Organic molecules for optoelectronic devices

Abstract

The present invention relates to an organic molecule for use in an optoelectronic device. According to the invention, said organic molecule comprises: a first chemical moiety having the structure of formula I, and [Case 1] JPEG2023547440000097.jpg6269 ...Chemical formula I - one or two second chemical moieties having the structure of formula II, [Case 2] JPEG2023547440000098.jpg6256 ...Chemical formula II Here, R Z is a single bond attachment site linking a first chemical moiety to a second chemical moiety; R Y is a single bond attachment site connecting a first chemical moiety to a second chemical moiety, or R a and The dotted lines "----" indicate the site of attachment of the first chemical moiety to the second chemical moiety.

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] This objective is achieved by the present invention, which provides novel organic molecules. Organic electroluminescent devices, including one or more organic light-emitting layers, 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 electroluminescent devices that essentially use inorganic materials, organic electroluminescent devices are typically flexible and can be produced, particularly 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.

[0004] Therefore, there is an unmet need in the art for optoelectronic devices that have high quantum yield, long lifetime, and excellent color purity.

[0005] 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]

[0006] The organic molecules according to the present invention exhibit an emission maximum in the deep blue, sky blue, or green spectral range, preferably in the deep blue and sky blue spectral range, and most preferably in the deep blue spectral range. The organic molecules exhibit an emission maximum in particular between 420 nm and 520 nm, preferably between 440 nm and 495 nm, and more preferably between 450 nm and 470 nm. The excited state lifetime is 5 μs or less.

[0007] Furthermore, the molecules of the present invention exhibit particularly narrow emission spectra with small full widths at half maximum (FWHM). The emission spectra of the organic molecules preferably exhibit a full width at half maximum (FWHM) of 0.15 eV or less (≦0.15 eV), measured at 1% by weight of the emitter in poly(methyl methacrylate) (PMMA) at room temperature (i.e., about 25° C.), unless otherwise specified. The excited state lifetime of the organic molecules according to the present invention is particularly 5 μs or less.

[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 in the device. Consequently, the corresponding OLEDs have higher stability than OLEDs with known emitter materials and comparable hues, and / or, when the molecules according to the invention are used in OLED displays, they more accurately reproduce natural-looking hues, i.e., achieve higher resolution in the displayed images. 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, resulting in light emission. [Brief explanation of the drawings]

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

[0010] The organic molecule according to the present invention comprises or consists of: a first chemical moiety comprising the structure of Formula I, and [ka] ...Chemical formula I - exactly one or two second chemical moieties comprising the structure of formula II, [ka] ...Chemical formula II where R Z is, in each case, a single bond attachment site connecting a first chemical moiety to a second chemical moiety; R Y In each case, the first chemical moiety is converted into a second chemical moiety R a or R a and In Formula II, the dotted line "----" indicates the site of attachment of the first chemical moiety to the second chemical moiety (R Z Both and / or R Y In one embodiment of the organic molecule having only one second chemical moiety, this is Z is bonded to the R Y is R a is.

[0011] R a is independently selected in each occurrence from the group consisting of: hydrogen, deuterium, N(R 5 )2, OR 5 , SR 5 , CF3, CN, Halogens (F, Cl, Br, I), C1-C 40 Alkyl, This is a group consisting of one or more substituents R 5 optionally replaced by where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 optionally replaced by C1-C 40 Alkoxy, This is a group consisting of one or more substituents R 5 optionally replaced by where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 optionally replaced by C1-C 40 thioalkoxy, This is a group consisting of one or more substituents R 5 optionally replaced by where one or more non-adjacent CH groups are R 5 C=CR 5 , C≡C, Si(R 5 )2, Ge(R 5 )2, Sn(R 5 )2, C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO2, NR 5 , O, S or CONR 5 optionally replaced by C6-C 60 aryl, This is a group consisting of one or more substituents R 5 optionally substituted with C3-C 57 heteroaryl, This is a group consisting of one or more substituents R 5 optionally replaced by R 5 is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, halogens, C1-C 12 Alkyl, wherein optionally one or more hydrogen atoms are independently selected from R 6 is replaced by C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently selected from R 6 is replaced by, and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently selected from R 6 is replaced by R 6 is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, halogens, C1-C 12 Alkyl, C6-C 18 aryl, wherein optionally one or more hydrogen atoms are independently replaced with a C1-C5 alkyl substituent; and C3-C 15 heteroaryl, wherein optionally one or more hydrogen atoms are independently replaced with a C1-C5 alkyl substituent; 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 , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is independently selected in each occurrence from the group consisting of: hydrogen, deuterium, N(R 4 )2, OR 4 , SR 4 , Si(R 4 )3. B(OR 4 )2, OSO2R4 , CF3, CN, halogen, C1-C 40 Alkyl, This is a group consisting of one or more substituents R 4 optionally replaced by where one or more non-adjacent CH groups are R 4 C=CR 4 , C≡C, Si(R 4 )2, Ge(R 4 )2, Sn(R 4 )2, C=O, C=S, C=Se, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 optionally replaced by C1-C 40 Alkoxy, This is a group consisting of one or more substituents R 4 optionally replaced by where one or more non-adjacent CH groups are R 4 C=CR 4 , C≡C, Si(R 4 )2, Ge(R 4 )2, Sn(R 4 )2, C=O, C=S, C=Se, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 optionally replaced by C1-C 40 thioalkoxy, This is a group consisting of one or more substituents R 4 optionally replaced by where one or more non-adjacent CH groups are R 4 C=CR 4 , C≡C, Si(R 4 )2, Ge(R 4 )2, Sn(R 4 )2, C=O, C=S, C=Se, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4, O, S or CONR 4 optionally replaced by C2-C 40 alkenyl, This is a group consisting of one or more substituents R 4 optionally replaced by where one or more non-adjacent CH groups are R 4 C=CR 4 , C≡C, Si(R 4 )2, Ge(R 4 )2, Sn(R 4 )2, C=O, C=S, C=Se, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 optionally replaced by C2-C 40 Alkynyl, This is a group consisting of one or more substituents R 4 optionally replaced by where one or more non-adjacent CH groups are R 4 C=CR 4 , C≡C, Si(R 4 )2, Ge(R 4 )2, Sn(R 4 )2, C=O, C=S, C=Se, C=NR 4 , P(=O)(R 4 ), SO, SO2, NR 4 , O, S or CONR 4 optionally replaced by C6-C 60 aryl, This is a group consisting of one or more substituents R 4 optionally substituted with C3-C 57 heteroaryl, This is a group consisting of one or more substituents R 4 optionally replaced by R 4 are, in each occurrence independently selected from the group consisting of: Hydrogen, deuterium, halogen, OPh (Ph = phenyl), SPh, CF3, CN, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN, or CF; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN, or CF; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN, or CF; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN, or CF; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN, or CF; C6-C 18 aryl, This is a group consisting of one or more substituents R 5 optionally replaced by C3-C 17 heteroaryl, This is a group consisting of one or more substituents R 5 optionally replaced by N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl), where the substituents R a are optionally joined together to form an aryl ring, which is optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3.

[0012] In one embodiment of the present invention, an organic molecule according to the present invention comprises or consists of: a first chemical moiety comprising the structure of Formula I, and - two second chemical moieties, comprising the structure of Formula II. 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 , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, tN(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0013] 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 XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0014] 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 XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF3, F, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0015] 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 XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, iPr, t Bu, F, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0016] 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 XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0017] 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 XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII, R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0018] In a preferred embodiment of the present invention, R XIII and R XII is hydrogen. In a preferred embodiment of the present invention, R XV and R XIX is hydrogen. In a preferred embodiment of the present invention, R I and R X is hydrogen. In certain embodiments of the present invention, R I , R V , R XV and R XIX is hydrogen. In certain embodiments of the present invention, R I , R V , R VI and R X is hydrogen. In certain embodiments of the present invention, R I , R V , R VI , R X , R XV and R XIX is hydrogen.

[0019] In one embodiment of the present invention, R XI is independently selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF3, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0020] In a preferred embodiment of the present invention, R XI is independently selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0021] In a more preferred embodiment of the present invention, R XI is independently selected from the group consisting of: Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0022] In one embodiment of the present invention, R XI is independently selected from the group consisting of: Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0023] In certain embodiments of the present invention, R XI Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0024] In one embodiment of the present invention, R XI is N(Ph)2.

[0025] In one embodiment of the present invention, R Y is a single bond attachment site that connects a first chemical moiety to a second chemical moiety.

[0026] In one embodiment of the present invention, R a is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t aryl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, iPr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph. In a further embodiment of the present invention, R a is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t Carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0027] In a further embodiment of the present invention, R a is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, F Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0028] In a further embodiment of the present invention, R a is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0029] In a further embodiment of the present invention, R a is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0030] In a further embodiment of the present invention, R ais, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0031] In one embodiment of the present invention, R a is, independently in each occurrence, selected from the group consisting of: hydrogen, and Ph.

[0032] In one embodiment of the present invention, R a is hydrogen in each case. In a preferred embodiment of the present invention, R V =R X and R I =R VI is. In one embodiment of the present invention, R 5 is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph. In one embodiment of the present invention, R 5 is, independently in each occurrence, selected from the group consisting of: hydrogen, and Ph.

[0033] In one embodiment of the present invention, R 5 is hydrogen in each case.

[0034] In one embodiment of the present invention, the organic molecule comprises or consists of a structure of formula II-a and II-b: [ka] ...Chemical formula II-a [ka] ...Chemical formula II-b , is.

[0035] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where 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 , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0036] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0037] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF3, F, and Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0038] In one embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0039] In one embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , RXVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0040] In one embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0041] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R I and R X is hydrogen.

[0042] In certain embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R I , R V , R VI and R X is hydrogen.

[0043] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R XIII and R XII is hydrogen.

[0044] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R XV and R XIX is hydrogen.

[0045] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R I and R X is hydrogen.

[0046] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R I , R V , R XV and R XIX is hydrogen.

[0047] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R I , R V , R VI and R X is hydrogen.

[0048] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R I , R V , R VI , R X , R XV and R XIX is hydrogen.

[0049] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R XI is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0050] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R XI is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me, i Pr,t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0051] In another preferred embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0052] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0053] In certain embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas II-a, II-b, where R XI is, in each case independently, Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0054] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R XI is, independently in each occurrence, N(Ph)2.

[0055] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas II-a and II-b, where R a is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t aryl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me,i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0056] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formula II-a, II-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t Carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0057] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formula II-a, II-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, tcarbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0058] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formula II-a, II-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0059] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formula II-a, II-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, tN(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0060] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formula II-a, II-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0061] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formula II-a, II-b, where R V =R X and R I =R VI is.

[0062] In a preferred embodiment of the invention, the organic molecule comprises or consists of the structure of formula II-a: [ka] ...Chemical formula II-a . In a more preferred embodiment of the invention, the organic molecule comprises or consists of a structure of formula II-a, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0063] In one embodiment of the invention, the organic molecule comprises or consists of a structure of formula II-a, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0064] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of formula II-a, where R XI is, in each case independently, Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0065] In one embodiment of the invention, the organic molecule comprises or consists of a structure of formula II-a, where R XI is, independently in each occurrence, N(Ph)2.

[0066] In other embodiments of the present invention, the organic molecule comprises or consists of a structure of formula III-a and III-b: [ka] ...Chemical formula III-a [ka] ...Chemical formula III-b .

[0067] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where 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 , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, ttriazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0068] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, tcarbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0069] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph. In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R II , R III , R IV , R V , R VI , R VII, R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph.

[0070] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, F, Me, i Pr,t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0071] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII is, independently in each occurrence, selected from the group consisting of: hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0072] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I and R X is hydrogen.

[0073] In certain embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R V , R VI and RX is hydrogen.

[0074] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XIII and R XII is hydrogen.

[0075] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XV and R XIX is hydrogen.

[0076] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I and R X is hydrogen.

[0077] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R V , R XV and R XIX is hydrogen.

[0078] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R V , R VI and R X is hydrogen. In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R I , R V , R VI , R X , R XV and R XIXis hydrogen. In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XI is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0079] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XI is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0080] In a more preferred embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr,t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0081] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0082] In certain embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XI is, in each case independently, Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0083] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R XI is, independently in each occurrence, N(Ph)2.

[0084] In one embodiment of the present invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF3, F, Me, i Pr, t aryl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0085] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F and Ph; Me, i Pr, t Carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, F, and Ph; and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0086] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, F, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph; Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0087] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me,i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0088] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, wherein R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0089] In further embodiments of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R a is, independently in each occurrence, selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0090] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure according to any of formulas III-a and III-b, where R V =R X and R I =R VI is.

[0091] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula III-b: [ka] ...Chemical formula III-b , is.

[0092] In a preferred embodiment of the invention, the second chemical moiety is comprised of a structure of formula II-0a, II-0b, or II-0c: [ka] ...Chemical formula II-0a [ka] ...Chemical formula II-0b [ka] ...Chemical formula II-0c , is.

[0093] In a more preferred embodiment of the present invention, the organic molecule comprises or consists of a structure of formula II-0a, II-0b, and II-0c, wherein R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Bu, Me,i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu, F, and Ph.

[0094] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-0a, II-0b, and II-0c, where R XI is, independently in each occurrence, selected from the group consisting of: Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph, and Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0095] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-0a, II-0b, and II-0c, where R XI is, in each case independently, Me, i Pr, t N(Ph)2 optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0096] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-0a, II-0b, and II-0c, where R XI is N(Ph)2.

[0097] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-0a, II-0b, and II-0c, where R XIII is hydrogen in each case.

[0098] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-0a, II-0b, and II-0c, where R XII is hydrogen in each case.

[0099] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of formula II-0a, II-0b, and II-0c, where R XIII and R XII is hydrogen in each case.

[0100] In a preferred embodiment of the invention, the second chemical moiety is comprised of the structure of formula II-I: [ka] ...Chemical formula II-I , is.

[0101] In a preferred embodiment of the invention, the second chemical moiety is comprised of the structure of Formula II-II: [ka] ...Chemical formula II-II , is.

[0102] As used throughout this specification, the term "cyclic group" is understood in the broadest sense to refer to any monocyclic, bicyclic or polycyclic moiety.

[0103] 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.

[0104] 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.

[0105] 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 are in each case identical or different and 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 can, of course, be substituted with hydrogen or any other substituent defined in a specific embodiment of the present invention.

[0106] As used throughout this specification, the term "aromatic ring system" is also understood in its broadest sense as any bicyclic or polycyclic aromatic moiety.

[0107] As used throughout this specification, the term "heteroaromatic ring system" is also understood in its broadest sense as any bicyclic or polycyclic heteroaromatic moiety.

[0108] 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.

[0109] 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 numbers 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.

[0110] 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, 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 groups that can be attached through any position of an aromatic or heteroaromatic group derived from 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.

[0111] 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.

[0112] 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), ... ethyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (E 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- des-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexades-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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] As used throughout this specification, the term "thioalkoxy" includes linear, branched and cyclic thioalkoxy substituents, where the O in the exemplary alkoxy group is replaced with an S.

[0117] 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.

[0118] 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 whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above ways of describing a substituent or attached fragment are considered equivalent.

[0119] 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. Therefore, there are many well-known methods by which this can be achieved and many review articles describing them (e.g., A. Michelotti, M. Roche, Synthesis 2019, 51(06), 1319-1328, DOI:10.1055 / s-0037-1610405; J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. Int. Ed. 2007, 46(15), 7744-7765, DOI:10.1002 / anie.200700039; Y. Sawama, Y. Monguchi, H. Sajiki, Synlett 2012, 23(7), 959-972, DOI:10.1055 / s-0031-1289696).

[0120] The excited state lifetime is composed of many components. For example, in the case of TADF emitters, it consists of prompt fluorescence, which is usually on the order of nanoseconds, and delayed fluorescence, which is usually on the order of microseconds. The prompt fluorescence is insignificant because the delayed fluorescence is three times larger, which means that the excited state lifetime can also be estimated as the lifetime of the delayed fluorescence.

[0121] In one embodiment, the organic molecules according to the present invention have an excited state lifetime of 10 μs or less, 8 μs or less, in particular 6 μs or less, more preferably 5 μs or less or 4 μs or less, and even more preferably 3 μs or less or 2 μs or less, in a PMMA (poly(methyl methacrylate)) film containing 1-5 wt %, in particular 1 wt %, of the organic molecules at room temperature (i.e., about 25° C.).

[0122] 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 has a value less than

[0123] In a further embodiment of the present invention, the organic molecules according to the present invention have an excited state lifetime of 10 μs or less, 8 μs or less, in particular 6 μs or less, more preferably 5 μs or less or 4 μs or less, even more preferably 3 μs or less or 2 μs or less, with a full width at half maximum value of less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.15 eV or even less than 0.12 eV, in a PMMA (poly(methyl methacrylate)) film containing 1 to 5 wt. %, in particular 1 wt. % of the organic molecules, at room temperature (i.e. about 25° C.).

[0124] In one embodiment, the organic molecules according to the invention have an excited state lifetime of 10 μs or less, 7 μs or less, in particular 5 μs or less, more preferably 2 μs or less or 1 μs or less in a PMMA (poly(methyl methacrylate)) film containing 1 wt % of the organic molecules at room temperature.

[0125] Unless otherwise stated, in the context of the organic molecules according to the invention, the excited state lifetime is equivalent to and / or determined by the delayed fluorescence lifetime or delayed fluorescence decay time.

[0126] 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 380 nm to 800 nm, and have a full width at half maximum (FWHM) value of less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.15 eV, or even less than 0.12 eV in a PMMA (poly(methyl methacrylate)) film containing 1 wt. % of the organic molecules at room temperature.

[0127] 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 with 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.

[0128] 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 of the maximum intensity of the absorption spectrum. 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 the emitter) at 77 K.

[0129] 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% by weight of emitter).

[0130] 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 at half maximum of the maximum intensity of the emission spectrum.

[0131] 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.

[0132] 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.

[0133] An optoelectronic device is understood in the broadest sense as any device based on 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 nm to 800 nm.

[0134] 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.

[0135] The light-emitting electrochemical cell comprises three layers: a cathode, an anode, and an active layer comprising organic molecules according to the present invention.

[0136] 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.

[0137] In one embodiment, the light-emitting layer of an organic light-emitting diode comprises organic molecules according to the present invention.

[0138] 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.

[0139] 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.

[0140] In a further embodiment of the invention, the composition has a photoluminescence quantum yield (PLQY) at room temperature of greater than 5%, preferably greater than 10%, more preferably greater than 20%, even more preferably greater than 40%, even more preferably greater than 60% or even greater than 70%.

[0141] Compositions with at least one additional emitter One embodiment of the present invention relates to a composition comprising or consisting of: (i) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (ii) 5 to 98% by weight, preferably 30 to 93.9% by weight, in particular 40 to 88% by weight, of one host compound H, (iii) 1 to 30% by weight, in particular 1 to 20% by weight, preferably 1 to 5% by weight, of at least one additional emitter molecule F having a structure different from that of the molecules according to the invention, (iv) optionally 0 to 94% by weight, preferably 0.1 to 65% by weight, in particular 1 to 50% by weight, of at least one additional host compound D having a structure different from that of the molecules according to the invention, and (v) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent. The ingredients and the composition are selected so that the sum of the weights of the ingredients is 100%.

[0142] In a further embodiment of the present invention, the composition has an emission peak in the visible or near ultraviolet range, i.e. in the wavelength range of 380 nm to 800 nm.

[0143] In one embodiment of the present invention, the at least one additional emitter molecule F is a purely organic emitter.

[0144] In one embodiment of the present invention, the at least one additional emitter molecule F is a purely organic TADF emitter. Purely organic TADF emitters are widely known from the state of the art, e.g., Wong and Zysman-Colman ("Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light-Emitting Diodes.", Adv. Mater. 2017, 29(22), 1605444-1605498, DOI: 10.1002 / adma.201605444).

[0145] In one embodiment of the present invention, the at least one additional emitter molecule F is a fluorescent emitter, in particular a blue, green, yellow or red fluorescent emitter.

[0146] In a further embodiment of the invention, the composition comprising at least one additional emitter molecule F has an emission peak in the visible or near-ultraviolet range, i.e. in the wavelength range from 380 nm to 800 nm, with a half-width value at room temperature of less than 0.30 eV, in particular less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.19 eV or even less than 0.17 eV, the lower half-width limit being 0.05 eV.

[0147] Compositions in which at least one additional emitter molecule F is a green fluorescent emitter In a further embodiment of the invention, the at least one additional emitter molecule F is a fluorescent emitter, in particular a green fluorescent emitter.

[0148] In one embodiment, the at least one additional emitter molecule F is a fluorescent emitter selected from the group consisting of: [ka] [ka]

[0149] In a further embodiment of the invention, the composition has an emission peak in the visible or near-ultraviolet range, i.e. in the wavelength range of 380 nm to 800 nm, in particular 485 nm to 590 nm, preferably 505 nm to 565 nm, more preferably 515 nm to 545 nm.

[0150] Compositions in which at least one additional emitter molecule F is a red fluorescent emitter In a further embodiment of the invention, the at least one additional emitter molecule F is a fluorescent emitter, in particular a red fluorescent emitter.

[0151] In one embodiment, the at least one additional emitter molecule F is a fluorescent emitter selected from the group consisting of: [ka] [ka] [ka] [ka] [ka]

[0152] In a further embodiment of the invention, the composition has an emission peak in the visible or near-ultraviolet range, i.e. in the wavelength range of 380 nm to 800 nm, in particular 590 nm to 690 nm, preferably 610 nm to 665 nm, more preferably 620 nm to 640 nm.

[0153] Emission layer EML In one embodiment, the light-emitting layer EML of the organic light-emitting diode of the present invention comprises (or consists essentially of) a composition comprising or consisting of: (i) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 30 to 94.9% by weight, in particular 40 to 89% by weight, of at least one host compound H, (iii) optionally 0 to 94% by weight, preferably 0.1 to 65% by weight, in particular 1 to 50% by weight, of at least one additional host compound 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 at least one additional emitter molecule F having a structure different from that of the molecules according to the invention.

[0154] Preferably, energy is 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 E 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 E according to the invention.

[0155] 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).

[0156] 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).

[0157] an emissive layer EML comprising at least one additional host compound D; In a further embodiment, the emissive layer EML of the organic light-emitting diode of the present invention comprises (or consists essentially of) a composition comprising or consisting of: (i) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 30 to 94.9% by weight, in particular 40 to 89% by weight, of at least one host compound H, (iii) 0 to 94% by weight, preferably 0.1 to 65% by weight, in particular 1 to 50% by weight, of at least one additional host compound 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 at least one additional emitter molecule F having a structure different from that of the molecules according to the invention.

[0158] In one embodiment of the organic light-emitting diode of the present 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.

[0159] 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.

[0160] In one embodiment of the organic light-emitting diode of the present 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 HOMOThe 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 LUMO The 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.

[0161] an emitting layer EML comprising at least one additional emitter molecule F; In a further embodiment, the emissive layer EML of the organic light-emitting diode of the present invention comprises (or consists essentially of) a composition comprising or consisting of: (i) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (ii) 5 to 98% by weight, preferably 30 to 93.9% by weight, in particular 40 to 88% by weight, of at least one host compound H, (iii) 1 to 30% by weight, in particular 1 to 20% by weight, preferably 1 to 5% by weight, of at least one additional emitter molecule F having a structure different from that of the molecules according to the invention, (iv) optionally 0 to 94% by weight, preferably 0.1 to 65% by weight, in particular 1 to 50% by weight, of at least one additional host compound D having a structure different from that of the molecules according to the invention, and (v) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent.

[0162] In a further embodiment, the emissive layer EML comprises (or consists essentially of) a composition denoted composition with at least one additional emitter, including at least one additional emitter molecule F defined in composition, wherein the at least one additional emitter molecule F is a green fluorescent emitter.

[0163] In a further embodiment, the emissive layer EML comprises (or consists essentially of) a composition denoted composition with at least one additional emitter, including at least one additional emitter molecule F defined in composition, wherein the at least one additional emitter molecule F is a red fluorescent emitter.

[0164] In one embodiment of the emissive layer EML comprising at least one additional emitter molecule F, energy is transferred from one or more organic molecules E according to the present invention to the at least one additional emitter molecule F, in particular from the first excited singlet state S1(E) of the one or more organic molecules E according to the present invention to the first excited singlet state S1(F) of the at least one additional emitter molecule F.

[0165] In one embodiment, the first excited singlet state S1(H) of one host compound H of the emissive layer is higher in energy than the first excited singlet state S1(E) of one or more organic molecules E of the present invention (S1(H)>S1(E)), and the first excited singlet state S1(H) of one host compound H is higher in energy than the first excited singlet state S1(F) of at least one emitter molecule F (S1(H)>S1(F)).

[0166] In one embodiment, the first excited triplet state T1(H) of one host compound H is higher in energy than the first excited triplet state T1(E) of one or more organic molecules E of the present invention (T1(H)>T1(E)), and the first excited triplet state T1(H) of one host compound H is higher in energy than the first excited triplet state T1(F) of at least one emitter molecule F (T1(H)>T1(F)).

[0167] In one embodiment, the first excited singlet state S1(E) of one or more organic molecules E of the present invention is higher in energy than the first excited singlet state S1(F) of at least one emitter molecule F (S1(E)>S1(F)).

[0168] In one embodiment, the first excited triplet state T1(E) of one or more organic molecules E of the present invention is higher in energy than the first excited triplet state T1(F) of at least one emitter molecule F (T1(E)>T1(F)).

[0169] In one embodiment, the first excited triplet state T1(E) of one or more organic molecules E of the present invention is higher in energy than the first excited triplet state T1(F) of at least one emitter molecule F (T1(E)>T1(F)), wherein the absolute value of the energy difference between T1(E) and T1(F) is greater than 0.3 eV, preferably greater than 0.4 eV, or even greater than 0.5 eV.

[0170] In one embodiment, the host compound H has an energy E in the range of −5 to −6.5 eV. 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).

[0171] 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).

[0172] In one embodiment, 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 LUMO The 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.

[0173] 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 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.

[0174] In one embodiment, host compound D is a TADF material and host compound H is a TADF material having a luminescence wavelength of 2500 cm -1 Larger ΔE ST In certain embodiments, host compound D is a TADF material and 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.

[0175] In one embodiment, host compound H is a TADF material and 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).

[0176] 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.

[0177] 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.

[0178] In one embodiment of the optoelectronic device of the present invention, the organic molecule E according to the present invention is used as the emissive material of the emissive layer EML.

[0179] 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.

[0180] 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 optionally comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may also comprise one or more layers of each layer type defined above.

[0181] Additionally, 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.

[0182] 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, the OLED optionally comprises each layer selected from the group of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may also comprise one or more layers of each layer type defined above.

[0183] 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.

[0184] 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.

[0185] The substrate can be made of any material or composition of materials. Most commonly, 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.

[0186] 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).

[0187] 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 serve 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-carbazol-1-yl)phenylamine. The HTL may also include a star-shaped heterocycle such as (tris-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.

[0188] 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).

[0189] The light-emitting layer (EML) is generally 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 one or more light-emitting molecules E 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.

[0190] Alternatively, the EML further comprises one or more host materials H, where the host is a triplet-triplet annihilation (TTA) material. The TTA material can convert energy from a first excited triplet state T1 to a first excited singlet state S1 by triplet-triplet annihilation. The TTA material should be selected such that the lowest excited triplet state energy level T1 of the TTA material is twice greater than the lowest excited singlet state energy level of the emissive molecule of the present invention, i.e., 2T1 (TTA material) > S1 (emissive molecule of the present invention).

[0191] 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 emissive 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.

[0192] An electron transport layer (ETL) can be disposed adjacent to the light-emitting layer (EML). Any electron transporter can be used here. For example, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone can be used. The electron transporter can 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.

[0193] 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).

[0194] A cathode layer C can be disposed adjacent to the electron transport layer (ETL). The cathode layer C can, 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 can also consist of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively, or in addition, the cathode layer C can also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C can also consist of nanoscale silver wires.

[0195] 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.

[0196] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds H.

[0197] The emitting layer EML may further include one or more additional emitter molecules F to further modify the emission spectrum 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 have 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 spectrum 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 light that is red-shifted 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).

[0198] Optionally, the optoelectronic device (e.g., OLED) may also be, for example, an essentially white optoelectronic device. For example, such a white optoelectronic device may also comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Optionally, there may then be energy transfer between the two or more molecules, as described above.

[0199] 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

[0200] 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.

[0201] Deep blue emitters can preferably have a maximum emission of less than 480 nm, more preferably less than 470 nm, even more preferably less than 465 nm, or even less than 460 nm. The maximum emission is typically greater than 420 nm, preferably greater than 430 nm, more preferably greater than 440 nm, or even greater than 450 nm.

[0202] Thus, a further aspect of the present invention is a 3 and / or have an external quantum efficiency of greater than 8%, preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15% or even greater than 20% at 420 nm to 500 nm, preferably 430 nm to 490 nm, more preferably 440 nm to 480 nm, even more preferably 450 nm to 470 nm, and / or have an emission maximum of 500 cd / m 3 and OLEDs exhibiting an LT80 value of greater than 100 h, preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, or even greater than 1000 h. Accordingly, a further aspect of the present invention relates to OLEDs whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20, even more preferably less than 0.15, or even less than 0.10.

[0203] A further aspect of the present invention relates to OLEDs that emit light at a well-defined color point. According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the present invention emits light with an FWHM of the main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.18 eV, even more preferably less than 0.15 eV, or even less than 0.12 eV.

[0204] A further aspect of the present invention relates to OLEDs that emit light at well-defined color points. According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In one aspect, the OLED according to the present invention emits light with an excited state lifetime of 10 μs or less, 8 μs or less, particularly 6 μs or less, more preferably 5 μs or less or 4 μs or less, even more preferably 3 μs or less or 2 μs, and with an FWHM of the main emission peak of less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.18 eV, even more preferably less than 0.15 eV, or even less than 0.12 eV.

[0205] 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.

[0206] In a further aspect, the present invention relates to a method for fabricating optoelectronic components, in which the organic molecules of the present invention are used.

[0207] 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 processed or printed.

[0208] 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 can be deposited using the same or different deposition methods.

[0209] 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]

[0210] General synthesis method I [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0211] General procedure for synthetic AAV1: [ka] E1a (1.00 equivalents), E1b (1.50 equivalents), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.02 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalents) and sodium tert-butoxide (NaO t Bu, 3.00 equiv.) in toluene under a nitrogen atmosphere is stirred at 110 °C for 48 h. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I1 as a solid.

[0212] General procedure for synthetic AAV2: [ka] I1 (1.00 equiv.), 3-chloroiodobenzene (1.20 equiv., CAS: 625-99-0), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.02 equiv., CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalents) and sodium tert-butoxide (NaO t Bu, 2.00 equiv.) in toluene under a nitrogen atmosphere is stirred at 110 °C for 260 h. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I2 as a solid.

[0213] General procedure for synthetic AAV3: [ka] I2 (1.00 equiv.), E3 (2.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.02 equiv., CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu)3, CAS: 13716-12-6, 0.08 equivalents) and sodium tert-butoxide (NaO t Bu, 2.00 equiv.) in toluene under a nitrogen atmosphere is stirred at 110 °C for 260 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I3 as a solid.

[0214] General procedure for synthetic AAV2a: [ka] E1a-a (1.00 equiv.), 1-bromo-3-chloro-5-fluorobenzene (1.20 equiv., CAS: 33863-76-2), and tripotassium phosphate (2.5 equiv., CAS: 7778-53-2) are stirred in dimethyl sulfoxide (DMSO) under a nitrogen atmosphere for 16 hours at 120 °C. After cooling to room temperature (rt), the reaction mixture is added to water. The precipitate is filtered. The resulting crude product is purified by recrystallization or column chromatography to give I2a as a solid.

[0215] General procedure for synthetic AAV3a: [ka] E3a (1.00 equiv.), I2a (1.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO tBu, 5.00 equiv.) in toluene under a nitrogen atmosphere is stirred at 80 °C for 26 h. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I3a as a solid.

[0216] General procedure for synthetic AAV4: [ka] I3 (1.00 equiv.), I3a (1.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO t Bu, 2.00 equiv.) in toluene under a nitrogen atmosphere is stirred at 105 °C for 12 h. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I4 as a solid.

[0217] General procedure for synthetic AAV5: [ka] Under a nitrogen atmosphere, boron tribromide (CAS 10294-33-4, 6.00 equiv.) is slowly added to a solution of I4 (1.00 equiv.) in o-dichlorobenzene. The reaction mixture is stirred at 180 °C overnight, cooled to room temperature, and quenched by the addition of N,N-diisopropylethylamine (CAS 7087-68-5, 16.0 equiv.). The reaction mixture is extracted with dichloromethane and water, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give P1 as a solid.

[0218] General synthesis method II RI=RX,…RV=RVI [ka] [ka] [ka]

[0219] General procedure for synthetic AAV6: [ka] E4 (1.00 equiv.), 1,3-dibromo-5-fluorobenzene (1.20 equiv., CAS: 135-67-1), and tripotassium phosphate (2.5 equiv., CAS: 7778-53-2) are stirred in dimethyl sulfoxide (DMSO) under a nitrogen atmosphere at 120 °C for 144 h. After cooling to room temperature (rt), the reaction mixture is added to water. The precipitate is filtered. The resulting crude product is purified by recrystallization or column chromatography to give I5 as a solid.

[0220] General procedure for synthetic AAV7: [ka] I3 (2.00 equiv.), I5 (1.00 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu)3, CAS: 13716-12-6, 0.04 equivalents) and sodium tert-butoxide (NaO t Bu, 5.00 equiv.) in toluene under a nitrogen atmosphere is stirred at 100 °C for 3 h. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give I6 as a solid.

[0221] General procedure for synthetic AAV8: [ka] Under a nitrogen atmosphere, boron tribromide (CAS 10294-33-4, 8.00 equiv.) is slowly added to a solution of I6 (1.00 equiv.) in o-dichlorobenzene. The reaction mixture is stirred at 190 °C for 24 h, cooled to room temperature, and quenched by the addition of N,N-diisopropylethylamine (CAS 7087-68-5, 16.0 equiv.). The reaction mixture is extracted with dichloromethane and water, and the phases are separated. The combined organic layers are dried over MgSO4, and the solvent is removed under reduced pressure. The resulting crude product is purified by recrystallization or column chromatography to give P2 as a solid.

[0222] 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).

[0223] 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.

[0224] 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.

[0225] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC) Steady-state emission spectroscopy was recorded using a Model FluoroMax-4 (Horiba Scientific) equipped with a 150 W xenon-Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and time-correlated single-photon counting options. Standard correction fits were used to correct the emission and excitation spectra.

[0226] Excited state lifetimes are determined using the same system using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub. Excitation light source: NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns) NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm)

[0227] Data analysis (exponential fit) is performed using the software suite DataStation and DAS6 analysis software. The fit is determined using the chi-squared test.

[0228] 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. The FS5 is configured with a xenon lamp providing a broad spectrum. The continuous light source is a 150W xenon arc lamp, and a specific wavelength is selected using a Czerny-Turner monochromator, which is also used to set the specific emission wavelength. 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. The specific lifetime, τ, is i and the corresponding amplitude A iThe delayed fluorescence lifetime τ is calculated by weighting it by DF is determined.

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[0229] Photoluminescence quantum yield measurements Photoluminescence quantum yield (PLQY) measurements were performed using an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics). Quantum yields and CIE coordinates were determined using software U6039-05 version 3.6.0. The emission maxima are given in nm, the quantum yields Φ are given in % and the CIE coordinates are given as x,y values. PLQY is determined using the following protocol: 1) Quality assurance: Anthracene (known concentration) in ethanol is used as a reference. 2) Excitation wavelength: The maximum absorption of an organic molecule is determined and this 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:

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[0230] 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%.

[0231] OLEDs (not fully optimized) are characterized by measuring their electroluminescence spectra using standard methods and their intensity- and current-dependent external quantum efficiency (%), calculated using the light and current detected by a photodiode. The lifetime of an OLED device is extracted from the change in luminance when operated at a constant current density. The LT50 value corresponds to the time at which the measured luminance has decreased to 50% of the initial luminance; similarly, LT80 corresponds to the time at which the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the time at which the measured luminance has decreased to 95% of the initial luminance. Accelerated lifetime measurements are performed (e.g., applying increased current densities, e.g., 500 cd / m 3 In the present invention, the LT80 value is determined using the following formula:

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[0232] HPLC-MS HPLC-MS analysis is performed on an Agilent HPLC (1260 series) equipped with an MS detector (Thermo LTQ XL). For example, a typical HPLC method is as follows: A reversed-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 room temperature (rt) with the following gradient: [Table 1] The following mixed solvents containing 0.1% formic acid were also used: [Table 2] From a solution of analyte at a concentration of 0.5 mg / mL, an injection volume of 2 μL is taken for the measurement.

[0233] 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.

[0234] Example 1 [ka] Example 1 is synthesized by: AAV1 (77% yield), in which 5-chloro-N1,N1,N3,N3-tetraphenyl-1,3-benzenediamine [1630850-28-0] was used as compound E1a and aniline [62-53-3] was used as compound E1b, MS (HPLC-MS): m / z (retention time) = 504.4 (4.04 min), AAV2 (80% yield), MS (HPLC-MS): m / z (retention time) = 614 (5.1 minutes), AAV3 (46% yield), where aniline [62-53-3] was used as compound E3, MS (HPLC-MS): m / z (retention time) = 671.6 (4.68 min), AAV2a (54% yield), where phenoxazine [135-67-1] was used as E1a-a, MS (GC-MS): m / z (retention time) = 373 (8.6 min); AAV3a (49% yield), where diphenylamine [122-39-4] was used as compound E3a, MS (GC-MS): m / z (retention time) = 460 (11.95 min), AAV4 (50% yield), MS (HPLC-MS): m / z (retention time) = 1096 (7.20 minutes), AAV5 (8% yield), MS (HPLC-MS): m / z (retention time) = 1120 (8.47 minutes).

[0235] Example 1 (1 wt % in PMMA) has an emission maximum of 475 nm with a full width at half maximum (FWHM) of 0.15 eV (28 nm), CIE x and CIE y coordinates of 0.12 and 0.23, respectively, and an excited state lifetime of 4.7 μs.

[0236] Example 2 [ka] Example 2 is synthesized by: AAV1 (77% yield), in which 5-chloro-N1,N1,N3,N3-tetraphenyl-1,3-benzenediamine [1630850-28-0] was used as compound E1a and aniline [62-53-3] was used as compound E1b, MS (HPLC-MS): m / z (retention time) = 504.4 (4.05 min), AAV2 (80% yield), MS (HPLC-MS): m / z (retention time) = 615 (5.12 minutes), AAV3 (46% yield), where aniline [62-53-3] was used as compound E3, MS (HPLC-MS): m / z (retention time) = 671.9 (4.76 min), AAV6 (25% yield), where phenoxazine [135-67-1] was used as E4, MS (GC-MS): m / z (retention time) = 417 (9.04 min), AAV7 (80% yield), MS (HPLC-MS): m / z (retention time) = 1598.5 (8.27 minutes), AAV8 (1% yield), MS (HPLC-MS): m / z (retention time) = 1629 (9.32 minutes).

[0237] Example 2 (1 wt % in PMMA) has an emission maximum of 480 nm with a full width at half maximum (FWHM) of 0.13 eV (24 nm), CIEx and CIEy coordinates of 0.16 and 0.36, respectively, and an excited state lifetime of 1.25 μs.

[0238] Comparative Example C1 [ka] Comparative Example C1 (1 wt % in PMMA) has an emission maximum of 452 nm with a full width at half maximum (FWHM) of 0.23 eV (40 nm), CIEx and CIEy coordinates of 0.15 and 0.11, respectively, and an excited state lifetime of 0.45 ms.

[0239] Additional Examples of Organic Molecules of the Invention [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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Claims

1. An organic molecule having a structure of chemical formula III-a or III-b: 【Chemistry 1】 ...Chemical formula III-a 【Chemistry 2】 ...Chemical formula III-b where: R a is independently selected at each occurrence from the group consisting of: Hydrogen, Me, i Pr, t Bu, and Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, and Ph; R XI is, independently in each occurrence: N(Ph) 2 optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, and Ph; R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ , R Ｘ ,R XII,R ＸＩＩＩ , R ＸＩＶ , R ＸＶ , R ＸＶＩ , R ＸＶＩＩ , R ＸＶＩＩＩ , R ＸＩＸ , R ＸＸ , R ＸＸＩ , R ＸＸＩＩ and R ＸＸＩＩＩ is independently selected in each occurrence from the group consisting of: hydrogen, Me, i Pr, t Bu, CN, CF 3 , F, and Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , F, and Ph.

2. Chemical Formula II in Chemical Formula III-a and III-b: 【Transformation 3】 The organic molecule of claim 1, wherein the second chemical moiety is comprised of a structure of Formula II-0a, Formula II-0b, or Formula II-0c: 【Chemistry 4】 ...Chemical formula II-0a 【Transformation 5】 ...Chemical formula II-0b 【Transformation 6】 ...Chemical formula II-0c wherein R XI , R XII , R XIII , R XIV , R XV , R XVI , R XVII , R XVIII , R XIX , R XX , R XXI , R XXII and R XXIII are defined as in claim 1 .

3. 3. Use of an organic molecule according to claim 1 or 2 as a light emitter in an optoelectronic device.

4. 4. The use according to claim 3, 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.

5. A composition comprising: (a) the organic molecule according to claim 1 or 2; (b) an emitter material and / or a host material different from the organic molecule; and (c) optionally, a dye and / or a solvent.

6. An optoelectronic device comprising an organic molecule according to claim 1 or 2, or a composition according to claim 5.

7. 7. The optoelectronic device of claim 6, 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.

8. -substrate, -anode, a cathode, and - comprises a light-emitting layer, the anode or the cathode is disposed on the substrate; 8. The optoelectronic device according to claim 6, wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or the composition.

9. A method for producing an optoelectronic device, in which the organic molecule according to claim 1 or 2 or the composition according to claim 5 is used.

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