Organic triazine-containing organic molecules, methods for producing organic molecules, uses of organic molecules, compositions containing organic molecules, optoelectronic devices containing organic molecules, and methods for producing optoelectronic devices

Abstract

The present invention relates in particular to an organic compound for application in optoelectronic devices. According to the invention, said organic compound comprises: a first chemical moiety having the structure of Formula I; and [Formula 1] JPEG2023534546000099.jpg10248 two second chemical moieties, each independently having the structure of Formula II; [chemical 2] JPEG2023534546000100.jpg4859 wherein said first chemical moiety is linked to each of said two second chemical moieties via a single bond; Where: T and V are R A and R 1 are independently selected from the group consisting of: W is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or R A and R 2 is selected from the group consisting of X is a single bond attachment site linking the first chemical moiety to one of the two second chemical moieties, or R 2 and Y is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or R 2 and R T and R V is a single bond attachment site linking the first chemical moiety to one of the two second chemical moieties; R T and R V Another substituent selected from is CN and CF 3 is selected from the group consisting of R W is R I and R X is R I and R Y is RI It is.

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

[0004] The organic molecules of the present invention are purely organic molecules, ie they do not contain any metal ions, in contrast to the metal complexes known to be used in optoelectronic devices. [Effects of the Invention]

[0005] The organic molecules exhibit emission maxima in the sky blue, green, or yellow spectral range. The organic molecules exhibit emission maxima, particularly in the range of 490-600 nm, preferably 510-560 nm, and more preferably 520-540 nm. The photoluminescence quantum yield of the organic molecules according to the present invention is, in particular, 10% or more. The molecules according to the present invention in particular exhibit thermally activated delayed fluorescence (TADF). The use of the molecules according to the present invention in optoelectronic devices, such as organic light-emitting diodes (OLEDs), leads to higher device efficiencies. The corresponding OLEDs have higher stability than known emitter materials and OLEDs with similar hues, and / or, when the molecules according to the present invention are used in OLED displays, a more accurate reproduction of natural-looking hues, i.e., a higher resolution of the displayed image, is achieved. In particular, the molecules can be used in combination with fluorescent emitters to enable so-called hyperfluorescence. [Brief explanation of the drawings]

[0006] [Figure 1] 1 shows the emission spectrum of Example 1 (10 wt %) in PMMA. DETAILED DESCRIPTION OF THE INVENTION

[0007] 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] two second chemical moieties each independently comprising or consisting of the structure of formula II; [ka] wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond.

[0008] T is R A and R 1 is selected from the group consisting of:

[0009] V is R A and R 1 is selected from the group consisting of:

[0010] W is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or R A and R 2 is selected from the group consisting of:

[0011] X is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or R 2 is.

[0012] Y is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or R 2 is.

[0013] R A is a group consisting of two substituents R Tz and 1,3,5-triazinyl substituted with

[0014] [ka] , which is attached to the structure of Formula I via the position indicated by the dotted line.

[0015] R T is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or is selected from the group consisting of CN and CF3.

[0016] R V is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties, or is selected from the group consisting of CN and CF3.

[0017] R W is R I is.

[0018] R X is R I is.

[0019] R Y is R I is.

[0020] # indicates a single bond attachment site linking said second chemical moiety to said first chemical moiety.

[0021] Z, in each occurrence, independently, is a direct bond, CR 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3, N.R. 3 , O, SiR 3 R 4 , S, S(O) and S(O)2.

[0022] R 1 are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, C1-C5 alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C2-C8 alkenyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C2-C8 alkynyl, wherein one or more hydrogen atoms are selectively replaced by deuterium, and C6-C 18 aryl, This is a group consisting of one or more substituents R 6 is selectively substituted with

[0023] R 2 are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, C1-C5 alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C2-C8 alkenyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C2-C8 alkynyl, wherein one or more hydrogen atoms are selectively replaced by deuterium, and C6-C 18 aryl, This is a group consisting of one or more substituents R 6 is selectively substituted with

[0024] R I are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, C1-C5 alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C2-C8 alkenyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C2-C8 alkynyl, wherein one or more hydrogen atoms are selectively replaced by deuterium, and C6-C 18 aryl, This is a group consisting of one or more substituents R 6 is selectively substituted with

[0025] R Tz are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, C1-C5 alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C6-C 18 aryl, This is a group consisting of one or more substituents R 6 is optionally substituted with, and C3-C 17 heteroaryl, This is a group consisting of one or more substituents R 6 is selectively substituted with

[0026] R a , R 3 and R 4 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R 5 )2, OR 5 , Si(R 5 )3, B(OR 5 )2, OSO2R 5 , CF3, CN, F, Br, I, C1-C 40 Alkyl, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C1-C 40 Alkoxy, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C1-C 40 thioalkoxy, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C2-C 40 alkenyl, This is a group consisting of one or more substituents R 5 is selectively substituted with where one or more non-adjacent CH groups are R5 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 is selectively substituted by C2-C 40 Alkynyl, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C6-C 60 aryl, This is a group consisting of one or more substituents R 5 is optionally substituted with, and C3-C 57 heteroaryl, This is a group consisting of one or more substituents R 5 is selectively substituted with

[0027] R 5 are, in each occurrence, independently selected 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 is selectively substituted with 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 is selectively substituted by C1-C 40 Alkoxy, This is a group consisting of one or more substituents R 6 is selectively substituted with 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 is selectively substituted by C1-C 40 thioalkoxy, This is a group consisting of one or more substituents R 6 is selectively substituted with 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 is selectively substituted by C2-C 40 alkenyl, This is a group consisting of one or more substituents R 6 is selectively substituted with 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 is selectively substituted by C2-C 40 Alkynyl, This is a group consisting of one or more substituents R 6 is selectively substituted with 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 is selectively substituted by C6-C 60 aryl, This is a group consisting of one or more substituents R 6 is optionally substituted with, and C3-C 57 heteroaryl, This is a group consisting of one or more substituents R 6 is selectively substituted with

[0028] R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh (Ph = phenyl), CF3, CN, F, C1-C5 alkyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3, or F; C1-C5 alkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3, or F; C1-C5 thioalkoxy, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3, or F; C2-C5 alkenyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3, or F; C2-C5 alkynyl, wherein optionally one or more hydrogen atoms are replaced, independently of one another, by deuterium, CN, CF3, or F; C6-C 18 aryl, This can be one or more C1-C5 alkyl or C6-C 18 optionally substituted with aryl substituents; C3-C 17 heteroaryl, This can be one or more C1-C5 alkyl or C6-C 18 optionally substituted with aryl substituents; N(C6-C 18 aryl)2, N(C3-C 17 heteroaryl)2, and N(C3-C 17 Heteroaryl)(C6-C 18 aryl). Substituent R a , R 3 , R 4 or R 5 are, independently of one another, one or more substituents R a , R 3 , R 4 or R 5 and selectively form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system.

[0029] According to the present invention, exactly one substituent selected from the group consisting of T, V and W is present in R Awherein exactly one substituent selected from the group consisting of W, Y, and X represents a single bond attachment site connecting said first chemical moiety to one of said two second chemical moieties; and R T and R V and R T and R V Exactly one substituent selected from is selected from the group consisting of CN and CF3.

[0030] In one embodiment of the present invention, the first chemical moiety comprises or consists of the structure of Formula Ia: [ka] where R 1 , R 2 , R I and R Tz is defined as above, X D is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties; where R D is a single bond attachment site linking said first chemical moiety to one of said two second chemical moieties.

[0031] In one embodiment, R 1 , R 2 and R I are each independently selected from the group consisting of hydrogen (H), methyl, mesityl, tolyl and phenyl. The term tolyl denotes 2-tolyl, 3-tolyl and 4-tolyl.

[0032] In one embodiment, R 1 , R 2 and R I are, in each occurrence, independently selected from the group consisting of hydrogen (H), methyl, and phenyl.

[0033] In one embodiment, W is R A is.

[0034] In one embodiment, T is R A is.

[0035] In one embodiment, V is R A is.

[0036] In one embodiment, R T is CN.

[0037] In one embodiment, R T is CF3.

[0038] In one embodiment, R V is CN.

[0039] In one embodiment, R V is CF3.

[0040] In one embodiment, W is R A and R T is CN.

[0041] In one embodiment, W is R A and R T is CF3.

[0042] In one embodiment, W is R A and R V is CN.

[0043] In one embodiment, W is R A and R V is CF3.

[0044] In one embodiment, T is R A and R T is CN.

[0045] In one embodiment, T is R A and R Tis CF3.

[0046] In one embodiment, T is R A and R V is CN.

[0047] In one embodiment, T is R A and R V is CF3.

[0048] In one embodiment, V is R A and R T is CN.

[0049] In one embodiment, V is R A and R T is CF3.

[0050] In one embodiment, V is R A and R V is CN.

[0051] In one embodiment, V is R A and R V is CF3.

[0052] In a further embodiment of the present invention, R Tz are, in each occurrence, independently selected from the group consisting of: H, methyl, one or more substituents R 6 phenyl optionally substituted with one or more substituents R 6 1,3,5-triazinyl optionally substituted with one or more substituents R 6 pyridinyl optionally substituted with one or more substituents R 6 Pyrimidinyl optionally substituted with

[0053] In a further embodiment of the present invention, R Tzare each independently selected from the group consisting of H, methyl, and phenyl, where the phenyl substituents are further substituted with nitrile groups and carbazolyl groups, which are again substituted with one or more phenyl substituents.

[0054] In a further embodiment of the present invention, R Tz is phenyl in each instance.

[0055] In one embodiment of the present invention, R 3 , R 4 , R 5 and R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, halogens, CN, CF3, SiMe3, SiPh3, C1-C5 alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C6-C 18 aryl, wherein one or more hydrogen atoms are independently C1-C5 alkyl, C6-C 18 Aryl, C3-C 17 optionally substituted by heteroaryl, CN or CF; C3-C 15 heteroaryl, wherein one or more hydrogen atoms are independently C1-C5 alkyl, C6-C 18 Aryl, C3-C 17 optionally substituted by heteroaryl, CN, or CF3, and N(Ph)2.

[0056] In another embodiment of the present invention, R 3 , R 4 , R 5 and R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, halogens, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, and C6-C 18 aryl, wherein one or more hydrogen atoms are independently optionally replaced by C1-C5 alkyl, CN, CF3, and Ph.

[0057] In one embodiment of the present invention, R 3 , R 4 , R 5 and R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, halogens, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, and phenyl, wherein one or more hydrogen atoms are independently optionally replaced by C1-C5 alkyl, CN, CF3, and Ph.

[0058] In another embodiment of the present invention, R 3 , R 4 , R 5 and R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, halogens, Me, i Pr, t Bu, CN, CF3, SiMe3, SiPh3, and phenyl, wherein one or more hydrogen atoms are independently Me, i Pr, t Selectively substituted by Bu, CN, CF3 and Ph.

[0059] In a further embodiment of the invention, each of the two second chemical moieties, in each instance independently of each other, comprises or consists of a structure of the following formula IIa: [ka] where # and R a is defined as above.

[0060] In a further embodiment of the present invention, R a are, in each occurrence, independently selected from the group consisting of: H, 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 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.

[0061] In a further embodiment of the present invention, R a are, in each occurrence, independently selected from the group consisting of: H, Me, i Pr, t Bu, CN, CF3, Me, i Pr, tPh optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3 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, and Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0062] In a further embodiment of the present invention, R a are, in each occurrence, independently selected from the group consisting of: H, Me, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; and Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0063] In a further embodiment of the present invention, R a is H in each case.

[0064] In a further embodiment of the invention, each of the two second chemical moieties comprises or consists, in each instance independently of one another, of the structure of formula IIb, the structure of formula IIb-2, the structure of formula IIb-3 or the structure of formula IIb-4: [ka] Chemical formula IIb [ka] Chemical formula IIb-2 [ka] Chemical formula IIb-3 [ka] Chemical formula IIb-4 where: R b are, in each occurrence, independently selected from the group consisting of: deuterium, N(R 5 )2, OR 5 , Si(R 5 )3. B(OR 5 )2, OSO2R 5 , CF3, CN, F, Br, I, C1-C 40 Alkyl, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C1-C 40Alkoxy, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C1-C 40 thioalkoxy, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C2-C 40 alkenyl, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C2-C 40 Alkynyl, This is a group consisting of one or more substituents R 5 is selectively substituted with 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 is selectively substituted by C6-C 60 aryl, This is a group consisting of one or more substituents R 5 is optionally substituted with, and C3-C 57 heteroaryl, This is a group consisting of one or more substituents R 5 is selectively substituted with

[0065] The above definitions also apply.

[0066] In a further embodiment of the invention, each of the two second chemical moieties comprises or consists, in each instance independently of one another, of the structure of formula IIc, the structure of formula IIc-2, the structure of formula IIc-3 or the structure of formula IIc-4: [ka] chemical formula c [ka] Chemical formula c-2 [ka] Chemical formula c-3 [ka] Chemical formula c-4 Here, the above definitions apply.

[0067] In a further embodiment of the present invention, R b are, in each occurrence, independently selected from the group consisting of: 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.

[0068] In a further embodiment of the present invention, R b are, in each occurrence, independently selected from the group consisting of: 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, and Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0069] In a further embodiment of the present invention, R b are, in each occurrence, independently selected from the group consisting of: Me, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph; and Me, i Pr, t Triazinyl optionally substituted with one or more substituents independently selected from the group consisting of Bu, CN, CF3, and Ph.

[0070] The following are examples of the second chemical moiety:

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] [ka]

[0076] [ka]

[0077] [ka]

[0078] [ka]

[0079] [ka] where #, Z, R a , R 3 , R 4 and R 5 The above definitions apply.

[0080] In one embodiment, R a and R 5 are in each case independently of one another hydrogen (H), methyl (Me), i-propyl (CH(CH3)2)( i Pr), t-butyl ( t phenyl (Ph), CN, CF3, and diphenylamine (NPh2).

[0081] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula III:

[0082] [ka] where R Z is selected from the group consisting of CN and CF3; Apart from that, the above definitions apply.

[0083] In a further embodiment of the invention, the organic molecule comprises or consists of the structure of formula III-1 or III-2:

[0084] [ka]

[0085] [ka]

[0086] Here, the above definitions apply.

[0087] In a preferred embodiment of the invention, the organic molecule comprises or consists of the structure of formula III-1:

[0088] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula IIIa-1 or IIIa-2:

[0089] [ka]

[0090] [ka]

[0091] where: R c are, in each occurrence, independently selected from the group consisting of: Me, i Pr, t Bu, Me, i Pr, t Ph optionally substituted with one or more substituents independently selected from the group consisting of Bu, 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 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.

[0092] In a preferred embodiment of the invention, the organic molecule comprises or consists of the structure of formula IIIa-1:

[0093] In a further embodiment of the invention, the organic molecule comprises or consists of the structure of formula IIIb-1 or formula IIIb-2:

[0094] [ka]

[0095] [ka]

[0096] Here, the above definitions apply.

[0097] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula IIIb-1:

[0098] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula IIIc-1 or IIIc-2:

[0099] [ka]

[0100] [ka]

[0101] Here, the above definitions apply.

[0102] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula IIIc-1:

[0103] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula IIId-1 or IIId-2:

[0104] [ka]

[0105] [ka]

[0106] Here, the above definitions apply.

[0107] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula IIId-1:

[0108] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula IV:

[0109] [ka]

[0110] Here, the above definitions apply.

[0111] In a further embodiment of the invention, the organic molecule comprises or consists of the structure of formula IV-1 or IV-2:

[0112] [ka]

[0113] [ka]

[0114] Here, the above definitions apply.

[0115] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula IV-1:

[0116] In a further embodiment of the invention, the organic molecule comprises or consists of the structure of formula IVa-1 or IVa-2:

[0117] [ka]

[0118] [ka]

[0119] Here, the above definitions apply.

[0120] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula IVa-1:

[0121] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula IVb-1 or IVb-2:

[0122] [ka]

[0123] [ka]

[0124] Here, the above definitions apply.

[0125] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula IVb-1:

[0126] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula V:

[0127] [ka]

[0128] Here, the above definitions apply.

[0129] In a further embodiment of the invention, the organic molecule comprises or consists of a structure of formula V-1 or V-2:

[0130] [ka]

[0131] [ka]

[0132] Here, the above definitions apply.

[0133] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula V-1:

[0134] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula VI:

[0135] [ka]

[0136] Here, the above definitions apply.

[0137] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula VI, wherein

[0138] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula VII:

[0139] [ka]

[0140] Here, the above definitions apply.

[0141] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula VII, wherein

[0142] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula VIII:

[0143] [ka]

[0144] Here, the above definitions apply.

[0145] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula VIII, wherein

[0146] In one embodiment of the present invention, the organic molecule comprises or consists of the structure of Formula IX:

[0147] [ka]

[0148] Here, the above definitions apply.

[0149] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula IX, wherein

[0150] In one embodiment of the invention, the organic molecule comprises or consists of a structure of formula X:

[0151] [ka]

[0152] Here, the above definitions apply.

[0153] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula X, where

[0154] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula XI:

[0155] [ka]

[0156] Here, the above definitions apply.

[0157] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula XI, wherein

[0158] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula XII:

[0159] [ka]

[0160] Here, the above definitions apply.

[0161] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula XII, wherein

[0162] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula XIII:

[0163] [ka]

[0164] Here, the above definitions apply.

[0165] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula XIII, wherein

[0166] In one embodiment of the invention, the organic molecule comprises or consists of the structure of formula XIV:

[0167] [ka]

[0168] Here, the above definitions apply.

[0169] In another embodiment of the invention, the organic molecule is R Z The compound may comprise or consist of a structure of formula XIV, wherein

[0170] As used throughout this specification, the terms "aryl" and "aromatic" are understood in the broadest sense to refer to any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms. A heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this specification, the number of aromatic ring atoms may be given in subscript numerals in the definitions of specific substituents. In particular, a heteroaromatic ring contains 1 to 3 heteroatoms.

[0171] Furthermore, the terms "heteroaryl" and "heteroaromatic" are understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety containing at least one heteroatom. The heteroatom, in each case, may be the same or different and may be independently selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent that possesses two bonding sites and serves as a linker structure to other molecular structures. In exemplary embodiments, if a group is defined differently from the definitions given herein, for example, if the number of aromatic ring atoms or heteroatoms differs from the definitions given, the definitions in the exemplary embodiments apply. 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 a polycycle via a condensation reaction.

[0172] 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.

[0173] As used throughout this specification, the term "cyclic group" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0174] As used throughout this specification, the term "biphenyl" is also understood in its broadest sense as a substituent to refer to ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined in relation to the point of attachment to another chemical moiety.

[0175] As used throughout this specification, the term "alkyl group" is understood in the broadest sense to include 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 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.

[0176] 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.

[0177] 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.

[0178] 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.

[0179] 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.

[0180] The terms "halogen" and "halo" as used throughout this specification are also understood in the broadest sense, preferably fluorine, chlorine, bromine or iodine.

[0181] Wherever hydrogen (H) is mentioned herein, it is also substituted with deuterium in each instance.

[0182] 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.

[0183] In one embodiment, in a poly(methyl methacrylate) (PMMA) film containing 10 wt. % organic molecules at room temperature, the organic molecules according to the present invention have an excited state lifetime of 25 μs or less, 15 μs or less, particularly 10 μs or less, more preferably 8 μs or less, or 6 μs or less, and even more preferably 4 μs or less.

[0184] In one embodiment of the present invention, the organic molecule according to the present invention exhibits a thermally activated delayed fluorescence (TADF) emitter, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1), ΔE ST value, which is 5000 cm -1 less than, preferably, 3000 cm -1 less than, more preferably, 1500 cm -1 less than, even more preferably, 1000 cm -1 Less than, or preferably, 500 cm -1 has a value less than

[0185] In a further embodiment of the present invention, in a PMMA film containing 10 wt. % of organic molecules at room temperature, the organic molecules according to the present invention have an emission peak in the visible or near-ultraviolet range, i.e., in the wavelength range of 380 nm to 800 nm, with a full width at half maximum value of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or less than 0.40 eV.

[0186] Orbital energies and excited state energies can be determined through experimental methods and computational methods using quantum chemical methods, particularly density functional theory calculations. The highest occupied molecular orbital energy, E HOMO is determined to an accuracy of 0.1 eV from cyclic voltammetry measurements by methods known to those skilled in the art. LUMO is E HOMO +E gap where E gapis determined as follows: for host compounds, unless otherwise specified, the onset of the emission spectrum of a PMMA film containing 10 wt % of the host is E gap For the emitter molecule, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film containing 10% by weight of the emitter intersect. For the organic molecules according to the invention, E gap is determined as the energy at which the excitation and emission spectra of a PMMA film containing 10 wt % of the emitter intersect.

[0187] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperatures, typically 77 K. For host compounds where the first excited singlet state and the lowest triplet state are energetically separated by 0.4 eV or more, phosphorescence is typically visible in the steady-state spectrum in 2-Me-THF. Therefore, the triplet energy is also determined as the onset of the phosphorescence spectrum. For TADF emitter molecules, the energy of the first excited triplet state T1 is determined from the onset of the delayed emission spectrum at 77 K, measured in a PMMA film containing 10 wt. % of the emitter, unless otherwise specified. For both the host and emitter compounds, the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum (measured as follows: TADF emitter: 10 wt. % concentration in PMMA film; host: pure film).

[0188] The onset of the emission spectrum is determined by calculating the intersection of a tangent to the emission spectrum with the x-axis, which is set at the high energy side of the emission band and at half maximum of the maximum intensity of the emission spectrum. A further aspect of the present invention relates to a method for preparing an organic molecule according to the present invention (including selective subsequent reactions), wherein reactants selected from the group consisting of 2-bromo-6-fluorobenzonitrile, 3-bromo-2-fluorobenzonitrile, 1-bromo-3-fluoro-2-(trifluoromethyl)benzene and 1-bromo-2-fluoro-3-(trifluoromethyl)benzene are used, wherein each of the reactants contains exactly three substituents R I is selectively substituted with

[0189] [ka]

[0190] [ka]

[0191] According to the present invention, boronic acids or equivalent boronic acid esters can be used in place of the pinacol boronic acid esters.

[0192] In the nucleophilic aromatic substitution reaction of nitrogen heterocycles with aryl halides, preferably aryl fluorides, typical conditions involve the use of a base such as potassium phosphate or sodium hydride in an aprotic polar solvent such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF).

[0193] An alternative synthetic route involves the introduction of the nitrogen heterocycle to an aryl halide or aryl pseudohalide, preferably an aryl bromide, aryl iodide, aryl triflate or aryl tosylate, via copper or palladium catalyzed coupling.

[0194] A further aspect of the present invention relates to the use of organic molecules according to the 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.

[0195] An optoelectronic device, also called organic 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.

[0196] In connection with such applications, the optoelectronic device is more particularly selected from the group consisting of:

[0197] -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 -Downward conversion element For such applications, in preferred embodiments, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light emitting transistor.

[0198] In one embodiment, the light-emitting layer of an organic light-emitting diode comprises organic molecules according to the invention. In this case, in an optoelectronic device, in particular an OLED, the proportion of organic molecules according to the invention in the light-emitting layer is 1% to 99% by weight, or even 5% to 80% by weight. In an alternative embodiment, the proportion of organic molecules in the light-emitting layer is 100% by weight.

[0199] 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.

[0200] A further aspect of the present invention relates to a composition comprising or consisting of:

[0201] (a) one or more organic molecules according to the invention, in particular in emitter and / or host form; (b) one or more emitter and / or host materials different from the organic molecules according to the present invention; (c) optionally, one or more dyes and / or one or more solvents In further embodiments of the present invention, the composition has a photoluminescence quantum yield (PLQY) at room temperature of greater than 10%, preferably greater than 20%, more preferably greater than 40%, even more preferably greater than 60%, or even more preferably greater than 70%.

[0202] In one embodiment, the light-emitting layer comprises a composition consisting of, comprising, or consisting essentially of:

[0203] (a) one or more organic molecules according to the invention, in particular in emitter and / or host form; (b) one or more emitter and / or host materials different from the organic molecules according to the present invention; (c) optionally, one or more dyes and / or one or more solvents Particularly preferably, the light-emitting layer EML comprises a composition consisting of or comprising (or consisting essentially of):

[0204] (i) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules E according to the invention (ii) 5 to 99% by weight, preferably 30 to 94.9% by weight, in particular 40 to 89% by weight, of one or more host compounds H (iii) optionally 0 to 94% by weight, preferably 0.1 to 65% by weight, in particular 1 to 50% 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; (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; The ingredients or compositions are selected so that the sum of the weights of the ingredients adds up to 100%.

[0205] Preferably, energy is transferred from the host compound H to one or more organic molecules E according to the present 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 present 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 present invention.

[0206] In a further embodiment, the emissive layer EML comprises a composition consisting of or comprising (or consisting essentially of):

[0207] (i) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one organic molecule E according to the invention (ii) 5 to 99% by weight, preferably 30 to 94.9% by weight, in particular 40 to 89% by weight, of one host compound H (iii) optionally 0 to 94% by weight, preferably 0.1 to 65% by weight, in particular 1 to 50% by weight, of 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; (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; 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).

[0208] 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).

[0209] In one embodiment, the host compound H has an energy E HOMO Highest occupied molecular orbital HOMO (H) with (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 Highest occupied molecular orbital HOMO (D) with 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 Highest occupied molecular orbital (HOMO) with (E) and energy E LUMO (E) having a lowest unoccupied molecular orbital (LUMO) (E), where: E HOMO (H)>E HOMO (D), and the energy level of the highest occupied molecular orbital (HOMO) (E) of the organic molecule E according to the present invention (E HOMO (E)) and the energy level of the highest occupied molecular orbital (HOMO) of the host compound H (E HOMO (H)) is −0.5 eV to 0.5 eV, more preferably −0.3 eV to 0.3 eV, even more preferably −0.2 eV to 0.2 eV, or even more preferably −0.1 eV to 0.1 eV, E LUMO (H)>E LUMO (D), and the energy level of the lowest unoccupied molecular orbital (LUMO) (E) of the organic molecule E according to the present invention (E LUMO(E)) and the energy level of the lowest unoccupied molecular orbital (LUMO) (D) of at least one additional host compound D (E LUMO The difference from (D)) is −0.5 eV to 0.5 eV, more preferably −0.3 eV to 0.3 eV, even more preferably −0.2 eV to 0.2 eV, or even more preferably −0.1 eV to 0.1 eV.

[0210] 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 an organic light emitting diode (OLED), a light emitting electrochemical cell, an OLED sensor, in particular a gas sensor and a vapor sensor that are not completely sealed off from the outside, an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a downward conversion device.

[0211] 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.

[0212] In one embodiment of the inventive optoelectronic device, the inventive organic molecule E is used as emissive material in the emissive layer EML.

[0213] 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.

[0214] When the optoelectronic device is an OLED, it can have, for example, the following layer structure:

[0215] 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer Here, the OLED may optionally include each layer, different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0216] 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.

[0217] In one embodiment of the present invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0218] 1. Substrate 2. Cathode layer 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Emitting layer B 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A Here, an OLED having an inverted layer structure may optionally include each layer, and different layers may be combined, and the OLED may also include one or more layers of each layer type defined above.

[0219] 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 side-by-side arrangement of OLEDs. 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.

[0220] 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. Optionally, additional layers such as charge generation layers, charge blocking layers, or charge transport layers may be included between the individual 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 two light-emitting layers. Adjacent light-emitting layers or light-emitting layers separated by a charge generation layer may also be merged.

[0221] 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.

[0222] 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).

[0223] 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.

[0224] 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).

[0225] 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.

[0226] 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.

[0227] 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 can also be doped with a material such as Liq. The electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0228] 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).

[0229] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca, or Al. Alternatively, or in addition, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscale silver wires.

[0230] The OLED optionally further includes 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 include lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li2O, BaF2, MgO, and / or NaF.

[0231] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds H.

[0232] 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 optionally also be TADF emitters. Alternatively, the emitter molecules F may optionally 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 emitter molecules according to the present invention to the emitter molecules F before relaxing to the ground state S, typically emitting light that is red-shifted compared to the light emitted by the 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).

[0233] Optionally, the optoelectronic device (e.g., OLED) may also be, for example, essentially a white optoelectronic device. For example, such a white optoelectronic device may comprise at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Optionally, there may then be energy transfer between the two or more molecules, as described above.

[0234] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: wavelength range of >380~420nm Deep blue: wavelength range of >420~480nm Sky blue: wavelength range of >480~500nm Green: wavelength range of >500~560nm Yellow: wavelength range of >560-580nm Orange: wavelength range of >580~620nm Red: wavelength range of >620~800nm Associated with the emitter molecule, such hues exhibit emission maxima. Thus, for example, a deep blue emitter has an emission maximum in the >420-480 nm range, a sky blue emitter has an emission maximum in the >480-500 nm range, a green emitter has an emission maximum in the >500-560 nm range, and a red emitter has an emission maximum in the >620-800 nm range.

[0235] 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.

[0236] A further embodiment of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (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-emitting (top electrode transparent) devices, the test device used throughout this invention refers to a bottom-emitting device (bottom electrode and substrate transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates 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, or even more preferably 0.12 to 0.22, and / or CIEy color coordinates of 0.14 to 0.19, and / or 0.44 to 0.84, preferably 0.55 to 0.83, more preferably 0.65 to 0.82, even more preferably 0.70 to 0.81, or even more preferably 0.75 to 0.8.

[0237] Therefore, a further aspect of the present invention is a method for manufacturing a 14500 cd / m 2 an OLED that exhibits an external quantum efficiency of greater than 10%, more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 17%, or even more preferably greater than 20% at 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; and / or an OLED that exhibits an external quantum efficiency of greater than 14500 cd / m 2The present invention relates to OLEDs that exhibit LT97 values ​​of greater than 100 h, preferably greater than 200 h, more preferably greater than 400 h, even more preferably greater than 750 h, or even greater than 1000 h.

[0238] Yet another aspect of the present invention relates to OLEDs that emit light at well-defined color points. According to the present invention, the OLEDs emit light having a narrow emission bandwidth (small full width at half maximum (FWHM)). In one aspect, the OLEDs according to the present invention emit light with a FWHM of the main emission peak of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even more preferably less than 0.40 eV.

[0239] In a further aspect, the present invention relates to a method for producing an optoelectronic component, in which the organic molecule of the present invention is used.

[0240] 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.

[0241] 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.

[0242] 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., nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art.

[0243] [Example] General Synthesis Method I [ka]

[0244] General Synthesis Method II [ka]

[0245] General procedure for synthetic AAV1 [ka]

[0246] 4-Chloro-2-fluorophenylboronic acid ester (1.10 equiv.), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.00 equiv.), Pd(dppf)Cl ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)], 0.03 equiv.), and potassium carbonate (2.50 equiv.) were stirred in a 9:1 dioxane / water mixture at 100 °C for 16 h under a nitrogen atmosphere. The resulting crude product was precipitated from water, filtered, and washed with ethanol. Product I1-0 was obtained as a solid.

[0247] In the subsequent reaction, I1-0 (1.00 equiv.), bis(pinacolato)diboron (1.50 equiv.), Pd(dppf)Cl2 ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)], 0.05 equiv.), and potassium acetate (6.00 equiv.) were stirred in toluene under a nitrogen atmosphere at 110 °C for 20 h. The reaction mixture was then cooled to room temperature and extracted with ethyl acetate and water. The combined organic phases were dried over MgSO4, and the solvent was evaporated under reduced pressure. The resulting crude product was dissolved in toluene, passed through a short silica column, and the solvent was evaporated. The resulting solid was heated under reflux with ethanol for 2 h. The product was filtered hot to give I1 as a solid.

[0248] In the subsequent reaction, I1 (1.00 equiv.), 2-bromo-6-fluorobenzonitrile (1.20 equiv.), Pd(dppf)Cl2 ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)], 0.05 equiv.), and potassium carbonate (2.00 equiv.) were stirred in a toluene / dioxane / water mixture (5:5:1 ratio) at 110 °C for 16 h under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature. The precipitated crude product was filtered and washed with a mixture of water and methanol. The combined crude products were heated under reflux with ethanol for 1 h. The hot product was filtered and washed with ethanol to give Z1 as a solid.

[0249] General procedure for synthetic AAV2 [ka]

[0250] Z1 (1.00 equiv.), the corresponding donor molecule DH (2.20 equiv.), and tripotassium phosphate (5.00 equiv.) were suspended in DMSO under a nitrogen atmosphere and stirred at 120 °C for 20 h. The reaction mixture was then poured into a stirred mixture of water and ice. The precipitate was filtered and washed with water and cold ethanol. The resulting crude product was heated under reflux with ethyl acetate for 2 h. The product was hot filtered and washed with ethanol. It was obtained as a solid.

[0251] In particular, the donor molecule DH can be selected from 3,6-substituted carbazoles (e.g., 3,6-dimethylcarbazole, 3,6-diphenylcarbazole, 3,6-di-tert-butylcarbazole), 2,7-substituted carbazoles (e.g., 2,7-dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), 1,8-substituted carbazoles (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1 ,8-di-tert-butylcarbazole), 1-substituted carbazoles (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), 2-substituted carbazoles (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-tert-butylcarbazole), or 3-substituted carbazoles (e.g., 3-methylcarbazole, 3-phenylcarbazole, 3-tert-butylcarbazole).

[0252] Illustratively, halogen-substituted carbazoles, particularly 3-bromocarbazole, can be used as DH.

[0253] In a subsequent reaction, a boronic ester or boronic acid functional group can be introduced, for example, at the position of one or more halogen substituents introduced via DH, to generate the corresponding carbazol-3-ylboronic ester or carbazol-3-ylboronic acid, for example, via reaction with bis(pinacolato)diboron (CAS No. 73183-34-3). The corresponding halogenated reactant R a -Hal, preferably R a -Cl and R a In place of the boronic ester group or the boronic acid group, one or more substituents R a can be introduced.

[0254] Alternatively, one or more substituents R a is the substituent R a Boronic acid [R a-B(OH)2] or the corresponding boronic ester can be introduced at the position of one or more halogen substituents introduced via DH.

[0255] 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).

[0256] 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.

[0257] optical physical measurements Sample pretreatment: spin coating Equipment: Spin150, SPS euro The sample concentration is 10 mg / ml dissolved in an appropriate solvent.

[0258] Program: 1) 400 U / min for 3 seconds, 1000 U / min for 20 seconds (1000 U / m / s). 3) 4000 U / min for 10 seconds (1000 U / m / s). After coating, the film was dried at 70°C for 1 minute.

[0259] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC) Steady-state emission spectroscopy was recorded using a Model FluoroMax-4 (Horiba Scientific) equipped with a 150 W xenon-Arc lamp, excitation and emission monochromators, a Hamamatsu R928 photomultiplier tube, and time-correlated single-photon counting options. Standard correction fits were used to correct the emission and excitation spectra.

[0260] Excited state lifetimes are determined using the same system using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub.

[0261] Excitation light source: NanoLED 370 (wavelength: 371 nm, pulse duration: 1.1 ns) NanoLED 290 (wavelength: 294 nm, pulse duration: <1 ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm) Data analysis (exponential fit) is performed using the software suite DataStation and DAS6 analysis software. The fit is determined using the chi-squared test.

[0262] 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.

[0263] The emission maxima are given in nm, the quantum yields Φ are given in % and the CIE coordinates are given as x,y values.

[0264] PLQY is determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a standard. 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured on a solution or film sample in a nitrogen atmosphere and is calculated using the following equation:

[0265]

number

[0266] 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%.

[0267] 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 at which the measured luminance has decreased to 50% of the initial luminance; similarly, LT80 corresponds to the time at which the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the time at which the measured luminance has decreased to 95% of the initial luminance.

[0268] 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:

[0269]

number

[0270] Here, L0 denotes the initial luminance at the applied current density.

[0271] The value corresponds to the average of several pixels (typically 2-8) and the standard deviation among the pixels is provided.

[0272] HPLC-MS HPLC-MS analysis is performed on an Agilent HPLC (1100 series) equipped with an MS detector (Thermo LTQ XL). A reversed-phase column 4.6 mm x 150 mm, Waters particle size 5.0 μm (without pre-column) is used for the HPLC. HPLC-MS measurements are performed at room temperature (rt) using the following solvents: acetonitrile, water, and THF in the following concentrations:

[0273] [Table 1]

[0274] The following gradients are used:

[0275] [Table 2]

[0276] Ionization of the probe is accomplished by APCI (Atmospheric Pressure Chemical Ionization).

[0277] Example 1 [ka]

[0278] Example 1 was synthesized with AAV1 (41%) and AAV2 (quantitative yield).

[0279] [Table 3] Figure 1 shows the emission spectrum of Example 1 (10 wt% in PMMA). max The photoluminescence quantum yield (PLQY) is 68%, the full width at half maximum (FWHM) is 0.44 eV, and the emission lifetime is 16.6 μs. The CIEx coordinate is determined by 0.27, and the CIEy coordinate is determined by 0.49.

[0280] Example D1 Example 1 was tested on an optoelectronic device in the form of an OLED D1 manufactured with the following layer structure:

[0281] [Table 4]

[0282] [ka]

[0283] OLED D1 is 1000cd / m 2 It exhibits an external quantum efficiency (EQE) of 16.7% at 1200 cd / m. The emission maximum is 518 nm and the FWHM is 82 nm at 7.9 V. The corresponding CIEx value is 0.29 and CIEy value is 0.58. 2 The LT95 value was determined to be 42 hours.

[0284] Additional Examples of Organic Molecules of the Invention [ka]

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Claims

1. An organic molecule represented by the following chemical formula 1. 【Chemistry 1】 Chemical formula 1 Z in each occurrence independently represents a direct bond, CR ３ R ４ , C=CR ３ R ４ , C═O, C═NR ３ , N.R. ３ , O, SiR ３ R ４ , S, S(O) and S(O) ２ is selected from the group consisting of R a , R 3 and R 4 are, in each occurrence, independently of one another, selected 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 , C.F. ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This means that one or more substituents R ５ is selectively substituted with 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 is selectively substituted by C １ -C ４０ Alkoxy, This means that one or more substituents R ５ is selectively substituted with 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 is selectively substituted by C １ -C ４０ thioalkoxy, This means that one or more substituents R ５ is selectively substituted with 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 is selectively substituted by C ２ -C ４０ alkenyl, This means that one or more substituents R ５ is selectively substituted with 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 is selectively substituted by C ２ -C ４０ Alkynyl, This means that one or more substituents R ５ is selectively substituted with 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 is selectively substituted by C ６ -C ６０ aryl, This means that one or more substituents R ５ is optionally substituted with, and C ３ -C ５７ heteroaryl, This means that one or more substituents R ５ is selectively substituted with R ５ are, in each occurrence, independently selected 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 , C.F. ３ ,CN,F,Br,I, C １ -C ４０ Alkyl, This means that one or more substituents R ６ is selectively substituted with 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 is selectively substituted by C １ -C ４０ Alkoxy, This means that one or more substituents R ６ is selectively substituted with 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 is selectively substituted by C １ -C ４０ thioalkoxy, This means that one or more substituents R ６ is selectively substituted with 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 is selectively substituted by C ２ -C ４０ alkenyl, This means that one or more substituents R ６ is selectively substituted with 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 is selectively substituted by C ２ -C ４０ Alkynyl, This means that one or more substituents R ６ is selectively substituted with 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 is selectively substituted by C ６ -C ６０ aryl, This means that one or more substituents R ６ is optionally substituted with, and C ３ -C ５７ heteroaryl, This means that one or more substituents R ６ is selectively substituted with R ６ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh, CF ３ ,C.N.,F. 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 means that 1 or more C １ -C ５ Alkyl or C ６ -C １８ optionally substituted with aryl substituents; C ３ -C １７ heteroaryl, This means that 1 or more C １ -C ５ Alkyl or C ６ -C １８ optionally substituted with aryl 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) Here, the substituent R ａ or R ５ are, independently of one another, one or more substituents R ａ or R ５ and selectively form a monocyclic or polycyclic, aliphatic, aromatic and / or benzo-fused ring system.

2. An organic molecule represented by the following chemical formula IVa-1: 【Chemistry 2】 Here, R ＴＺ are independently selected from the group consisting of: hydrogen, deuterium, C １ -C ５ Alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C ６ -C １８ aryl, This means that one or more substituents R ６ is optionally substituted with, and C ３ -C １７ heteroaryl, This means that one or more substituents R ６ is selectively substituted with R ｃ are, in each occurrence, independently selected from the group consisting of: Me, ｉ Pr、 ｔ This, 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 pyrimidinyl 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, optionally substituted with one or more substituents independently selected from the group consisting of: N(Ph) ２ 、 R ６ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh, CF ３ ,C.N.,F. 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 means that 1 or more C １ -C ５ Alkyl or C ６ -C １８ optionally substituted with aryl substituents; C ３ -C １７ heteroaryl, This means that 1 or more C １ -C ５ Alkyl or C ６ -C １８ optionally substituted with aryl 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).

3. An organic molecule represented by the following chemical formula IVb-1: 【Transformation 3】 Here, R ＴＺ are independently selected from the group consisting of: hydrogen, deuterium, C １ -C ５ Alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C ６ -C １８ aryl, This means that one or more substituents R ６ is optionally substituted with, and C ３ -C １７ heteroaryl, This means that one or more substituents R ６ is selectively substituted with R ｃ are, in each occurrence, independently selected from the group consisting of: Me, ｉ Pr、 ｔ This, 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 pyrimidinyl 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, optionally substituted with one or more substituents independently selected from the group consisting of: N(Ph) ２ 、 R ６ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, OPh, CF ３ ,C.N.,F. 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 means that 1 or more C １ -C ５ Alkyl or C ６ -C １８ optionally substituted with aryl substituents; C ３ -C １７ heteroaryl, This means that 1 or more C １ -C ５ Alkyl or C ６ -C １８ optionally substituted with aryl 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).

4. R Ｔｚ are independently selected from the group consisting of H, methyl and phenyl, and at least one substituent R Ｔｚ is a phenyl group, it may be one or more substituents R ６ 4. The organic molecule of claim 2 or 3, substituted with:

5. 10. A method for preparing an organic molecule according to claim 1, comprising providing a reactant consisting of 2-bromo-6-fluorobenzonitrile, wherein all reactants contain exactly three substituents R Ｉ is replaced by The R Ｉ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, C １ -C ５ Alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C ２ -C ８ alkenyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C ２ -C ８ Alkynyl, wherein one or more hydrogen atoms are selectively replaced by deuterium, and C ６ -C １８ aryl, This means that one or more substituents R ６ A method for producing organic molecules selectively substituted with

6. 5. A method for producing an organic molecule according to any one of claims 2 to 4, comprising providing a reactant consisting of 3-bromo-2-fluorobenzonitrile, wherein the reactant contains exactly three substituents R Ｉ is replaced by The R Ｉ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, C １ -C ５ Alkyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C ２ -C ８ alkenyl, wherein one or more hydrogen atoms are selectively replaced by deuterium; C ２ -C ８ Alkynyl, wherein one or more hydrogen atoms are selectively replaced by deuterium, and C ６ -C １８ aryl, This means that one or more substituents R ６ A method for producing organic molecules selectively substituted with

7. Use of an organic molecule according to any one of claims 1 to 4 as a light emitter and / or host material and / or electron transport material and / or hole injection material and / or hole blocking material in an optoelectronic device.

8. 8. The use according to claim 7, 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 ・Downward conversion element.

9. A composition comprising: (a) one or more organic molecules according to any one of claims 1 to 4 in emitter and / or host form; (b) one or more emitter and / or host materials different from the organic molecules according to any one of claims 1 to 4, and (c) optionally, one or more dyes and / or one or more solvents.

10. 10. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 4 or a composition according to claim 9, and having the form of a device selected from the group consisting of organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, non-hermetic gas and vapor sensors, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and downward conversion devices.

11. -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 10 , wherein the light-emitting layer is disposed between the anode and the cathode and comprises the organic molecule or the composition.

12. 10. A method for manufacturing an optoelectronic device, wherein an organic molecule according to any one of claims 1 to 4 or a composition according to claim 9 is used, the method comprising processing said organic molecule by a vacuum evaporation method or from a solution.

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