Organic molecules for optoelectronic devices

Abstract

The present invention relates to an organic molecule for an optoelectronic device. According to the invention, said organic molecule comprises: a first chemical moiety having the structure of Formula I; and [Formula 1] JPEG2023540458000075.jpg3741 ...Chemical formula I two second chemical moieties having the structure of formula II; [chemical 2] JPEG2023540458000076.jpg6441 ...Chemical formula II Where: X and Y, in each occurrence, are selected independently from the group consisting of B and N; Z is a direct bond; R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X R represents, independently in each occurrence, the attachment position of a single bond connecting said first chemical moiety to said second chemical moiety, and * is selected from the group consisting of R * are in each case independently of one another: hydrogen, deuterium, OPh, SPh, CF 3 , CN, F, Si(C 1 -C 5 Alkyl) 3 , Si(Ph) 3 , C 1 -C 5 Alkyl, C 1 -C 5 Alkoxy, C 1 -C 5 Thioalkoxy, C 2 -C 5 Alkenyl, C 2 -C 5 Alkynyl, C 6 -C 18 Aryl, C3 -C 17 Heteroaryl, N(C 6 -C 18 Aryl) 2 , N(C 3 -C 17 Heteroaryl) 2 , and N(C 3 -C 17 Heteroaryl)(C 6 -C 18 aryl), The dotted line indicates the point of attachment of the first chemical moiety to the second chemical moiety.

Description

[Technical Field]

[0001] The present invention relates to organic 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] These objectives are achieved by the present invention, which provides novel organic molecules.

[0004] According to the present invention, the organic molecules are purely organic, i.e., they do not contain any metal ions, in contrast to the metal complexes known to be used in optoelectronic devices. However, the organic molecules of the present invention contain metalloids, in particular B, Si, Sn, Se and / or Ge. [Effects of the Invention]

[0005] According to the present invention, the organic molecules exhibit an emission maximum in the blue, sky blue, green, or yellow 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, or the organic molecules exhibit an emission maximum, in particular, between 490 nm and 600 nm, preferably between 510 nm and 560 nm, and more preferably between 520 nm and 540 nm. The photoluminescence quantum yield of the organic molecules according to the present invention is, in particular, 50% or more. The use of the molecules according to the present invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), leads to increased device efficiency or color purity, which is expressed as the full width at half maximum (FWHM) of the device's emission. The corresponding OLEDs have even higher stability than OLEDs with known emitter materials and similar hues. DETAILED DESCRIPTION OF THE INVENTION

[0006] The organic molecule according to the present invention comprises or consists of: a first chemical moiety comprising or consisting of the structure of Formula I; and [ka] ...Chemical formula I two second chemical moieties comprising or consisting of the structure of formula II; [ka] ...Chemical formula II where: X and Y, in each occurrence, are selected independently from the group consisting of B and N; R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X are, in each occurrence independently of one another, the attachment position of the single bond connecting the first chemical moiety to the second chemical moiety and R * is selected from the group consisting of R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh (Ph = phenyl), SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0007] In Formula II, the dotted line "----" indicates the point of attachment of the first chemical moiety to the second chemical moiety; Z is a direct bond; o is, independently in each occurrence, an integer of 0 or 1; p is, independently in each occurrence, an integer of 0 or 1; R 2 are selected, independently in each occurrence, from the group consisting of: hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(OR 5 )2, OSO2R5 , CF3, CN, F, 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 C2-C 40 alkenyl, 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 C2-C 40 Alkynyl, 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 is optionally replaced by

[0008] R 5 are selected, independently in each occurrence, from the group consisting of: hydrogen, deuterium, N(R 6 )2, OR 6 , Si(R 6 )3. B(OR 6 )2, OSO2R 6 , CF3, CN, F, Br, I, C1-C 40 Alkyl, This is a group consisting of one or more substituents R 6 optionally replaced by where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 optionally replaced by C1-C 40 Alkoxy, This is a group consisting of one or more substituents R 6 optionally replaced by where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 optionally replaced by C1-C 40 thioalkoxy, This is a group consisting of one or more substituents R 6 optionally replaced by where one or more non-adjacent CH groups are R6 C=CR 6 , C≡C, SI(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 optionally replaced by C2-C 40 alkenyl, This is a group consisting of one or more substituents R 6 optionally replaced by where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 optionally replaced by C2-C 40 Alkynyl, This is a group consisting of one or more substituents R 6 optionally replaced by where one or more non-adjacent CH groups are R 6 C=CR 6 , C≡C, Si(R 6 )2, Ge(R 6 )2, Sn(R 6 )2, C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO2, NR 6 , O, S or CONR 6 optionally replaced by C6-C 60 aryl, This is a group consisting of one or more substituents R 6 optionally substituted with C3-C 57 heteroaryl, This is a group consisting of one or more substituents R6 is optionally replaced by

[0009] R 6 are selected, independently in each occurrence, from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl), where: Adjacent substituent R 2are optionally joined together to form an aryl or heteroaryl ring, which is optionally substituted with one or more C1-C5 alkyl substituents, deuterium, halogen, CN, or CF3; exactly two selected from the group consisting of X and Y are B, and exactly two selected from the group consisting of X and Y are N; R I and R II , R II and R III ,and R IV and R V two adjacent substituents selected from the group consisting of: indicate the attachment points of the single bonds linking the first chemical moiety to the second chemical moiety to form a ring; R VI and R VII , R VII and R VIII ,and R IX and R X Two adjacent substituents selected from the group consisting of indicate the attachment points of a single bond that connects a first chemical moiety to another second chemical moiety (e.g., second) to form a ring.

[0010] The organic molecule does not have more than two second chemical moieties.

[0011] Specific examples of organic molecules are shown below: [ka] [ka] In a preferred embodiment, X is B and Y is N. In other embodiments, one X is B and one X is N.

[0012] In a preferred embodiment, o is 0 or 1 and p is 0 or 1.

[0013] In a preferred embodiment, o is 1.

[0014] In a preferred embodiment, p is 0 and o is 1.

[0015] In a more preferred embodiment, X is B, Y is N, p is 0, and o is 1.

[0016] In one embodiment, both o and p are 0.

[0017] In one embodiment of the present invention, R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0018] In a further embodiment of the present invention, R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0019] In one embodiment, R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0020] In one embodiment, R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0021] In one embodiment, R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0022] In a preferred embodiment, R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0023] In certain embodiments, R 2 is hydrogen in each case.

[0024] In one embodiment, R* is, at each occurrence independently of each other, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0025] In a preferred embodiment, R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0026] In certain embodiments, R * is hydrogen in each case.

[0027] In one embodiment, the organic molecule comprises or consists of the structure of Formulas Ia and Ib: [ka] ...Chemical formula Ia [ka] ...Chemical formula Ib where m is 0 or 1, n is 0 or 1, Exactly two selected from the group consisting of X and Y are B, and exactly two selected from the group consisting of X and Y are N.

[0028] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia and Ib, where o is 1.

[0029] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia and Ib, where o is 1 and p is 0.

[0030] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia and Ib, where o is 1, p is 0, exactly one selected from m and n is 1, and exactly one selected from n and m is 0.

[0031] In one embodiment, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0032] In one embodiment of the invention, the organic molecule comprises or consists of the structure of formula Ia and Ib, where R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0033] In further embodiments of the invention, the organic molecule comprises or consists of a structure of formula Ia and Ib, wherein R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0034] In one embodiment, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0035] In one embodiment, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0036] In a preferred embodiment, R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0037] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R 2 is hydrogen in each case.

[0038] In one embodiment, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0039] In preferred embodiments, the organic molecule comprises or consists of the structure of formula Ia and Ib, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0040] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R * is hydrogen in each case.

[0041] In one embodiment, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0042] In preferred embodiments, the organic molecule comprises or consists of the structure of formula Ia and Ib, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0043] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ia and Ib, where R 2 and R * is hydrogen in each case.

[0044] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia and Ib, wherein o, p, n, and m are 0.

[0045] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia: [ka] ...Chemical formula Ia wherein exactly two selected from the group consisting of X and Y are B, and exactly two selected from the group consisting of X and Y are N.

[0046] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where o is 1:

[0047] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where o is 1, p is 0, exactly one selected from m and n is 1, and exactly one selected from n and m is 0.

[0048] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0049] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr,t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0050] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula Ia, wherein R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0051] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0052] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0053] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0054] In certain embodiments, the organic molecule comprises or consists of a structure of Formula Ia, where R 2 is hydrogen in each case.

[0055] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0056] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0057] In certain embodiments, the organic molecule comprises or consists of a structure of Formula Ia, where R *is hydrogen in each case.

[0058] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0059] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0060] In certain embodiments, the organic molecule comprises or consists of a structure of Formula Ia, where R 2 and R * is hydrogen in each case.

[0061] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia, where o, p, n, and m are 0.

[0062] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib: [ka] ...Chemical formula Ib wherein exactly two selected from the group consisting of X and Y are B, and exactly two selected from the group consisting of X and Y are N.

[0063] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where o is 1:

[0064] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where o is 1, p is 0, exactly one selected from m and n is 1, and exactly one selected from n and m is 0.

[0065] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0066] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr,t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0067] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula Ib, wherein R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0068] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0069] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0070] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0071] In certain embodiments, the organic molecule comprises or consists of a structure of Formula Ib, where R 2 is hydrogen in each case.

[0072] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0073] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0074] In certain embodiments, the organic molecule comprises or consists of a structure of Formula Ib, where R *is hydrogen in each case.

[0075] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0076] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0077] In certain embodiments, the organic molecule comprises or consists of a structure of Formula Ib, where R 2 and R * is hydrogen in each case.

[0078] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib, where o, p, n, and m are 0.

[0079] In one embodiment, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb: [ka] ...Chemical formula IIa [ka] ...Chemical formula IIb

[0080] In one embodiment, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0081] In one embodiment, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0082] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R 2 are, in each occurrence independently of one another, selected from the group consisting of: hydrogen, Me, i Pr, tBu, CN, CF3, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0083] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, tpyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0084] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0085] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0086] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R 2 is hydrogen in each case.

[0087] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0088] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0089] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula I, wherein exactly two second chemical moieties comprise a structure selected from the group consisting of Formulas IIa and IIb, wherein R * is hydrogen in each case.

[0090] In one embodiment, the organic molecule comprises or consists of the structure of Formula I, wherein exactly two second chemical moieties consist of the structure of Formula IIa: [ka] . ...Chemical formula IIa

[0091] In one embodiment, the organic molecule comprises or consists of the structure of Formula I, wherein exactly two second chemical moieties consist of the structure of Formula IIb: [ka] . ...Chemical formula IIb

[0092] In one embodiment, the organic molecule comprises or consists of a structure of one of Formulas Ia-I, Ia-II, Ia-III, and Ia-IV: [ka] ...Chemical formula Ia-I [ka] ...Chemical formula Ia-II [ka] ...Chemical formula Ia-III [ka] ...Chemical formula Ia-IV

[0093] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0094] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0095] In a further embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0096] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0097] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, I Pr, t Bu, SIMe3, SIPh3, and Me, I Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph. In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, I Pr, and Ph optionally substituted with one or more Ph substituents.

[0098] In certain embodiments, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R 2 is hydrogen in each case.

[0099] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0100] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0101] In certain embodiments, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R * is hydrogen in each case.

[0102] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0103] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0104] In certain embodiments, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ia-I, Ia-II, Ia-III, and Ia-IV, wherein R 2 and R * is hydrogen in each case.

[0105] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV: [ka] ...Chemical formula Ib-I [ka] ...Chemical formula Ib-II [ka] ...Chemical formula Ib-III [ka] ...Chemical formula Ib-IV

[0106] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0107] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formula Ib-I, Ib-II, Ib-III, and Ib-IV, wherein R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0108] In a further embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, wherein R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0109] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0110] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0111] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0112] In certain embodiments, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 is hydrogen in each case.

[0113] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0114] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0115] In certain embodiments, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R * is hydrogen in each case.

[0116] In one embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0117] In a preferred embodiment, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0118] In certain embodiments, the organic molecule comprises or consists of a structure selected from the group consisting of formulas Ib-I, Ib-II, Ib-III, and Ib-IV, where R 2 and R * is hydrogen in each case.

[0119] In one embodiment, the organic molecule comprises or consists of the structure of Formula Iaa: [ka] ...Chemical formula Iaa where R Z is the attachment position of the single bond connecting the first chemical moiety to the second chemical moiety of Formula IIa.

[0120] In one embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0121] In one embodiment of the invention, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0122] In a further embodiment of the invention, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr,t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0123] In one embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, SI(C1-C5 alkyl)3, SI(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0124] In one embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0125] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0126] In certain embodiments, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 is hydrogen in each case.

[0127] In one embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, tBu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0128] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0129] In certain embodiments, the organic molecule comprises or consists of the structure of formula Iaa, where R * is hydrogen in each case.

[0130] In one embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0131] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0132] In certain embodiments, the organic molecule comprises or consists of the structure of formula Iaa, where R 2 and R * is hydrogen in each case.

[0133] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia-I: [ka] ...Chemical formula Ia-I

[0134] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia-II: [ka] ...Chemical formula Ia-II

[0135] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba: [ka] ...Chemical formula Iba where R Y is the attachment position of the single bond connecting the first chemical moiety to the second chemical moiety of Formula IIb.

[0136] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0137] In one embodiment of the invention, the organic molecule comprises or consists of a structure of formula Iba, where R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0138] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula Iba, where R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0139] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0140] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0141] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iba, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0142] In certain embodiments, the organic molecule comprises or consists of a structure of formula Iba, where R 2 is hydrogen in each case.

[0143] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, tBu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0144] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iba, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0145] In certain embodiments, the organic molecule comprises or consists of a structure of formula Iba, where R * is hydrogen in each case.

[0146] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0147] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iba, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0148] In certain embodiments, the organic molecule comprises or consists of a structure of formula Iba, where R 2 and R * is hydrogen in each case.

[0149] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia-III: [ka] ...Chemical formula Ia-III

[0150] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ia-IV: [ka] ...Chemical formula Ia-IV

[0151] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba: [ka] ...Chemical formula Iba where R Z is the attachment position of the single bond connecting the first chemical moiety to the second chemical moiety of Formula IIa.

[0152] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0153] In one embodiment of the invention, the organic molecule comprises or consists of a structure of formula Iba, where R 2 is independently 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0154] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula Iba, where R 2 is independently 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, and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0155] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0156] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0157] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iba, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0158] In certain embodiments, the organic molecule comprises or consists of a structure of formula Iba, where R 2 is hydrogen in each case.

[0159] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, tBu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0160] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iba, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0161] In certain embodiments, the organic molecule comprises or consists of a structure of formula Iba, where R * is hydrogen in each case.

[0162] In one embodiment, the organic molecule comprises or consists of a structure of formula Iba, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0163] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Iba, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0164] In certain embodiments, the organic molecule comprises or consists of a structure of formula Iba, where R 2 and R * is hydrogen in each case.

[0165] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib-I: [ka] ...Chemical formula Ib-I

[0166] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib-II: [ka] ...Chemical formula Ib-II

[0167] In one embodiment, the organic molecule comprises or consists of a structure of formula Ibb: [ka] ...Chemical formula Ibb where R Y is the attachment position of the single bond connecting the first chemical moiety to the second chemical moiety of Formula IIb.

[0168] In one embodiment, the organic molecule comprises or consists of a structure of formula Ibb, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0169] In one embodiment of the invention, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, t pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; N(Ph)2.

[0170] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 are, in each occurrence independently of one another, 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, and Ph; Me, i Pr, tpyridinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t pyrimidinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0171] In one embodiment, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF3, CN, F, Si(C1-C5 alkyl)3, Si(Ph)3, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium (D), CN, CF or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF or F; C6-C 18 aryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; C3-C 17 heteroaryl, which is optionally substituted with one or more C1-C5 alkyl substituents, Ph, CN, CF3 or F; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl).

[0172] In one embodiment, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0173] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ibb, where R 2 are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0174] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 is hydrogen in each case.

[0175] In one embodiment, the organic molecule comprises or consists of a structure of formula Ibb, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, tBu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0176] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ibb, where R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0177] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ibb, where R * is hydrogen in each case.

[0178] In one embodiment, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, Me, i Pr, t Bu, SiMe3, SiPh3, and Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

[0179] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ibb, where R 2 and R * are, in each occurrence independently of one another, selected from the group consisting of: Hydrogen, deuterium, i Pr, and Ph optionally substituted with one or more Ph substituents.

[0180] In certain embodiments, the organic molecule comprises or consists of a structure of formula Ibb, where R 2 and R * is hydrogen in each case.

[0181] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib-III: [ka] ...Chemical formula Ib-III

[0182] In one embodiment, the organic molecule comprises or consists of the structure of Formula Ib-IV: [ka] ...Chemical formula Ib-IV

[0183] 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. Furthermore, throughout this specification, the number of aromatic ring atoms may be given in subscript numerals in the definitions of specific 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 having two binding sites to other molecular structures and serving as a linker structure. If a group in an exemplary embodiment 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.

[0184] In particular, as used throughout this specification, the term "aryl group" or "heteroaryl group" includes 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 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 group that can be attached through any position of an aromatic or heteroaromatic group derived from a combination of the aforementioned groups.

[0185] As used throughout this specification, the term "cyclic group" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0186] As used throughout this specification, the term "biphenyl" as a substituent is also understood in its broadest sense as ortho-biphenyl, meta-biphenyl or para-biphenyl, where ortho, meta and para are defined with respect to the point of attachment to another chemical moiety.

[0187] As used throughout this specification, the term "terphenyl" as a substituent is also understood in its broadest sense as 3-ortho-terphenyl, 4-ortho-terphenyl, 4-meta-terphenyl, 5-meta-terphenyl, 2-para-terphenyl or 3-para-terphenyl, where ortho, meta and para are defined in relation to the points of attachment of the phenyl moiety to each other, and "2-", "3-", "4-" and "5-" are defined in relation to the points of attachment to other chemical moieties, i.e. as follows: [ka] 3-ortho-terphenyl [ka] 4-ortho-terphenyl [ka] 4-meta-terphenyl [ka] 5-meta-terphenyl [ka] 2-meta-terphenyl [ka] 2-para-terphenyl where # indicates the point of attachment to another chemical moiety.

[0188] As used throughout this specification, the term "naphthyl" is also understood in its broadest sense as a naphthalene substituent, 1-naphthyl and 2-naphthyl, where "1-" and "2-" refer to the points of attachment to other chemical moieties, i.e., as defined below: [ka] 1-Naphthyl [ka] 2-Naphthyl where # indicates the point of attachment to another chemical moiety.

[0189] As used throughout this specification, the term "anthracene" is also understood in its broadest sense as a substituent to be 1-anthracenyl, 2-anthracenyl and 9-anthracenyl, where "1-", "2-" and "9-" refer to the points of attachment to other chemical moieties, i.e., as defined below: [ka] 1-anthracenyl [ka] 2-anthracenyl [ka] 9-anthracenyl where # indicates the point of attachment to another chemical moiety.

[0190] The term "alkyl group" as used throughout this specification is understood in the broadest sense as any linear, branched or cyclic alkyl substituent. In particular, the term "alkyl" includes the substituents methyl (Me), ethyl (Et), n-propyl (N-propyl), ... ethyl (Et), n-propyl (N-propyl), methyl (Me), ethyl (Et), ethyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl (Et), propyl n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-butyl ( i Bu), s-butyl ( s Bu), t-butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n -octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n- 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadece-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec- 1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadece-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

[0191] 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.

[0192] 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.

[0193] 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.

[0194] The term "thioalkoxy" as used throughout this specification includes linear, branched and cyclic thioalkoxy substituents, where O in the exemplary alkoxy group is replaced with S.

[0195] The terms "halogen" and "halo" as used throughout this specification are also understood in the broadest sense, preferably fluorine, chlorine, bromine or iodine.

[0196] Wherever hydrogen (H) is mentioned herein, it is also substituted with deuterium in each instance.

[0197] 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.

[0198] In one embodiment of the present invention, in DCM containing 0.001 mg / mL of the organic molecule at room temperature, the organic molecule according to the present invention has an emission peak in the visible or near-ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, with a full width at half maximum of less than 0.35 eV, preferably less than 0.30 eV, more preferably less than 0.26 eV, even more preferably less than 0.22 eV, and even more preferably less than 0.18 eV.

[0199] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperatures, typically 77 K. Phosphorescence is typically visible in the steady-state spectrum of a film of 2% emitter and 98% poly(methyl methacrylate) (PMMA). Therefore, the triplet energy is also determined as the onset of the phosphorescence spectrum. For fluorescent emitter molecules, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K.

[0200] The onset of the emission spectrum is determined by calculating the intersection of the tangent to the emission spectrum with the x-axis, which is set at the high energy side of the emission band and the half maximum intensity of the emission spectrum.

[0201] In one embodiment, the organic molecule according to the present invention has an emission spectrum onset that is energetically close to the emission maximum in DCM containing 0.001 mg / mL of the organic molecule at room temperature, i.e. the energy difference between the emission spectrum onset and the energy of the emission maximum is less than 0.14 eV, preferably less than 0.13 eV, more preferably less than 0.12 eV, and the full width at half maximum (FWHM) of the organic molecule is less than 0.35 eV, preferably less than 0.30 eV, more preferably less than 0.26 eV, even more preferably less than 0.22 eV, more preferably less than 0.18 eV, resulting in a CIE y coordinate of less than 0.20, preferably less than 0.18, more preferably less than 0.16, more preferably less than 0.14.

[0202] 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.

[0203] A preferred embodiment relates to the use of organic molecules according to the invention as light emitters in optoelectronic devices.

[0204] 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.

[0205] In the context of 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

[0206] In a preferred embodiment in the context of such an application, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC) and a light emitting transistor.

[0207] For said applications, in the light-emitting layer of an optoelectronic device, in particular an OLED, the fraction of the organic molecules according to the invention is 0.1% to 99% by weight, in particular 1% to 80% by weight. In an alternative embodiment, the proportion of said organic molecules in the light-emitting layer is 100% by weight.

[0208] In one embodiment, the emissive layer comprises 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.

[0209] A further aspect of the present invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention in emitter form; (b) one or more triplet-triplet annihilation (TTA) host substances different from the organic molecules of the present invention; (c) optionally, one or more TADF materials, and (d) optionally, one or more dyes and / or one or more solvents.

[0210] A further aspect of the present invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention in emitter form; (b) one or more host materials different from the organic molecules according to the present invention, and (c) one or more TADF materials.

[0211] A further aspect of the present invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention in emitter form; (b) one or more host materials different from the organic molecules according to the present invention, and (c) one or more phosphorescent materials.

[0212] In certain embodiments, the emissive layer EML comprises (or consists essentially of) a composition comprising or consisting of: (i) 0.1 to 10% by weight, preferably 0.5 to 5% by weight, in particular 1 to 3% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight, of one or more host compounds H, (iii) 0.9 to 94.9% by weight, preferably 14.5 to 80% by weight, in particular 24 to 77% by weight, of one or more additional host compounds D having a structure different from that of the molecules according to the invention, (iv) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent, and (V) optionally 0 to 30% by weight, in particular 0 to 20% by weight, preferably 0 to 5% by weight, of one or more additional emitter molecules F having a structure different from that of the molecules according to the invention.

[0213] Compositions Having One or More TTA Host Materials In a preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer B comprises (or consists of): (i) 10 to 84 wt% of TTA substance H N , (ii) 0 to 30 wt% of TADF material E B , (iii) 0.1 to 10% by weight of an emitter according to the invention, and optionally (iv) 0 to 74 wt. % of one or more solvents.

[0214] In a preferred embodiment, the sum of the percentages of (I) to (iv) is 100% by weight.

[0215] In another preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer B comprises (or consists of): (i) 56 to 90 wt% of TTA substance H N , (ii) 0 to 5 wt% of TADF material E B , (iii) 0.5 to 5% by weight of an emitter according to the invention, and optionally (iv) 0 to 34 wt. % of one or more solvents.

[0216] In a preferred embodiment, the sum of the percentages (i) to (iv) is 100% by weight.

[0217] Compositions with one or more TADF materials In one embodiment, the light-emitting layer B comprises: (i) 10 to 89.9 wt. % of one or more p-host compounds H P , (ii) 0 to 79.9 wt. % of one or more n-host compounds H N , (iii) 10 to 50 wt % of one or more TADF materials E B , (iv) 0.1 to 10% by weight of one or more emitters according to the present invention, and (v) 0 to 79.9 wt. % of one or more solvents.

[0218] In one embodiment, the light-emitting layer B comprises: (i) 22 to 87.5 wt. % of one or more p-host compounds H P , (ii) 0 to 65.5 wt. % of one or more n-host compounds H N , (iii) 12 to 40 wt. % of one or more TADF materials E B , (iv) 0.5 to 5% by weight of one or more emitters according to the present invention, and (V) 0 to 65.5 wt. % of one or more solvents.

[0219] Compositions with one or more phosphorescent materials H N In an optional preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer B comprises (or consists of): (i) 10 to 84.9 wt % of the host compound H P , (ii) 0 to 84.9 wt % of the host compound H N , (iii) 5 to 15% by weight of phosphorescent material E B , (iv) 0.1 to 10% by weight of an emitter according to the invention, and optionally (v) 0 to 84.9 wt. % of one or more solvents.

[0220] H N In an optional preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer B comprises (or consists of): (i) 22 to 70.5 wt % of the host compound H P , (ii) 0 to 72.5 wt % of the host compound H N , (iii) 5 to 10% by weight of phosphorescent material E B , (iv) 0.5 to 5% by weight of an emitter according to the invention, and optionally (v) 0 to 72.5 wt. % of one or more solvents.

[0221] 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.

[0222] 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).

[0223] 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).

[0224] 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, and still more preferably −0.1 eV to 0.1 eV, E LUMO (H)>ELUMO (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, and still more preferably -0.1 eV to 0.1 eV.

[0225] 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 corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) of less than ST The TADF material preferably has a 3000 cm -1 less than, more preferably, 1500 cm -1 less than, even more preferably, 1000 cm -1 less than 500 cm -1 Less than ΔE ST Indicates the value.

[0226] 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 More than 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.

[0227] 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 More than ΔE ST In certain embodiments, host compound H is a TADF material and 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).

[0228] In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition of the type 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.

[0229] 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.

[0230] In one embodiment of the optoelectronic device of the present invention, the organic molecule E according to the present invention is used as emissive material in the emissive layer EML.

[0231] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the composition according to the present invention as described herein.

[0232] 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 includes layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0233] Additionally, the optoelectronic device, in one embodiment, also includes at least one protective layer that protects the device from damaging exposure to harmful substances in the environment, including, for example, moisture, vapors and / or gases.

[0234] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0235] 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 includes layers selected from the group consisting of HIL, HTL, EBL, HBL, ETL, and EIL, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0236] 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 typical 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.

[0237] 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.

[0238] The substrate can be made of any material or composition of materials. Most often, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver, or aluminum film) or a plastic film or slide can be used, which allows for a higher level of flexibility. The anode layer A is made of a material that allows for a nearly (essentially) transparent film. To allow light emission from the OLED, at least one of the two electrodes must be (essentially) transparent, so either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists 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.

[0239] 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).

[0240] The hole transport layer (HTL) is generally located adjacent to the anode layer A or the hole injection layer (HIL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles can also be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the light-emitting layer (EML). The hole transport layer (HTL) can also function as an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) may be formed of tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′,4″-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or 9,9′-diphenyl-6-(9-phenyl-9H- The HTL may also include a star-shaped heterocycle such as (carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer composed of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopant may be, for example, a transition metal oxide such as vanadium oxide, molybdenum oxide, or tungsten oxide. The organic dopant may be, for example, tetrafluorotetracyanoquinodimethane (F4-TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz), or a transition metal complex.

[0241] 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).

[0242] 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.

[0243] In one embodiment of the present invention, the EML comprises a so-called mixed host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one light-emitting organic molecule according to the present invention, T2T as the electron-dominant host, and one selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole as the hole-dominant host. In a further embodiment, the EML comprises 50 to 80% by weight, preferably 60 to 75% by weight, of a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 10 to 45% by weight, preferably 15 to 30% by weight, of T2T, and 5 to 40% by weight, preferably 10 to 30% by weight, of an emissive molecule according to the present invention.

[0244] An electron transport layer (ETL) may be located adjacent to the light-emitting layer (EML). Any electron transporter may be used here. For example, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may also include 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum tris(8-hydroxyquinoline) (Alq), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO), 2,7-di(2,2′-bipyridin-5-yl)triphenyl (BPyTP), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), and / or 4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-biphenyl (BTB). Optionally, the ETL is also doped with a material such as Liq. The electron transporting layer (ETL) can also block holes, or a hole blocking layer (HBL) is introduced.

[0245] 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).

[0246] Adjacent to the electron transport layer (ETL) can be a cathode layer C. The cathode layer C can comprise or consist of, for example, 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 additionally, 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.

[0247] 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.

[0248] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds H.

[0249] The emitting layer EML may further include one or more additional emitter molecules F to further modify the emission and / or absorption spectrum of the emitting layer EML. Such emitter molecules F may be any emitter molecule known in the art. Preferably, such emitter molecules F are molecules having a structure different from that of molecules E according to the present invention. The emitter molecules F may also be TADF emitters. Alternatively, the emitter molecules F may also be fluorescent and / or phosphorescent emitter molecules capable of shifting the emission and / or absorption spectrum of the emitting layer EML. For example, triplet and / or singlet excitons may be transferred from the organic emitter molecules according to the present invention to the emitter molecules F before relaxing to the ground state S, typically emitting red-shifted light compared to the light emitted by the organic molecules. Optionally, the emitter molecules F may also induce a two-photon effect (i.e., absorption of two photons at half the maximum absorption energy).

[0250] Optionally, the optoelectronic device (e.g., OLED) can also be, for example, an essentially white optoelectronic device. For example, such a white optoelectronic device can include at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Optionally, there can then be energy transfer between the two or more molecules, as described above.

[0251] As used herein, unless more specifically defined in a particular context, the designations for the hue 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 For emitter molecules, such hue refers to the emission maximum. 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.

[0252] The green emitter may preferably have an emission maximum of 500 to 560 nm, more preferably 510 to 550 nm, and even more preferably 520 to 540 nm.

[0253] Yet another embodiment of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, such as UHD-TVs. In this context, the term "close" refers to the range of CIEx and CIEy coordinates provided at the end of the paragraph. While commercial applications typically use top light-emitting elements (where the top electrode is transparent), the test elements used throughout this invention refer to bottom light-emitting elements (where the bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits a CIEX color coordinate of 0.06 to 0.34, preferably 0.07 to 0.29, more preferably 0.09 to 0.24, even more preferably 0.12 to 0.22, and even more preferably 0.14 to 0.19, and / or a CIEy color coordinate of 0.44 to 0.84, preferably 0.55 to 0.83, more preferably 0.65 to 0.82, and even more preferably 0.70 to 0.81, and even more preferably 0.75 to 0.8.

[0254] Therefore, a further aspect of the present invention is a method for manufacturing a 14500 cd / m 2 The present invention relates to an OLED that exhibits an external quantum efficiency of 10% or more, preferably 13% or more, more preferably 15% or more, even more preferably 17% or more, and even more preferably 20% or more, and / or an OLED that exhibits maximum emission in the range of 495 nm to 580 nm, preferably 500 nm to 560 nm, more preferably 510 nm to 550 nm, and even more preferably 515 nm to 540 nm.

[0255] The deep blue emitter may preferably have a maximum emission of less than 480 nm, more preferably less than 470 nm, even more preferably less than 465 nm, and even more preferably less than 460 nm. The maximum emission will typically be 420 nm or greater, preferably 430 nm or greater, more preferably 440 nm or greater, and even more preferably 450 nm or greater.

[0256] Thus, a further aspect of the present invention is a 2 an OLED that exhibits an external quantum efficiency of 8% or more, preferably 10% or more, more preferably 13% or more, even more preferably 15% or more, and even more preferably 20% or more at 420 nm to 500 nm, preferably 430 nm to 490 nm, more preferably 440 nm to 480 nm, and even more preferably 450 nm to 470 nm; and / or an OLED that exhibits a maximum emission wavelength of 500 cd / m 2 and an LT80 value of 100 h or more, preferably 200 h or more, more preferably 400 h or more, even more preferably 750 h or more, and even more preferably 1000 h or more. Accordingly, a further aspect of the present invention relates to an OLED having an emission exhibiting 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, and even more preferably less than 0.10.

[0257] Yet another 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 having a narrow emission bandwidth (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 0.20 eV, even more preferably less than 0.19 eV, and even more preferably less than 0.17 eV.

[0258] Yet another 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. Therefore, a further aspect of the present invention relates to an OLED whose emission exhibits a CIEX color coordinate 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, and even more preferably 0.10 to 0.15, and / or a CIEy color coordinate 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, and even more preferably 0.04 to 0.10.

[0259] In a further aspect, the present invention relates to a method for producing an optoelectronic component, in which the organic molecules of the present invention are used.

[0260] The optoelectronic device, in particular the OLED according to the present invention, may be produced by any means of vapor deposition and / or liquid processes. Thus, at least one layer may be - Produced by the sublimation process; - Manufactured by organic vapor phase deposition process, - Produced by a carrier gas sublimation process, - Solution processed or printed.

[0261] The methods used to manufacture 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.

[0262] 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.

[0263] [Example] General Synthesis Method I General synthetic scheme I provides a synthetic scheme for organic molecules according to the invention, where R III =R VIII and R II , R IV , R VII and R IX is hydrogen, Adjacent substituent R V and R VI indicates the attachment position of a single bond linking a first chemical moiety to a second chemical moiety to form a ring; Two adjacent substituents R X and R I indicates the attachment position of a single bond linking a first chemical moiety to another (e.g., second) second chemical moiety to form a ring where X is B, Y is N, and o and p are 0: [ka] I0 (1.00 equiv.), I0-1 (2.20 equiv.), tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 (0.04 equiv., CAS: 14221-01-3), and potassium carbonate (K2CO3, 4.00 equiv.) are stirred in dioxane:water (4:1 volume ratio) at 110 °C overnight under a nitrogen atmosphere. After cooling to room temperature (RT), the reaction mixture is extracted with DCM 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 product I1 as a solid. Instead of the boronic ester, the corresponding boronic acid can be used.

[0264] General procedure for synthetic AAV2: JPEG0007791176000045.jpg33101 I1 (1.00 equiv.) and liquid bromine (4.0 equiv., CAS 7726-95-6) are stirred in anhydrous dimethylformamide (DMF) under a nitrogen atmosphere overnight at room temperature. The reaction mixture is poured into water. The precipitate is filtered and washed with water and ethanol. The resulting crude product is purified by recrystallization or column chromatography to give product I2 as a solid.

[0265] General procedure for synthetic AAV3: [ka] where X H is a halogen selected from the group consisting of Cl, Br, and I. In certain embodiments, X H is Cl.

[0266] I2 (1.00 equiv.), I2-1 (2.20 equiv.), tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (0.02 equiv., CAS: 51364-51-3), and sodium tert-butoxide NaO tBu (4.00 equivalents, CAS: 865-48-5) is stirred in dry toluene under a nitrogen atmosphere. t Bu)3 (1M in toluene, 0.08 equivalents, CAS 13716-12-6) is added and the mixture is stirred at 80 °C until completion. After cooling to room temperature (rt), the reaction mixture is extracted with DCM 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 product I3 as a solid.

[0267] General procedure for synthetic AAV4: [ka] where X H is a halogen selected from the group consisting of Cl, Br, and I. In certain embodiments, X H is Cl.

[0268] I3 (1.00 equiv.), bis(pinacolato)diboron (2.20 equiv., CAS 73183-34-3), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.05 equiv., CAS 72287-26-4), and potassium acetate (KOAc, 4.00 equiv., CAS 127-08-2) are stirred overnight at 100 °C under a nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with DCM 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 product I4 as a solid.

[0269] General procedure for synthetic AAV4: [ka] I4 (1.00 equiv.) and sodium periodate (4 equiv., CAS 7790-28-5) are dissolved in THF / water (4:1 volume ratio) under a nitrogen atmosphere. Hydrochloric acid (2 mol / L, 0.1 equiv.) is added, and the mixture is stirred at room temperature for 24 hours. The resulting reaction mixture is extracted with DCM 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 product I5 as a solid.

[0270] General procedure for synthetic AAV5: [ka] I5 (1.00 equiv.) is dissolved in chlorobenzene under a nitrogen atmosphere. Boron tribromide (4.00 equiv., CAS 10294-33-4) is added, and the mixture is stirred at 100 °C for 2 h. After cooling to room temperature (RT), water is added, and the resulting solid is filtered and washed with water and methanol. The resulting crude product is purified by recrystallization or column chromatography to give product I6 as a solid.

[0271] General procedure for synthetic AAV6: [ka] I6 (1.00 equiv.) is dissolved in chlorobenzene under a nitrogen atmosphere. At 0 °C, boron trichloride solution (1 M in heptane, 0.67 equiv., CAS 10294-34-5) is added, and the mixture is stirred at room temperature for 2 h. A solution of aryl Grignard reagent I6-1 (e.g., 1 M in THF, 6.00 equiv.) is added to the mixture at 0 °C. The reaction mixture is stirred at room temperature for 1 h. As a result, the reaction mixture is extracted with DCM 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 product P1 as a solid.

[0272] cyclic voltmeter The cyclic voltage and current are measured in dichloromethane, or a suitable solvent, and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) at a concentration of 10 -3 The 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).

[0273] 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.

[0274] photophysical measurements Sample pretreatment: spin coating Equipment: Spin150, SPS euro The sample concentration is 0.2 mg / ml dissolved in toluene / DCM.

[0275] Program: 7) 2000 U / min for 30 seconds. After coating, the film was dried at 70° C. for 1 minute.

[0276] Photoluminescence and phosphorescence spectroscopy For phosphorescence and fluorescence spectroscopy analysis, a Horiba fluorescence spectrometer "Fluoromax 4P" is used.

[0277] 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 preferable 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 the selected wavelength is selected by a Czerny-Turner monochromator, which is also used to set the specific emission wavelength. The sample emission is directed to a 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 a three-exponential function is applied to determine the transient decay lifetime of the delayed fluorescence. Specific lifetime τ i and the corresponding amplitude A i The delayed fluorescence lifetime τ is calculated by weighting it by DF is determined.

number

[0278] Photoluminescence quantum yield measurements For photoluminescence quantum yield (PLQY) measurements, an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using software U6039-05 version 3.6.0.

[0279] The emission maxima are given in nm, the quantum yields Φ are given in %, and the CIE coordinates are given as x,y values.

[0280] PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard.

[0281] 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule.

[0282] 3) Measurement The quantum yield is measured on a solution or film sample in a nitrogen atmosphere and is calculated using the following equation:

number

[0283] where n 光子 indicates the number of photons, and Int indicates the intensity.

[0284] Fabrication and characterization of optoelectronic devices Optoelectronic devices, particularly OLED devices, containing the organic molecules according to the present invention can also be produced 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%.

[0285] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance; similarly, LT80 corresponds to the time when the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the time when the measured luminance has decreased to 95% of the initial luminance.

[0286] Accelerated lifetime measurements are performed (e.g., applying increased current densities), e.g., 500 cd / m 2 In the present invention, the LT80 value is determined using the following formula:

number

[0287] Here, L0 denotes the initial luminance at the applied current density.

[0288] The value corresponds to the average of several pixels (typically 2-8) and the standard deviation among the pixels is provided.

[0289] HPLC-MS HPLC-MS analysis is performed on an Agilent HPLC (1260 series) equipped with an MS-detector (Thermo LTQ XL).

[0290] 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]

[0291] The following solvent mixtures containing 0.1% formic acid are used: [Table 2] From the analyte solution at a concentration of 0.5 mg / mL, an injection volume of 2 μL is taken for the measurement.

[0292] 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.

[0293] Example 1 [ka] TIFF0007791176000057.tif90170

[0294] Additional Examples of Organic Molecules of the Invention [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

Claims

1. Organic molecules, including: a first chemical moiety comprising the structure of Formula I; and 【Chemistry 1】 ...Chemical formula I two second chemical moieties comprising the structure of Formula II; 【Chemistry 2】 ...Chemical formula II where X is B and Y is N; R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ and R Ｘ independently in each occurrence, the attachment position of the single bond connecting said first chemical moiety to said second chemical moiety and R ＊ is selected from the group consisting of R ＊ is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, OPh (Ph = phenyl), SPh, CF ３ ,CN,F,SI(C １ -C ５ alkyl) ３ , Si(Ph) ３ , C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium (D), CN, CF ３ or substituted by F, C １ -C ５ Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ６ -C １８ aryl, This may optionally be one or more C １ -C ５ Alkyl substituents, Ph, CN, CF ３ or substituted by F, C ３ -C １７ heteroaryl, This may optionally be one or more C １ -C ５ Alkyl substituents, Ph, CN, CF ３ or substituted by F, N (C ６ -C １８ aryl) ２ , N (C ３ -C １７ Heteroaryl) ２ , N (C ３ -C １７ Heteroaryl) (C ６ -C １８ aryl), In Formula 2, the dotted line indicates the point of attachment of the second chemical moiety to the first chemical moiety; Z is a direct bond; o is 0, p is 0, R ２ is independently selected in each occurrence from the group consisting of: hydrogen, deuterium, N(R ５ ) ２ 、 OR ５ 、 Si(R ５ ) ３ 、 B(OR ５ ) ２ 、 OSO ２ R ５ 、 CF ３ 、 C.N., F. Br, I, C １ -C ４０ Alkyl, This means that one or more substituents R ５ optionally replaced by Here, one or more non-adjacent CH ２ The group is 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, SO ２ , N.R. ５ , O, S or CONR ５ optionally replaced by C １ -C ４０ Alkoxy, This means that one or more substituents R ５ optionally replaced by Here, one or more non-adjacent CH ２ The group is 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, SO ２ , N.R. ５ , O, S or CONR ５ optionally replaced by C １ -C ４０ thioalkoxy, This means that one or more substituents R ５ optionally replaced by Here, one or more non-adjacent CH ２ The group is 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, SO ２ , N.R. ５ , O, S or CONR ５ optionally replaced by C ２ -C ４０ alkenyl, This means that one or more substituents R ５ optionally replaced by Here, one or more non-adjacent CH ２ The group is 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, SO ２ , N.R. ５ , O, S or CONR ５ optionally replaced by C ２ -C ４０ Alkynyl, This means that one or more substituents R ５ optionally replaced by Here, one or more non-adjacent CH ２ The group is 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, SO ２ , N.R. ５ , O, S or CONR ５ optionally replaced by C ６ -C ６０ aryl, This means that one or more substituents R ５ optionally substituted with C ３ -C ５７ heteroaryl, This means that one or more substituents R ５ optionally replaced by R ５ is independently selected in each occurrence from the group consisting of: hydrogen, deuterium, N(R ６ ) ２ 、 OR ６ 、 Si(R ６ ) ３ 、 B(OR ６ ) ２ 、 OSO ２ R ６ 、 CF ３ 、 C.N., F. Br, I, C １ -C ４０ Alkyl, This means that one or more substituents R ６ optionally replaced by Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ optionally replaced by C １ -C ４０ Alkoxy, This means that one or more substituents R ６ optionally replaced by Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ optionally replaced by C １ -C ４０ thioalkoxy, This means that one or more substituents R ６ optionally replaced by Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ optionally replaced by C ２ -C ４０ alkenyl, This means that one or more substituents R ６ optionally replaced by Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ optionally replaced by C ２ -C ４０ Alkynyl, This means that one or more substituents R ６ optionally replaced by Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, SI(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ optionally replaced by C ６ -C ６０ aryl, This means that one or more substituents R ６ optionally substituted with C ３ -C ５７ heteroaryl, This means that one or more substituents R ６ optionally replaced by R ６ is independently selected in each occurrence from the group consisting of: Hydrogen, deuterium, OPh, SPh, CF ３ ,CN,F,Si(C １ -C ５ alkyl) ３ , Si(Ph) ３ , C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C １ -C ５ thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ２ -C ５ Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or substituted by F, C ６ -C １８ aryl, This may optionally be one or more C １ -C ５ substituted with alkyl substituents, C ３ -C １７ heteroaryl, This may optionally be one or more C １ -C ５ substituted with alkyl substituents, N (C ６ -C １８ aryl) ２ , N (C ３ -C １７ Heteroaryl) ２ , and N (C ３ -C １７ Heteroaryl) (C ６ -C １８ aryl), where: Adjacent substituents R ２ are optionally joined together to form an aryl or heteroaryl ring, which optionally contains one or more C １ -C ５ Alkyl substituents, deuterium, halogen, CN or CF ３ is replaced by R I and R ＩＩ , R ＩＩ and R ＩＩＩ ,and R ＩＶ and R Ｖ two adjacent substituents selected from the group consisting of: indicate the attachment points of the single bonds linking the first chemical moiety to the second chemical moiety to form a ring; R ＶＩ and R ＶＩＩ , R ＶＩＩ and R ＶＩＩＩ ,and R ＩＸ and R Ｘ Two adjacent substituents selected from the group consisting of indicate the attachment points of the single bonds connecting the first chemical moiety to the second chemical moiety to form a ring.

2. 10. The organic molecule of claim 1 comprising the structure of Formula Ia: 【Transformation 3】 ...Chemical formula Ia where m is 0, n is 0.

3. 10. The organic molecule of claim 1 comprising the structure of Formula Ib: 【Chemistry 4】 ...Chemical formula Ib where m is 0, n is 0.

4. R ＊ is, independently in each occurrence, selected from the group consisting of: Hydrogen, deuterium, Me, ｉ Pr, ｔ Bu, SiMe ３ , SiPh ３ , and Me, ｉ Pr, ｔ Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu and Ph.

5. R ２ is, independently in each occurrence, selected from the group consisting of: hydrogen, Me、 ｉ Pr、 ｔ Bu、CN、CF ３ , Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ Ph optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ carbazolyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ Pr, ｔ Bu, C.N., C.F. ３ and Ph, and N(Ph) ２ .

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

7. 7. The use according to claim 6, wherein the optoelectronic device is selected from the group consisting of: ・Organic light-emitting diode (OLED) ・Light-emitting electrochemical cells ・OLED sensor ・Organic diode ・Organic solar cells ・Organic transistor ・Organic field-effect transistor ・Organic laser - Down conversion element.

8. A composition comprising: (a) one or more organic molecules according to any one of claims 1 to 5; (b) one or more emitter and / or host materials different from the organic molecules; and (c) optionally, one or more dyes and / or one or more solvents.

9. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 5 or a composition according to claim 8.

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

11. A method for producing an optoelectronic device, in which an organic molecule according to any one of claims 1 to 5 or a composition according to claim 8 is used.

12. 12. A method for manufacturing an optoelectronic device according to claim 11, comprising processing the organic molecules by a vacuum evaporation method or from a solution.

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