one or more host materials H. For example, the host material H may be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), mCP, mCBP, dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), CzSi, dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenz ...

[0033] The compound is selected from the group consisting of 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). The host material H should generally be selected to exhibit a first triplet (T1) energy level and a first singlet (S1) energy level that are energetically higher than the first triplet (T1) energy level and the first singlet (S1) energy level of the organic molecule.

[0112] In one embodiment of the present invention, the EML comprises a so-called mixed host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one light-emitting organic molecule according to the present invention, T2T as the electron-dominant host, and one selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 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-dibenzothiophenyl)phenyl]-9H-carbazole as the hole-dominant host. In a further embodiment, the EML comprises 50 to 80% by weight, preferably 60 to 75% by weight, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 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-dibenzothiophenyl)phenyl]-9H-carbazole, 10 to 45% by weight, preferably 15 to 30% by weight, of T2T, and 5 to 40% by weight, preferably 10 to 30% by weight, of an emissive molecule according to the present invention.

[0113] An electron transport layer (ETL) may be located adjacent to the light-emitting layer (EML). Any electron transporter may be used here. For example, electron-deficient 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-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may also include 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum tris(8-hydroxyquinoline) (Alq), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO), 2,7-di(2,2′-bipyridin-5-yl)triphenyl (BPyTP), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or 4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl (BTB). Optionally, the ETL is also doped with a material such as Liq. The electron transporting layer (ETL) can also block holes, or a hole blocking layer (HBL) is introduced.

[0114] Examples of HBL include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine (BCP), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq), diphenyl-4-triphenylsilylphenyl-phosphine oxide, and the like. These include 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST) and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0115] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively, or in addition, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscale silver wires.

[0116] The OLED optionally further comprises a protective layer (also referred to as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The layer may comprise lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li2O, BaF2, MgO, and / or NaF.

[0117] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds.

[0118] The emitting layer EML may further include one or more additional emitter molecules F to further modify the emission and / or absorption spectrum of the emitting layer EML. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F are molecules having a structure different from that of the molecules according to the present invention. The emitter molecules F may also be TADF emitters. Alternatively, the emitter molecules F may be fluorescent and / or phosphorescent emitter molecules capable of shifting the emission and / or absorption spectrum of the emitting layer EML. For example, triplet and / or singlet excitons may be transferred from the organic emitter molecules according to the present invention to the emitter molecules F before relaxing to the ground state S, typically emitting red-shifted light compared to the light emitted by the emitter molecules F. Optionally, the emitter molecules F may also induce a two-photon effect (i.e., absorption of two photons at half the maximum absorption energy).

[0119] Optionally, the optoelectronic device (e.g., OLED) can also be, for example, an essentially 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. Optionally, there can then be energy transfer between the two or more molecules, as described above.

[0120] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: wavelength range of >380~420nm Deep blue: wavelength range of >420~480nm Sky blue: wavelength range of >480~500nm Green: wavelength range of >500~560nm Yellow: wavelength range of >560-580nm Orange: wavelength range of >580~620nm Red: wavelength range of >620~800nm

[0121] Associated with the emitter molecule, such hues exhibit emission maxima. Thus, for example, a deep blue emitter has an emission maximum in the >420-480 nm range, a sky blue emitter has an emission maximum in the >480-500 nm range, a green emitter has an emission maximum in the >500-560 nm range, and a red emitter has an emission maximum in the >620-800 nm range.

[0122] A further aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates that are close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of primary blue (CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, such as UHD-TVs. Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, even more preferably 0.08 to 0.18, or even 0.10 to 0.15, and / or CIEy color coordinates of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, even more preferably 0.03 to 0.15, or even 0.04 to 0.10.

[0123] A further embodiment of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD displays, e.g., UHD-TVs. In this context, the term "close" refers to the range of CIEx and CIEy coordinates provided at the end of the paragraph. While commercial applications typically use top-emitting devices (where the top electrode is transparent), the test devices used throughout this invention represent bottom-emitting devices (where the bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates of 0.15 to 0.45, preferably 0.15 to 0.35, more preferably 0.15 to 0.30, even more preferably 0.15 to 0.25 or even 0.15 to 0.20, and / or CIEy color coordinates of 0.60 to 0.92, preferably 0.65 to 0.90, more preferably 0.70 to 0.88, even more preferably 0.75 to 0.86 or even 0.79 to 0.84.

[0124] A further embodiment of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.708) and CIEy (=0.292) color coordinates of primary red (CIEx=0.708 and CIEy=0.292) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD displays, e.g., UHD-TVs. In this context, the term "close" refers to the range of CIEx and CIEy coordinates provided at the end of the paragraph. While commercial applications typically use top-emitting devices (where the top electrode is transparent), the test devices used throughout this invention represent bottom-emitting devices (where the bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates of 0.60 to 0.88, preferably 0.61 to 0.83, more preferably 0.63 to 0.78, even more preferably 0.66 to 0.76 or even 0.68 to 0.73, and / or CIEy color coordinates of 0.25 to 0.70, preferably 0.26 to 0.55, more preferably 0.27 to 0.45, even more preferably 0.28 to 0.40 or even 0.29 to 0.35.

[0125] Therefore, a further aspect of the present invention is a method for manufacturing a 14500 cd / m 2 and / or an OLED having an emission maximum at 420 nm to 580 nm, preferably at 440 nm to 560 nm, more preferably at 470 nm to 550 nm, particularly preferably at 500 nm to 540 nm; and / or an LT97 value at 14500 cd / m2 of more than 100 h, preferably more than 250 h, more preferably more than 500 h, even more preferably more than 750 h, or even more than 1000 h.

[0126] The optoelectronic device, in particular the OLED according to the present invention, may be fabricated by any means of vapor deposition and / or liquid processes. Thus, at least one layer may be - produced by a sublimation process, - prepared by organic vapor phase deposition process; - produced by a carrier gas sublimation process, solution processing, or -Printed.

[0127] The methods used to fabricate optoelectronic devices, and in particular OLEDs according to the present invention, are known in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition steps. The individual layers may be deposited using the same or different deposition methods.

[0128] For example, vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. In the case of active matrix OLED displays, an AMOLED backplane is used as the substrate. Individual layers can also be processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., a nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art. [Example]

[0129] General synthesis method The general synthetic scheme provides a synthetic scheme for organic molecules according to the present invention. [ka] [ka]

[0130] General procedure for synthesis: Step 1 Under a nitrogen atmosphere, a two-neck flask was charged with 1,3-dibromo-5-chlorobenzene [81067-41-6] (1.0 equiv.), arylamine E1 (2.2 equiv.), Pd(dba) [51364-51-3] (0.01 equiv.), and sodium tert-butoxide [865-48-5] (4.0 equiv.). Dry toluene (5 mL / mmol of 1,3-dibromo-5-chlorobenzene) and tri-tert-butylphosphine [13716-12-6] (0.08 equiv.) were added, and the resulting suspension was degassed (by bubbling nitrogen) for 10 min. The mixture was then heated at 90 °C until complete (typically 10–16 h). After cooling to room temperature (rt), water is added, the phases are separated, the aqueous layer is extracted with ethyl acetate, and the combined organic layers are dried over MgSO, filtered, and concentrated. The crude product is purified by column chromatography or recrystallization to give the corresponding product P1 as a solid.

[0131] Step 2 Under a N2 atmosphere, a two-neck flask is charged with P1 (1.0 equiv.), aryl bromide E2 (2.2 equiv.), Pd2(dba)3 [51364-51-3] (0.02 equiv.), and sodium tert-butoxide [865-48-5] (2.3 equiv.). Dry toluene (16 mL / mmol of P1) and tri-tert-butylphosphine [131274-22-1] (0.08 equiv.) are added, and the resulting suspension is degassed (nitrogen sparged) for 10 min. The mixture is then heated at 110 °C until complete (typically 10-24 h). After cooling to room temperature (rt), water is added, the phases are separated, the aqueous layer is extracted with ethyl acetate, and the combined organic layers are dried over MgSO4, filtered, and concentrated. The crude product is purified by column chromatography or recrystallization to give the corresponding product P2 as a solid.

[0132] Step 3 In a flame-dried two-neck flask under N2 atmosphere, aryl chloride P2 (1.0 equiv.) is dissolved in degassed tert-butylbenzene. At 20 °C, tert-butyllithium solution (1.9 M [594-19-4] (3.3 equiv.) in pentane) is added dropwise. The mixture is then stirred at 40 °C until lithiation is complete (2-3 h). At 0 °C, trimethyl borate [121-43-7] (6.0 equiv.) is slowly added, and stirring is continued at 20 °C until boronation is complete (1-2 h). Water is then added, and the resulting two-phase mixture is stirred at 20 °C for 15 min. Ethyl acetate is added, the phases are separated, and the combined organic layers are dried over MgSO4, filtered, and concentrated. The crude product is purified by recrystallization to give the corresponding boronic acid P3 as a solid.

[0133] Step 4 Under a N2 atmosphere, a two-neck flask is charged with boronic acid P3 (1.0 equiv.). Dry chlorobenzene is added, followed by aluminum chloride [7446-70-0] (10 equiv.) and N,N-diisopropylethylamine (DIPEA) [7087-68-5] (10 equiv.). The resulting mixture is heated at 120 °C until the reaction is complete (1-2 h). After cooling to room temperature, the reaction is quenched with ice water. The phases are then separated, and the aqueous layer is extracted with dichloromethane. The combined organic layers are dried over MgSO4, filtered, and concentrated. The residue is filtered through a silica plug, followed by precipitation with acetonitrile and dichloromethane solution to obtain the desired material P4 as a solid.

[0134] Step 5 Under a N2 atmosphere, a two-neck flask is charged with P4 (1.0 equiv.), bis(pinacolato)diboron [73183-34-3] (5.0 equiv.), Pd2(dba)3 [51364-51-3] (0.02 equiv.), X-Phos [564483-18-7] (0.08 equiv.), and potassium acetate [127-08-2] (7.5 equiv.). Dry dioxane (20 mL / mmol of P4) is added, and the resulting mixture is degassed (nitrogen sparged) for 10 minutes. The mixture is then heated at 100 °C for 24 hours. After cooling to room temperature (rt), dichloromethane and water are added, the phases are separated, and the aqueous layer is extracted with dichloromethane. The combined organic layers are stirred with MgSO4 / Celite® (diatomaceous earth) / charcoal at room temperature for 10 minutes, filtered, and concentrated. The crude product is used in further transformations without purification to give the desired boronic ester P5 as a solid.

[0135] Step 6 Under a N2 atmosphere, a two-neck flask is charged with P5 (1.0 equiv.), heteroaryl bromide E3, E4, or E5 (4.0 equiv.), Pd(PPh3)4 [14221-01-3] (0.1 equiv.), and potassium carbonate [584-08-7] (3.0 equiv.). A mixture of DMF and water (10:1 volume ratio, 60 mL / mmol of P5) is added, and the resulting mixture is degassed (nitrogen sparged) for 15 minutes. The mixture is then heated at 150 °C for 4-6 hours. After cooling to room temperature (rt), the mixture is poured into water. The precipitated solid is filtered and washed with ethanol. The crude product is purified by recrystallization to give the corresponding product M1, M2, or M3 as a solid.

[0136] Cyclic Voltammetry Cyclic voltammograms are performed in dichloromethane, or a suitable solvent, and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) at a concentration of 10 -3The measurement was carried out at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire) and FeCp2 / FeCp2 as an internal standard. + The HOMO data were corrected using ferrocene as an internal standard relative to a saturated calomel electrode (SCE).

[0137] Density functional theory calculations The molecular structures were optimized using the BP86 function and the RI (Resolution of Identity) approach. The excitation energies were calculated with the TD-DFT (Time-Dependent DFT) method using the (BP86) optimized structures. The orbital energies and excited-state energies were calculated using the B3LYP function. The Def2-SVP basis set and m4-grid were used for numerical integration. The Turbomole program package was used for all calculations.

[0138] optical physical measurements Sample pretreatment: spin coating Equipment: Spin150, SPS euro The sample concentration is 0.2 mg / ml dissolved in toluene / DCM. Program: 2000 U / min for 7-30 seconds. After coating, the film was dried at 70°C for 1 minute.

[0139] Absorption measurements A Thermo Scientific Evolution 201 UV-Visible spectrophotometer was used to determine the maximum absorption wavelength of the sample in the wavelength range above 270 nm, which was used as the excitation wavelength for measuring the photoluminescence spectrum and quantum yield.

[0140] Photoluminescence and phosphorescence spectroscopy For phosphorescence and photoluminescence spectroscopy analysis, a Horiba fluorescence spectrometer "Fluoromax 4P" is used.

[0141] Time-resolved PL spectroscopy in the μs and ns range (FS5) Time-resolved PL measurements are performed on an Edinburgh Instruments FS5 fluorescence spectrometer. Compared to measurements on the HORIBA setup, better light collection allows for an optimized signal-to-noise ratio, making the FS5 system particularly advantageous for transient PL measurements of delayed fluorescence properties. As a continuous light source, the spectrometer contains a 150W xenon arc lamp, and the specific wavelength is selected by a Czerny-Turner monochromator. However, standard measurements are instead performed using an external VPLED tunable pulsed LED with an emission wavelength of 310 nm. The sample emission is directed to a highly sensitive R928P photomultiplier tube (PMT), which can detect single photons with a peak quantum efficiency of up to 25% in the spectral range from 200 nm to 870 nm. The detector is a temperature-stabilized PMT providing dark counts below 300 cps (counts per second). Finally, a tail fit using three exponential functions is applied to determine the transient decay lifetime of the delayed fluorescence. Specific lifetime τ i and the corresponding amplitude A i The delayed fluorescence lifetime τ DF is determined.

number

[0142] Photoluminescence quantum yield measurements For photoluminescence quantum yield (PLQY) measurements, an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using software U6039-05 version 3.6.0.

[0143] The emission maxima are given in nm, the quantum yields Φ are given in % and the CIE coordinates are given as x,y values.

[0144] PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard. 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured on a film sample (2 wt % emitter in PMMA) in a nitrogen atmosphere. The yield is calculated using the following equation:

number

[0145] Time-Correlated Single Photon Counting (TCSPC) Excited state distribution dynamics are determined using an Edinburgh Instruments FS5 spectrofluorometer equipped with an emission monochromator, a temperature-stabilized photomultiplier tube as the detector unit, and a pulsed LED (310 nm central wavelength, 910 ps pulse width) as the excitation source. Samples are placed in cuvettes and flushed with nitrogen during measurements.

[0146] Overall damping mechanics The entire excited state population decay dynamics over multiple orders of magnitude in time and signal intensity is achieved by performing TCSPC measurements in four time domains (200 ns, 1 μs, 20 μs, and longer measurement periods >80 μs). The measured time curves are then processed in the following manner. 1. Determine the average signal level before excitation and subtraction and apply background correction. 2. The initial rise of the main signal is taken as the reference and the time axis is aligned. 3. Using the superimposed measured time domains, the curves are scaled relative to each other. 4. The processed curves are merged into one curve.

[0147] Data analysis Data analysis is performed using a single or double exponential fit of the immediate fluorescence (PF) and delayed fluorescence (DF) decays separately. The ratio of delayed to immediate fluorescence (n value) is calculated by integrating each photoluminescence decay over time:

number

[0148] The mean excited state lifetime is calculated by averaging the decay times of the prompt and delayed fluorescence, weighted by the respective contributions of PF and DF.

[0149] Fabrication and characterization of optoelectronic devices Optoelectronic devices, particularly OLED devices, containing the organic molecules according to the present invention can also be prepared by vacuum deposition. When a layer contains one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so if no value is specified, the fraction of the compound is the difference between the specified value and 100%.

[0150] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance; similarly, LT80 corresponds to the time when the measured luminance has decreased to 80% of the initial luminance, and LT97 corresponds to the time when the measured luminance has decreased to 97% of the initial luminance.

[0151] Accelerated lifetime measurements are performed (e.g., applying increasing current densities, e.g., 500 cd / m 2 In the present invention, the LT80 value is determined using the following formula:

number

[0152] The values ​​correspond to the average of multiple pixels (typically 2-8), and the standard deviation across the pixels is provided. The figures show data series for one OLED pixel.

[0153] HPLC-MS HPLC-MS analysis is carried out on an Agilent HPLC-MS (HPLC1260 Infinity) equipped with an MS detector (Single Quadrupole).

[0154] For example, a typical HPLC method is as follows: A reverse phase column 3.0 mm x 100 mm and particle size 2.7 μm from Agilent (Poroshell 120EC-C18, 3.0 x 100 mm, 2.7 μm HPLC column) is used for HPLC. HPLC-MS measurements are performed at 45°C with the following gradient: [Table 1] The following solvent mixtures were also used (all solvents contained 0.1% (V / V) formic acid): [Table 2]

[0155] From the analyte solution at a concentration of 0.5 mg / mL, an injection volume of 2 μL is taken for the measurement. Ionization of the probe is performed in an APCI (atmospheric pressure chemical ionization) source using positive (APCI+) or negative (APCI-) ionization mode, or using an APPI (atmospheric pressure photoionization) source.

[0156] Example 1 [ka] Example 1 is synthesized by: Procedure 1 (78% yield), in which 3,5-di-tert-butylaniline [2380-36-1] was used as compound E1, Step 2 (59% yield), Step 3 (27% yield), Step 4 (59% yield), Step 5 (quantitative yield), Procedure 6 (30% yield), where 2-bromobiphenyl [92-66-0] is used as compound E3. MS (HPLC-MS): m / z (residence time) = 898.0 (8.42 minutes). Example 1 has an emission maximum (2 wt % in PMMA) of 474 nm, a full width at half maximum (FWHM) of 0.13 eV (23 nm), CIEx and CIEy coordinates of 0.12 and 0.22, respectively, and a PLQY of 64%.

[0157] Example 2 [ka]

[0158] Example 2 is synthesized by: Procedure 1 (78% yield), in which 3,5-di-tert-butylaniline [2380-36-1] was used as compound E1, Step 2 (59% yield), Step 3 (27% yield), Step 4 (59% yield), Step 5 (quantitative yield), Procedure 6 (28% yield), in which 2-bromodibenzofuran [86-76-0] is used as compound E3. MS (HPLC-MS): m / z (retention time) = 912.1 (8.51 minutes). Example 2 has an emission maximum (2 wt % in PMMA) of 471 nm, a full width at half maximum (FWHM) of 0.13 eV (24 nm), CIEx and CIEy coordinates of 0.12 and 0.19, respectively, and a PLQY of 59%.

[0159] Additional Examples of Organic Molecules of the Invention [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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Claims

1. a first chemical moiety comprising the structure of any one of the following formulae Ia, Ib, and Ic: 【Chemistry 1】 ...Chemical formula I-a 【Chemistry 2】 ...Chemical formula I-b 【Transformation 3】 ...Chemical formula I-c an organic molecule comprising a second chemical moiety comprising the structure of any one of the following chemical formulae II-a-1, II-a-2, II-a-3, II-a-4, II-a-5, II-a-6 and II-a-7: 【Chemistry 4】 ...Chemical formula II-a-1 【Transformation 5】 ...Chemical formula II-a-2 【Transformation 6】 ...Chemical formula II-a-3 【Transformation 7】 ...Chemical formula II-a-4 【Transformation 8】 ...Chemical formula II-a-5 【Chemistry 9】 ...Chemical formula II-a-6 【Chemistry 10】 ...Chemical formula II-a-7 wherein the first chemical moiety is attached to the second chemical moiety via a single bond; # is the attachment site between the first and second chemical moieties; R X , R XII , R XV and R ＸＶＩＩＩ are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , SiMe 3 , SiPh 3 , Ph optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph)2; R 9 , at each occurrence, is independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , and Ph optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF 3 and Ph; In the second chemical portion, the dotted line represents a single bond connecting the second chemical moiety to the first chemical moiety; X 1 is selected from the group consisting of C(R 17 ) 2 , NR 15 , O and S; R 15 , R 16 , and R 17 , at each occurrence, are independently selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 , and Ph optionally substituted with one or more substituents independently selected from the group consisting of deuterium, Me, i Pr, t Bu, CN, CF 3 and Ph.

2. The organic molecule of claim 1 , wherein the first chemical moiety comprises a structure according to Formula Ia.

3. The first chemical moiety comprises a structure according to formula Ia, where R ９ is in each case hydrogen or deuterium.

4. The organic molecule of any one of claims 1 to 3, wherein the second chemical moiety comprises a structure according to any one of formulas II-a-1 and II-a-6:

5. Use of an organic molecule according to any one of claims 1 to 4 as a light emitter in an optoelectronic device.

6. The use of claim 5, wherein the optoelectronic device is selected from the group consisting of: Organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and down conversion devices.

7. A composition comprising: (a) an organic molecule according to any one of claims 1 to 4, in particular in emitter and / or host form; (b) an emitter material and / or a host material different from the organic molecule; and (c) optionally, a dye and / or a solvent.

8. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 4 or a composition according to claim 7.

9. 9. The optoelectronic device of claim 8, having 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, an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a down conversion device.

10. -substrate, -anode, a cathode, and - comprises a light-emitting layer, the anode or the cathode is disposed on the substrate; 10. The optoelectronic device according to claim 8 or claim 9, wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or the composition.

11. 10. A method for producing an optoelectronic device, in which an organic molecule according to any one of claims 1 to 4 or a composition according to claim 7 is used, in particular comprising a step of processing said organic molecule by a vacuum evaporation method or from a solution.

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