Organic molecules for optoelectronic devices, uses of organic molecules, compositions, optoelectronic devices, and methods for manufacturing optoelectronic devices

Abstract

The present invention relates to organic molecules, particularly for application in optoelectronic devices. According to the present invention, the organic molecules have the structure of Formula I, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R A , R B , R C and R D However, hydrogen, deuterium, halogens, C 1 ~C 12 -alkyl, optionally with one or more hydrogen atoms being R 5 independently substituted by C 6 ~C 18 -aryl, optionally with one or more hydrogen atoms being R 5 and C 3 ~C 15 -heteroaryl, optionally with one or more hydrogen atoms being R 5 and R is independently selected from the group consisting of I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R A , R B , R C、 R D Any two adjacent rings may form a monocyclic ring system having 5 to 8 C atoms, and optionally each hydrogen may be independently selected from R 6 and at least R A and R B together form a monocyclic ring system having 5 to 8 C atoms. [Formula 1] JPEG2023511709000095.jpg4566 Formula I

Description

[Technical field]

[0001] The present invention relates to light-emitting 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] It is an object of the present invention to provide molecules suitable for use in optoelectronic devices. [Means for solving the problem]

[0003] This objective is achieved by the present invention, which provides novel organic molecules.

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

[0005] According to the invention, the organic molecules exhibit an emission maximum in the blue, sky blue or green spectral region. The organic molecules exhibit an emission maximum in particular between 420 nm and 520 nm, preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm. The photoluminescence quantum yield of the organic molecules according to the invention is in particular greater than 50%. The use of the molecules according to the invention in optoelectronic devices, such as for example organic light-emitting diodes (OLEDs), leads to a higher efficiency, expressed by the full width at half maximum (FWHM), or a higher color purity by the device. The corresponding OLEDs have a higher stability than OLEDs with known emitter materials and comparable colors. [Brief description of the drawings]

[0006] [Figure 1] FIG. 1 is the emission spectrum of Example 1 in PMMA (2% by weight). [Diagram 2] FIG. 2 is the emission spectrum of Example 2 in PMMA (2% by weight). [Diagram 3] FIG. 3 is the emission spectrum of Example 3 in PMMA (2% by weight). [Figure 4] FIG. 4 is the emission spectrum of Example 4 in PMMA (2% by weight). [Diagram 5] FIG. 5 is the emission spectrum of Example 5 in PMMA (2% by weight). [Figure 6] FIG. 6 is the emission spectrum of Example 6 in PMMA (2% by weight). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] The organic light-emitting molecules according to the present invention comprise or consist of the structure of Formula I: [ka] Formula I During the ceremony, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R A , R B , R C and R D but, Hydrogen, deuterium, halogens, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently selected from the group consisting of:

[0008] R 5 At each occurrence, Hydrogen, deuterium, halogens, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 6 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 6 independently substituted by C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 6 and independently selected from the group consisting of:

[0009] R 6 At each occurrence, Hydrogen, deuterium, halogens, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted with alkyl substituents.

[0010] Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R A , R B , R C、 R D any two adjacent groups independently form a monocyclic ring system having 5 to 8 C atoms (i.e. 5, 6, 7 or 8 carbon atoms, in particular 5 or 6 carbon atoms), Optionally, each hydrogen may be independently selected from R 6 can be replaced by:

[0011] R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R A , R B , R C , R D Any two adjacent ones of are, for example, R I and R II , R IIと R III、 R III and R IV , R IV and R V , R VI and R VII , R VII and R VIII , R A and R B , R C and R D And so on.

[0012] In particular, the term "monocyclic ring system" refers to a non-aromatic ring.

[0013] At least R A and RB together form a monocyclic ring system having 5, 6, 7 or 8 C atoms, Optionally, the hydrogens may be independently selected from R 6 can be replaced by:

[0014] Optionally, each hydrogen of an organic molecule may be independently replaced by deuterium or a halogen (F, Cl, Br, I).

[0015] In some embodiments of the organic molecule, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted with alkyl substituents; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0016] In some embodiments of the organic molecule, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI is hydrogen, deuterium, halogen, Me, t independently selected from the group consisting of Bu, Ph (=phenyl), cyclohexyl, and carbazole; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0017] In some embodiments of the organic molecule, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from Bu, Ph, cyclohexyl, and carbazole.

[0018] In a preferred embodiment, R II , R IV , R VII and R IX Each of t It's Bu.

[0019] In a preferred embodiment, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of is Me.

[0020] In a preferred embodiment, R XI is H.

[0021] In a preferred embodiment, R XI is Me.

[0022] In a preferred embodiment, R XI is carbazole.

[0023] In certain embodiments, R I , R V , R VI , and / or R X is hydrogen. In a preferred embodiment, R I , R V , R VI , and R X is hydrogen.

[0024] In another embodiment, R XI is hydrogen, methyl, and carbazolyl, Optionally, one or more hydrogen atoms may be R 5 are independently substituted by:

[0025] In a further embodiment of the invention, R XI teeth, hydrogen, Methyl, and carbazolyl.

[0026] In another embodiment, R XI is methyl, and carbazolyl, Optionally, one or more hydrogen atoms may be R 5 are independently substituted by:

[0027] In another embodiment, R XI is halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0028] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia, A and R B forms a monocyclic ring system having 6 C atoms. [ka] Formula Ia In the formula, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0029] In some embodiments, the organic molecule comprises or consists of a structure of formula Ia, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the following is hydrogen, deuterium, halogen, Me, t selected from Bu, Ph, cyclohexyl, and carbazole; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R Xany two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0030] In some embodiments, the organic molecule comprises or consists of a structure of formula Ia, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from Bu, Ph, cyclohexyl, and carbazole.

[0031] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R II , R IV , R VII and R IX Each of t Bu and R XI is H.

[0032] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R II , R IV , R VII and R IX Each of t Bu and R XI is Me.

[0033] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R II , R IV , R VII and R IX Each of t Bu and R XI is carbazole.

[0034] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R II , R IV , R VII and R IX Each of R is Ph (phenyl), III and R VIII Each of the is Me, and R XI is H.

[0035] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the is Me, and R XI is H.

[0036] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of Me and R XI is carbazole.

[0037] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ia, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of is H.

[0038] In one embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, each of which forms a monocyclic ring system having 6 C atoms, RA and R B , and R C and R D This is an embodiment of the present invention. [ka] Formula Ia-2 In the formula, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0039] In certain embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI each independently represents hydrogen, deuterium, a halogen, Me, t independently selected from Bu, Ph, cyclohexyl, and carbazole; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0040] In certain embodiments, the organic molecule comprises or consists of the structure of formula Ia-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from Bu, Ph, cyclohexyl, and carbazole.

[0041] In a further embodiment, R II , R IV , R VII and R IX Each of t Bu and R XI is H.

[0042] In a further embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, R II , R IV , R VII and R IX Each of t Bu and R XI is Me.

[0043] In a further embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, R II , R IV、 R VII and R IX Each of t Bu and R XI is carbazole.

[0044] In a further embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, R II , R IV、 R VII and R IX Each of is Ph and R III and R VIII Each of the is Me, and R XI is H.

[0045] In a further embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, R II , R IV、 R VII and R IX Each of is Ph and R III and R VIII Each of the is Me, and R XI is Me.

[0046] In a further embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the is Me, and R XI is carbazole.

[0047] In a further embodiment, the organic molecule comprises or consists of the structure of formula Ia-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of is H.

[0048] In one embodiment, the organic molecule comprises or consists of a structure of formula Ib, which is represented by R A and R B which form a monocyclic ring system having 5 C atoms, [ka] Formula Ib In the formula, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5- independently substituted by alkyl substituents; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0049] In some embodiments, the organic molecule comprises or consists of a structure of formula Ib, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the following is hydrogen, deuterium, halogen, Me, t independently selected from Bu, Ph, cyclohexyl, and carbazole; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0050] In some embodiments, the organic molecule comprises or consists of a structure of formula Ib, where R I , R II , R III , RIV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from Bu, Ph, cyclohexyl, and carbazole.

[0051] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R II , R IV、 R VII and R IX Each of t Bu and R XI is H.

[0052] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R II , R IV , R VII , and R IX Each of t Bu and R XI is Me.

[0053] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R II , R IV , R VII and R IX Each of t Bu and R XI is carbazole.

[0054] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is H.

[0055] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is Me.

[0056] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is carbazole.

[0057] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of is H.

[0058] In one embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, wherein formula Ib-2 is R A and R B And R C and R D is an example forming a monocyclic ring system with 5 C atoms, [ka] Formula Ib-2 In the formula, R I , RII , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0059] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XIeach independently represents hydrogen, deuterium, a halogen, Me, t selected from Bu, Ph, cyclohexyl, carbazole; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0060] In some embodiments, the organic molecule comprises or consists of the structure of formula Ib-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI each independently represents hydrogen, deuterium, a halogen, Me, t It is selected from Bu, Ph, cyclohexyl, and carbazole.

[0061] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R II , R IV , R VII and R IX Each of t Bu and R XI is H.

[0062] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R II , R IV , R VII and R IX Each of t Bu and R XI is Me.

[0063] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R II , R IV , R VII and R IX Each of t Bu and R XI is carbazole.

[0064] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is H.

[0065] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is Me.

[0066] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is carbazole.

[0067] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ib-2, R I , R II , R III , R IV , R V , RVI , R VII , R VIII , R IX , R X and R XI Each of is H.

[0068] In one embodiment, the organic molecule comprises or consists of a structure of formula Ic, where Ic is A and R B is an example forming a monocyclic ring system having 6 C atoms, where some of the hydrogens are replaced by methyl groups, [ka] Formula Ic In the formula, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; Optionally, R I , R II , R III , R IV , R V , RVI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0069] In some embodiments, the organic molecule comprises or consists of a structure of formula Ic, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of the following is hydrogen, deuterium, halogen, Me, t independently selected from Bu, Ph, cyclohexyl, and carbazole; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0070] In some embodiments, the organic molecule comprises or consists of a structure of formula Ic, where R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and RD Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from Bu, Ph, cyclohexyl, and carbazole.

[0071] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R II , R IV , R VII and R IX Each of t Bu and R XI is H.

[0072] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R II , R IV , R VII and R IX Each of t Bu and R XI is Me.

[0073] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R II , R IV , R VII and R IX Each of t Bu and R XI is carbazole.

[0074] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is H.

[0075] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R II , R IV , R VII and R IX Each of is Ph and RIII and R VIII Each of the groups is Me, and each of the groups is R XI is Me.

[0076] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is carbazole.

[0077] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R C and R D Each of is H.

[0078] In one embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, A and R B And R C and R D is an example of a monocyclic ring system having 6 C atoms, some of the hydrogen atoms of which are replaced by methyl groups, [ka] Formula Ic-2 In the formula, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX, R X and R XI Each of the elements is selected from hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; Optionally, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen may be independently replaced by Me.

[0079] In some embodiments, the organic molecule comprises or consists of the structure of formula Ic-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t independently selected from Bu, Ph, cyclohexyl, and carbazole; Optionally, R I , R II , R III , RIV , R V , R VI , R VII , R VIII , R IX and R X any two adjacent ones of the above together form a monocyclic ring system having 5 to 8 C atoms, Optionally, each hydrogen can be replaced independently by Me.

[0080] In some embodiments, the organic molecule comprises or consists of the structure of formula Ic-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t are independently selected from Bu, Ph, cyclohexyl, and carbazole.

[0081] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R II、 R IV , R VII , and R IX Each of t Bu and R XI is H.

[0082] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R II、 R IV , R VII , and R IX Each of t Bu and R XI is Me.

[0083] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R II、 R IV , R VII , and RIX Each of t Bu and R XI is carbazole.

[0084] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is H.

[0085] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is Me.

[0086] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R II , R IV , R VII and R IX Each of is Ph and R III and R VIII Each of the groups is Me, and each of the groups is R XI is carbazole.

[0087] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-2, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X and R XI Each of is H.

[0088] In one embodiment, the organic molecule comprises or consists of the structure of formula Ic-3, A and R B , R C and R D , R II and R III And R VIII and R IX is an example forming a monocyclic ring system having 6 C atoms, some of the hydrogens of which are replaced by methyl groups, [ka] Formula Ic-3 In the formula, R I , R IV , R V , R VI , R VII , R X and R XI are hydrogen, deuterium, halogen, C 1 ~C 12 -alkyl, C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted by alkyl substituents; C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms are C 1 ~C 5 - independently substituted with alkyl substituents.

[0089] In some embodiments, the organic molecule comprises or consists of a structure of formula Ic-3, R I , R IV , R V , R VI , R VII , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me,t Independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0090] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-3, R XI is H.

[0091] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-3, R XI is Me.

[0092] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ic-3, R XI is carbazole.

[0093] In one embodiment, the organic molecule comprises or consists of the structure of formula Id: [ka] Expression Id

[0094] In some embodiments, the organic molecule comprises or consists of a structure of formula Id, II , R IV , R III , R VIII , R VII , R IX and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0095] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Id, XI is H.

[0096] In another embodiment, the organic molecule comprises or consists of a structure of formula Id, XI is halogen, C 1 ~C12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0097] In another embodiment, the organic molecule comprises or consists of a structure of formula Id, XI is halogen, Methyl, and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0098] In another embodiment, the organic molecule comprises or consists of a structure of formula ID, XI teeth, Methyl, and carbazolyl.

[0099] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Id, XI is Me.

[0100] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Id, XI is carbazole.

[0101] In one embodiment, the organic molecule comprises or consists of a structure of formula Ie: [ka] Formula Ie

[0102] wherein in some embodiments, the organic molecule comprises or consists of a structure of formula Ie, R II , R III , R VIII , R IX and R XI Each of the following is hydrogen, deuterium, halogen, Me, t are independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0103] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Ie, R XI is H.

[0104] In another embodiment, the organic molecule comprises or consists of a structure of formula Ie, where R XI is halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0105] In another embodiment, the organic molecule comprises or consists of a structure of formula Ie, R XI teeth, halogen, Methyl, and C 3 ~C 15Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0106] In another embodiment, the organic molecule comprises or consists of a structure of formula Ie, R XI is selected from the group consisting of hydrogen, methyl, and carbazolyl.

[0107] In another embodiment, the organic molecule comprises or consists of a structure of formula Ie, R XI is selected from the group consisting of methyl and carbazolyl.

[0108] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Ie, R XI is Me.

[0109] In a preferred embodiment, the organic molecule comprises or consists of a structure of formula Ie, R XI is carbazole.

[0110] In one embodiment, the organic molecule comprises or consists of a structure of formula Le-0. [ka] Formula Ie-0

[0111] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-0, where R XI is hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0112] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-0, R I , R IV , R V , R VI , R VII , RX and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0113] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-0, R I , R IV , R V , R VI , R VII , and R X is hydrogen.

[0114] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-0, R XI is H.

[0115] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-0, R XI teeth, halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0116] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-0, R XI is halogen, methyl, and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0117] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-0, R XI is selected from the group consisting of methyl and carbazolyl.

[0118] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-0, R XI is Me.

[0119] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-0, R XI is carbazole.

[0120] In one embodiment, the organic molecule comprises or consists of the structure of formula Ie-1: [ka] Formula Ie-1

[0121] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-1, where R XI is hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0122] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-1, R XI is H.

[0123] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-1, XI is halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0124] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-1, R XI is halogen, methyl, and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0125] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-1, R XI is selected from the group consisting of methyl and carbazolyl.

[0126] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-1, R XI is Me.

[0127] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-1, R XI is carbazole.

[0128] In one embodiment, the organic molecule comprises or consists of the structure of formula Ie-2: [ka] Formula Ie-2

[0129] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-2, wherein R XI is hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0130] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-2, I , R IV , R V , R VI , R VII , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0131] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-2, I , R IV , R V , R VI , R VII , and R X is hydrogen.

[0132] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-2, R XI is H.

[0133] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-2, R XI is halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0134] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-2, XI is halogen, methyl, and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0135] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-2, XI is selected from the group consisting of methyl and carbazolyl.

[0136] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-2, R XI is Me.

[0137] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-2, R XI is carbazole.

[0138] In one embodiment, the organic molecule comprises or consists of the structure of formula Ie-3: [ka] Formula Ie-3

[0139] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-3, wherein R XI is hydrogen, deuterium, halogen, Me, tIt is selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0140] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-3, R I , R IV , R V , R VI , R VII , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0141] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-3, R I , R IV , R V , R VI , R VII , and R X is hydrogen.

[0142] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-3, R XI is H.

[0143] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-3, R XI is halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5and independently substituted by:

[0144] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-3, R XI is halogen, methyl, and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0145] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-3, R XI is selected from the group consisting of methyl and carbazolyl.

[0146] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-3, R XI is Me.

[0147] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-3, R XI is carbazole.

[0148] In one embodiment, the organic molecule comprises or consists of the structure of formula Ie-4: [ka] Formula Ie-4

[0149] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-4, wherein R XI is hydrogen, deuterium, halogen, Me, t It is selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0150] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-4, R I , RIV , R V , R VI , R VII , R X and R XI Each of the following is hydrogen, deuterium, halogen, Me, t Independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole.

[0151] In some embodiments, the organic molecule comprises or consists of a structure of formula Ie-4, R I , R IV , R V , R VI , R VII , and R X is hydrogen.

[0152] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-4, R XI is H.

[0153] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-4, R XI is halogen, C 1 ~C 12 -alkyl, Optionally, one or more hydrogen atoms may be R 5 independently substituted by C 6 ~C 18 -aryl, Optionally, one or more hydrogen atoms may be R 5 and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0154] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-4, R XI is halogen, methyl, and C 3 ~C 15 Heteroaryl, Optionally, one or more hydrogen atoms may be R 5 and independently substituted by:

[0155] In another embodiment, the organic molecule comprises or consists of the structure of formula Ie-4, R XI is selected from the group consisting of methyl and carbazolyl.

[0156] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-4, R XI is Me.

[0157] In a preferred embodiment, the organic molecule comprises or consists of the structure of formula Ie-4, R XI is carbazole.

[0158] In one embodiment, the organic molecule comprises or consists of a structure of formula If: [ka] Expression If

[0159] As used throughout this application, the terms "aryl" and "aromatic" may be understood in the broadest sense as any monocyclic, bicyclic or polycyclic aromatic moiety. Thus, an aryl group contains 6 to 60 aromatic ring atoms, and a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout this application, the number of aromatic ring atoms may be given as a subscript in the definition of a particular substituent. In particular, a heteroaromatic ring contains 1 to 3 heteroatoms. The terms "heteroaryl group" and "heteroaromatic" may also be understood in the broadest sense as any monocyclic, bicyclic or polycyclic heteroaromatic moiety containing at least one heteroatom. Each heteroatom may be the same or different and may be individually selected from the group consisting of N, O and S. Thus, the term "arylene" denotes a divalent substituent that bears two attachment sites with other molecular structures, thereby functioning as a linker structure. In the event that a group in an exemplary embodiment is defined differently from the definitions given herein, for example, the number of aromatic ring atoms or the number of heteroatoms differs from the definitions given, the definitions in the exemplary embodiment shall apply. In accordance with the present invention, a fused (cyclized) aromatic or heteroaromatic polycyclic ring is constructed of two or more single aromatic or heteroaromatic rings that undergo a condensation reaction to form a polycyclic ring.

[0160] In particular, as used throughout, the terms "aryl group" and "heteroaryl group" refer to any of the following: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthridine, phenanthridine, pyridoimidazole, pyridine ... and benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or a combination of the aforementioned groups.

[0161] As used throughout, the term "cyclic group" can be understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0162] As used throughout, the term "biphenyl" as a substituent can be understood in its broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined with respect to the point of attachment to another chemical moiety.

[0163] As used throughout, the term "alkyl group" can be understood in its broadest sense as any straight-chain, branched, or cyclic alkyl substituent. In particular, the term alkyl includes methyl (Me), ethyl (Et), n-propyl (N-propyl ... ethyl (Et), ethyl 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, 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-trifluorethyl, 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-dec-1-yl -yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexadec-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-hexadec-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.

[0164] As used throughout, the term "alkenyl" includes straight-chain, branched, and cyclic alkenyl substituents. The term "alkenyl group" includes substituents that are, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0165] As used throughout, the term "alkynyl" includes straight-chain, branched, and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, or octynyl.

[0166] As used throughout, the term "alkoxy" includes straight chain, branched, and cyclic alkoxy substituents. The term "alkoxy group" illustratively includes methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, and 2-methylbutoxy.

[0167] As used throughout, the term "thioalkoxy" includes straight chain, branched and cyclic thioalkoxy substituents, where the O of the exemplary alkoxy group is replaced with S.

[0168] As used throughout, the terms "halogen" and "halo" may be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0169] Whenever hydrogen (H) is mentioned in this specification, it can also be replaced with deuterium.

[0170] It is understood that when a fragment of a molecule is described as being a substituent or otherwise attached to another moiety, the name may be written as if it were the fragment (e.g., naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of naming the substituent or attached fragment are considered equivalent.

[0171] In one embodiment, the organic molecules according to the invention have an excited state lifetime of 150 μs or less, 100 μs or less, in particular 50 μs or less, more preferably 10 μs or less, or 7 μs or less at room temperature in a film of poly(methyl methacrylate) (PMMA) having 5 wt. % of the organic molecules.

[0172] In one embodiment, the organic molecules according to the invention have an excited state lifetime of 150 μs or less, 100 μs or less, in particular 50 μs or less, preferably 10 μs or less, or 7 μs or less at room temperature in a film of poly(methyl methacrylate) (PMMA) having 1-5 wt. %, in particular 2 wt. %, of the organic molecules according to the invention.

[0173] In a further embodiment of the present invention, the organic molecule according to the present invention has an emission peak in the visible or near ultraviolet region, i.e. in the wavelength region of 380 nm to 800 nm, with a full width at half maximum of less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV, or even less than 0.17 eV at room temperature in the state of a poly(methyl methacrylate) (PMMA) film containing 5 wt % of the organic molecule.

[0174] In a further embodiment of the present invention, the organic molecule according to the present invention has an emission peak in the visible or near ultraviolet region, i.e. in the wavelength region of 380 nm to 800 nm, with a full width at half maximum of less than 0.23 eV, in particular less than 0.20 eV, preferably less than 0.19 eV, even more preferably less than 0.18 eV or even less than 0.17 eV at room temperature in the state of a poly(PMMA) film containing 1 to 5 wt. %, in particular 2 wt. %, of the organic molecule.

[0175] The energies of orbital states and excited states can be determined by any experimental method. HOMO The energy of the lowest unoccupied molecular orbital E is determined to an accuracy of 0.1 eV by cyclic voltammetry measurements using methods known to those skilled in the art. LUMO The energy of E HOMO +E gap(In the formula, E gap is calculated as follows: Unless otherwise stated, for host compounds, E is taken as the onset of the emission spectrum for a film with 10 wt % host in poly(methyl methacrylate) (PMMA). gap For the emitter molecules, E is used as the energy in the excitation and emission spectra of a film with 10 wt. % emitter in crosslinked PMMA. gap For the organic molecules according to the invention, the energies in the excitation and emission spectra of a film with 5% by weight of the emitter in crosslinked PMMA are calculated as E gap Request.

[0176] The energies of orbital states and excited states can be determined by any experimental method. HOMO The energy of the lowest unoccupied molecular orbital E is determined to an accuracy of 0.1 eV by cyclic voltammetry measurements using methods known to those skilled in the art. LUMO The energy of E HOMO +E gap (In the formula, E gap Unless otherwise stated, for host compounds, E is taken as the onset of the emission spectrum for a film with 10 wt % host in poly(methyl methacrylate) (PMMA). gap For the emitter molecules, E is used as the energy in the excitation and emission spectra of a film with 10 wt. % emitter in crosslinked PMMA. gap For the organic molecules according to the invention, the energies in the excitation and emission spectra of a film having 1 to 5% by weight, in particular 2% by weight, of the emitter in the crosslinked PMMA are given as E gap Request.

[0177] The energy of the first excited triplet state T1 is determined from the onset of the emission spectrum at low temperature, usually 77 K. For host compounds in which the first excited singlet state and the lowest triplet state are separated in energy by >0.4 eV, phosphorescence is usually visible in the steady-state spectrum in 2-Me-THF. The triplet energy can be 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 film of PMMA with 10 wt. % emitter unless otherwise stated, and in the case of organic molecules according to the invention, measured in a film of PMMA with 1 wt. % of organic molecules according to the invention. For both the host compounds and the emitter compounds, the energy of the first excited singlet state S1 is determined from the onset of the emission spectrum measured in a film of PMMA with 10 wt. % of the host compound or emitter compound, unless otherwise stated, and in the case of the organic molecules of the invention, measured in a film of PMMA with 1 wt. % of the organic molecules of the invention.

[0178] The onset of the emission spectrum is determined by calculating the intersection of the x-axis with a tangent to the emission spectrum, which is set at the high energy side of the emission band and at half maximum intensity of the emission spectrum.

[0179] In one embodiment, the organic molecules according to the invention have an emission spectrum onset that is energetically close to the emission maximum, i.e. the energy difference between the emission spectrum onset and the energy of the emission maximum is less than 0.14 eV, preferably less than 0.13 eV, or even less than 0.12 eV, while in a film of poly(methyl methacrylate) (PMMA) with 5% by weight of the organic molecules at room temperature, the full width at half maximum (FWHM) of the organic molecules is less than 0.23 eV, preferably less than 0.20 eV, more preferably less than 0.19 eV, even more preferably less than 0.18 eV, or even less than 0.17 eV, resulting in a CIE y coordinate of less than 0.20, preferably less than 0.18, more preferably less than 0.16, or even more preferably less than 0.14.

[0180] In one embodiment, the organic molecules according to the invention have an emission spectrum onset which is energetically close to the emission maximum, i.e. the energy difference between the emission spectrum onset and the energy of the emission maximum is less than 0.14 eV, in particular less than 0.13 eV, or even less than 0.12 eV, while in a film of poly(methyl methacrylate) (PMMA) with 1-5% by weight, in particular 2% by weight, of the organic molecules at room temperature, the full width at half maximum (FWHM) of the organic molecules is less than 0.23 eV, in particular less than 0.20 eV, preferably less than 0.19 eV, more preferably less than 0.18 eV, or even less than 0.17 eV, resulting in a CIE y coordinate of less than 0.20, in particular less than 0.18, preferably less than 0.16, or even more preferably less than 0.14.

[0181] A further aspect of the present invention relates to the use of an organic molecule according to the invention as an emitter or as an absorber and / or as a host material and / or as an electron transport material and / or as a hole injection material and / or as a hole blocking material in an optoelectronic device.

[0182] A preferred embodiment relates to the use of organic molecules according to the invention as emitters in optoelectronic devices.

[0183] An optoelectronic device may be broadly understood as any device based on organic materials suitable for emitting light in the visible or near ultraviolet (UV) range, i.e. in the wavelength range of 380-800 nm. More preferably, an optoelectronic device may be capable of emitting light in the visible range, i.e. in the range of 400 nm to 800 nm.

[0184] In the context of such use, the optoelectronic device is more particularly selected from the group consisting of: Organic Light Emitting Diodes (OLEDs), Light-emitting electrochemical cells, OLED sensors, in particular in gas and vapour sensors that are not hermetically sealed against the environment; Organic diodes, · Organic solar cells, Organic transistors, Organic field-effect transistors, Organic lasers, and Down-conversion element.

[0185] In preferred embodiments within the context of such a use, 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.

[0186] When used, the fraction of the organic molecules according to the invention in the light-emitting layer in an optoelectronic device, more particularly in an OLED, is 0.1-99% by weight, more particularly 1%-80% by weight. In an alternative embodiment, the proportion of the organic molecules in the light-emitting layer is 100% by weight.

[0187] In one embodiment, the light-emitting layer comprises not only an organic molecule according to the present invention but also a host material whose triplet (T1) and singlet (S1) energy levels are energetically higher than the triplet (T1) and singlet (S1) energy levels of the organic molecule.

[0188] A further aspect of the invention relates to a composition comprising or consisting of: (a) at least one organic molecule according to the invention, in particular in the form of an emitter and / or host, and (b) one or more emitter and / or host materials different from the organic molecules according to the invention; and (c) optionally one or more dyes and / or one or more solvents.

[0189] In one embodiment, the light-emitting layer comprises (or consists essentially of) a composition comprising or consisting of: (a) at least one organic molecule according to the invention, in particular in the form of an emitter and / or host, and (b) one or more emitter and / or host materials different from the organic molecules according to the invention; and (c) optionally one or more dyes and / or one or more solvents.

[0190] In certain embodiments, the emissive layer EML comprises (or consists essentially of) a composition comprising or consisting of: (i) 0.1 to 10% by weight, preferably 0.5 to 5% by weight, in particular 1 to 3% by weight, of one or more organic molecules according to the invention, (ii) 5 to 99% by weight, preferably 15 to 85% by weight, in particular 20 to 75% by weight, of at least one host compound H, and (iii) 0.9 to 94.9% by weight, preferably 14.5 to 80% by weight, in particular 24 to 77% by weight, of at least one further host compound D, which has a structure different from that of the molecule according to the invention, and (iv) optionally 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of a solvent, and (v) optionally 0-30% by weight, in particular 0-20% by weight, preferably 0-5% by weight, of at least one further emitter molecule F having a structure different from that of the molecule according to the invention.

[0191] Preferably, energy can be transferred from the host compound H to one or more organic molecules 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 according to the present invention E and / or from the first excited singlet state S1(H) of the host compound H to the first excited singlet state S1(E) of one or more organic molecules according to the present invention E.

[0192] In one embodiment, the host compound H has an energy E in the range of −5 to −6.5 eV. HOMO (H) has a highest occupied molecular orbital HOMO(H), and at least one further host compound D has an energy E HOMO (D)(E HOMO (H)>E HOMO It has the highest occupied molecular orbital HOMO (D).

[0193] In a further embodiment, the host compound H has an energy E LUMO (H) has a lowest occupied molecular orbital LUMO(H), and at least one further host compound D has energy E LUMO (D)(E LUMO (H)>E LUMO It has the lowest occupied molecular orbital LUMO (D), which is (D).

[0194] In one embodiment, the host compound H has an energy E HOMO The highest occupied molecular orbital HOMO(H) with (H) and energy E LUMO (H) having the lowest occupied molecular orbital LUMO (H), At least one further host compound D has an energy E HOMOThe highest occupied molecular orbital HOMO(D) with (D) and energy E LUMO (D) has a lowest occupied molecular orbital LUMO (D), The organic molecule according to the present invention E has energy E HOMO (E) Highest occupied molecular orbital HOMO(E) and energy E LUMO (E) having a lowest occupied molecular orbital LUMO (E); During the ceremony, E HOMO (H)>E HOMO (D) and the energy level of the highest occupied molecular orbital HOMO (E) of the organic molecule of the present invention E (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 -0.1 eV to 0.1 eV; E LUMO (H)>E LUMO (D) and the energy level of the lowest occupied molecular orbital LUMO (E) of the organic molecule according to the present invention (E LUMO (E)) and the lowest occupied molecular orbital LUMO (D) of at least one further 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.

[0195] In one embodiment according to the present invention, the host compound D and / or the host compound H is a thermally-activated delayed fluorescence (TADF) material. TADF materials have an energy difference of 2500 cm, which corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1). -1 Less than ΔE ST Preferably, the TADF material has a 3000 cm -1 less than 1500 cm -1less than 1000 cm -1 Less than or even 500cm -1 Less than ΔE ST It presents value.

[0196] In one embodiment, the host compound D is a TADF material and the host compound H is a 2500 cm -1 ΔE exceeds ST In certain embodiments, the host compound D is a TADF material and the host compound H is selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0197] In one embodiment, the host compound H is a TADF material and the host compound D is a 2500 cm -1 ΔE exceeds ST In certain embodiments, the host compound H is a TADF material and the host compound D is selected from the group consisting of T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), and / or TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine).

[0198] In a further aspect, the present invention relates to an optoelectronic device comprising an organic molecule or composition as described herein, more particularly in the form of a device selected from the group consisting of organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, more particularly gas and vapor sensors that are not hermetically sealed from the outside, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and down conversion elements.

[0199] 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.

[0200] In one embodiment of the optoelectronic device of the present invention, an organic molecule according to Invention E is used as emissive material in the emissive layer EML.

[0201] In one embodiment of the optoelectronic device of the present invention, the light-emitting layer EML consists of the inventive composition described herein.

[0202] When the optoelectronic device is an OLED, it has, for example, the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer, HIL 4. Hole transport layer, HTL 5. Electron Blocking Layer, EBL 6. Emitting layer, EML 7. Hole Blocking Layer, HBL 8.Electron transport layer, ETL 9.Electron injection layer, EIL 10. Cathode layer In this case, the OLED comprises layers selected from the group of HIL, HTL, EBL, HBL, ETL and EIL, only optionally the different layers may be fused together and the OLED may comprise two or more of each layer type defined above.

[0203] The optoelectronic device may also, in one embodiment, include one or more protective layers that protect the device from damaging exposure to harmful species in the environment, including moisture, vapors and / or gases.

[0204] In one embodiment according to the invention, the optoelectronic device is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer 3.Electron injection layer, EIL 4.Electron transport layer, ETL 5. Hole Blocking Layer, HBL 6. Light-emitting layer, B 7. Electron Blocking Layer, EBL 8. Hole transport layer, HTL 9. Hole injection layer, HIL 10. Anode layer A In this case, the OLED comprises layers selected from the group of HIL, HTL, EBL, HBL, ETL and EIL, only optionally the different layers may be fused together and the OLED may comprise two or more of each layer type defined above.

[0205] In one embodiment of the present invention, the optoelectronic device is an OLED that may have a stacked structure. In this structure, individual building blocks are stacked on top of each other, unlike the typical structure in which OLEDs are arranged side by side. OLEDs exhibiting a stacked structure can be used to produce blended light, in particular white light can be produced by stacking blue, green and red OLEDs. Furthermore, OLEDs exhibiting a stacked structure may include a charge generation layer (CGL), which is usually located between two OLED subunits and usually consists of an n-doped and a p-doped layer, with the n-doped layer of one CGL usually located closer to the anode layer.

[0206] In one embodiment of the present invention, the optoelectronic device is an OLED, which comprises two or more light-emitting layers between an anode and a cathode. In particular, this so-called serial OLED comprises three light-emitting layers, one light-emitting layer emitting red light, one light-emitting layer emitting green light, and one light-emitting layer emitting blue light, and may optionally comprise additional layers between each of the light-emitting layers, such as charge-generating layers, blocking layers, or transport layers. In a further embodiment, the light-emitting layers are stacked adjacently. In a further embodiment, the serial OLED comprises a charge-generating layer between each two of the light-emitting layers. Furthermore, the light-emitting layers separated by adjacent light-emitting layers or charge-generating layers may be fused together.

[0207] The substrate may be formed by any material or composition of materials. Most often used as substrate is a glass slide. Alternatively, a thin metal layer (e.g. copper, gold, silver or aluminum film) or a plastic film or slide may be used. This allows a higher degree of flexibility. The anode layer A is mainly composed of a material that makes it possible to obtain an (essentially) transparent film. Either the anode layer A or the cathode layer C is transparent, since at least one of both electrodes should be (essentially) transparent to allow light emission from the OLED. Preferably, the anode layer A contains in large part or consists of transparent conductive oxides (TCOs). Such an anode layer 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.

[0208] The anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO 3 ) 0.9 (SnO 2 ) 0.1). The roughness of the anode layer A caused by the transparent conductive oxide (TCO) can be compensated for by using a hole injection layer (HIL). Furthermore, the HIL can facilitate the injection of pseudo charge carriers (i.e. holes) in the sense that the transport of pseudo charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) can be made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonate (PSS), MoO 2 , V 2 O 5 , CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also block the diffusion of metals from the anode layer A into the hole transport layer (HTL). The HIL can be selected from a wide variety of materials, including PEDOT:PSS (poly-3,4-ethylenedioxythiophene:polystyrenesulfonate), PEDOT (poly-3,4-ethylenedioxythiophene), mMTDATA (4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N'-nis-(1- naphthalenyl-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-di-[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine), for example.

[0209] Adjacent to the anode layer A or the hole injection layer (HIL) is usually a hole transport layer (HTL). Any hole transport compound can be used herein. For example, electron rich heteroaromatic compounds, such as triarylamines and / or carbazoles, can be used as hole transport compounds. The HTL can reduce the energy barrier between the anode layer A and the emissive layer EML. The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a high energy level comparable to their triplet state T1. For example, the hole transport layer (HTL) may be a star-shaped heterocycle, such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4'-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzeneamine]), 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, , NPNPB, MeO-TPD, HAT-CN and / or TrisPcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Furthermore, the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix. Transition metal oxides, such as vanadium oxide, molybdenum oxide or tungsten oxide, can be used, for example, as inorganic dopants. Tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes can for example be used as organic dopants.

[0210] The EBL may include, for example, mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N'-dicarbazolyl-1,4-dimethylbenzene).

[0211] The emissive layer EML is typically disposed adjacent to a hole-transporting layer (HTL). The emissive layer EML comprises at least one emissive molecule. In particular, the EML comprises at least one emissive molecule according to invention E. In one embodiment, the emissive layer comprises only organic molecules according to the invention. Typically, the EML additionally comprises one or more host materials H. For example, the host material H can be CBP (4,4'-bis-(N-carbazolyl)-biphenyl), mCP, mCBP, etc. Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]etheroxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazo The host material H is generally selected from 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine). The host material H should generally be selected to exhibit a first triplet energy level (T1) and a first singlet energy level (S1) that are energetically higher than the first triplet energy level (T1) and the first singlet energy level (S1) of the organic molecule.

[0212] In one embodiment according to the invention, the EML comprises a so-called mixed host system having at least one hole-dominant host and one electron-dominant host. In a particular embodiment, the EML comprises exactly one light-emitting organic molecule according to the invention and a mixed host system comprising T2T as an electron-dominant host and 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 as a hole-dominant host. In a further embodiment, the EML comprises 50-80% by weight, preferably 60-75% 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; 10-45% by weight, preferably 15-30% by weight, of T2T, and 5-40% by weight, preferably 10-30% by weight, of an emissive molecule according to the invention.

[0213] Adjacent to the light-emitting layer EML, an electron transport layer (ETL) may be located. Any electron transporter may be used herein. Illustratively, electron-deficient compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxides, and sulfones 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 be NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq 3 (aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-di(2,2'-bipyridin-5-yl)triphenyl), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and / or BTB (4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Optionally, the ETL may be doped with a material such as Liq. The electron transport layer (ETL) may also block holes or a hole blocking layer (HBL) is introduced.

[0214] HBL is, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq 3(aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzol / 1,3,5-tris(carbazol-9-yl)benzene).

[0215] 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 may also consist (essentially) of an opaque metal, such as Mg, Ca, or Al. Alternatively or additionally, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also consist of nanoscale silver conductors.

[0216] The OLED may further optionally include a protective layer between the electron transport layer (ETL) and the cathode layer C (which may also be named the electron injection layer (EIL)). This layer may be made of any of a variety of materials, including lithium fluoride, cesium fluoride, silver, Liq (8-hydroxyquinolinolatolithium), Li 2 O, BaF 2 , MgO and / or NaF.

[0217] Optionally, the electron transporting layer (ETL) and / or the hole blocking layer (HBL) may further comprise one or more host compounds H.

[0218] To further modify the emission and / or absorption spectrum of the emissive layer EML, the emissive layer EML may further comprise one or more additional emitter molecules F. Such emitter molecules F may be any emitter molecule known in the art. Such emitter molecules F are preferably molecules with a structure different from that of the molecules according to the invention E. The emitter molecules F may optionally be TADF emitters. Alternatively, the emitter molecules F may optionally be fluorescent and / or phosphorescent emitter molecules that can shift the emission and / or absorption spectrum of the emissive layer EML. By way of example, triplet and / or singlet excitons are transferred from the organic emitter molecules according to the invention to the emitter molecules F and then relax to the ground state S0 by emitting light that is usually red-shifted compared to the emission 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).

[0219] Optionally, the optoelectronic device (e.g., OLED) may be, for example, an essentially white optoelectronic device. For example, such a white optoelectronic device may include at least one (deep) blue emitter molecule and one or more emitter molecules that emit green light and / or red light. Optionally, then, there may also be energy transmission between two or more of the above-mentioned molecules.

[0220] As used herein, unless more specifically defined in a particular context, the nomenclature of the colors of light emitted and / or absorbed is as follows: Purple: Wavelength range >380~420nm Deep blue: Wavelength range >420~480nm Light blue: Wavelength range >480~500nm Green: Wavelength range >500~560nm Yellow: Wavelength range >560~580nm Orange: Wavelength range >580~620nm Red: Wavelength range >620~800nm

[0221] For the emitter molecules, these colors indicate emission maxima. Thus, for example, deep blue emitters have emission maxima in the range >420-480 nm, light blue emitters have emission maxima in the range >480-500 nm, green emitters have emission maxima in the range >500-560 nm, and red emitters have emission maxima in the range >620-800 nm.

[0222] Deep blue emitters may preferably have an emission maximum less than 480 nm, more preferably less than 470 nm, even more preferably less than 465 nm or even less than 460 nm. The emission maximum is usually greater than 420 nm, preferably greater than 430 nm, more preferably greater than 440 nm or even greater than 450 nm.

[0223] Thus, a further aspect of the invention is a 2 and / or an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm, and / or a maximum emission of 500 cd / m 2 A further aspect of the invention relates to an OLED whose emission exhibits a CIEy color coordinate of less than 0.45, preferably less than 0.30, more preferably less than 0.20 or even more preferably less than 0.15 or even less than 0.10.

[0224] A further aspect of the present invention relates to an OLED that emits light at a distinct color point.According to the present invention, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)).In one aspect, the OLED according to the present invention emits light with the FWHM of the main emission peak being less than 0.30 eV, preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.19 eV, or even less than 0.17 eV.

[0225] A further aspect of the invention relates to OLEDs that emit with CIEx and CIEy color coordinates that are close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of the primary blue color (CIEx=0.131 and CIEy=0.046) as defined in ITU-R Recommendation BT.2020 (Rec.2020), and are therefore suitable for use in ultra-high definition (UHD) displays, such as UHD-TVs. Thus, a further aspect of the present invention relates to an OLED whose emission exhibits CIEx colour coordinates between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20, or even more preferably between 0.08 and 0.18, or even between 0.10 and 0.15, and / or CIEy colour coordinates between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20, or even more preferably between 0.03 and 0.15, or even between 0.04 and 0.10.

[0226] In a further aspect, the present invention relates to a method for producing an optoelectronic component, in which the organic molecules of the present invention are used.

[0227] The optoelectronic devices, particularly the OLEDs according to the present invention, can be fabricated by any means of deposition and / or liquid processing. Thus, at least one layer can be - Prepared by sublimation process, - Prepared by organic vapor phase deposition process; - Prepared by carrier gas sublimation process, - Solution processed or solution printed.

[0228] The methods used to manufacture optoelectronic devices, in particular OLEDs according to the present invention, are known in the art. The different layers are individually and sequentially deposited on a suitable substrate by subsequent vapor deposition processes. The individual layers can be deposited using the same or different deposition methods.

[0229] Vapor deposition processes include, for example, thermal (co)evaporation, chemical vapor deposition and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. The individual layers may be processed from solutions or dispersions with sufficient solvent. Solution deposition processes illustratively include, for example, spin coating, dip coating and jet printing. Liquid processing may optionally be performed under an inert atmosphere (e.g., under a nitrogen atmosphere) and the solvent may be completely or partially removed by means known in the state of the art. EXAMPLES

[0230] General synthetic scheme I General synthetic scheme I provides a synthetic scheme for organic molecules according to the invention, I =R X , R II =R IX , R III =R VIII , R IV =R VII and R V =R VI , R A =R D and R B =R C . [ka] [ka] [ka] [ka]

[0231] The general procedure for synthetic AAV1 is as follows. [ka]

[0232] E1 (1.00 equivalent), E2 (2.20 equivalent), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine P( t Bu) 3 (0.04 equivalents, CAS: 13716-12-6), and sodium tert-butoxide NaO t Bu (5.00 equiv., CAS: 865-48-5) is stirred in toluene at 90 °C under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic layers are washed with MgSO 4 The crude product is dried over hexane and then the solvent is removed under reduced pressure to give I1 as a solid.

[0233] The general procedure for synthetic AAV2 is as follows. [ka]

[0234] I1 (1.00 equivalent), E3 (2.20 equivalent), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine P( t Bu) 3(0.04 equivalents, CAS: 13716-12-6), and sodium tert-butoxide NaO t Bu (5.00 equiv., CAS: 865-48-5) is stirred in toluene at 110 °C under nitrogen atmosphere. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the phases are separated. The combined organic layers are washed with MgSO 4 The crude product is dried over hexane and then the solvent is removed under reduced pressure. The crude product is purified by recrystallization or column chromatography to give I2 as a solid.

[0235] The general procedure for synthetic AAV2-a is as follows. [ka]

[0236] I2-a (1 equiv.), E2a (8 equiv.), palladium(II) acetate (CAS: 3375-31-3, 0.06 equiv.), X-Phos (CAS: 564483-18-7, 0.12 equiv.), and tripotassium phosphate (12 equiv.) were stirred in dioxane / toluene 1:1 under nitrogen atmosphere at 100 °C for 20 h. After cooling to room temperature (rt), the reaction mixture was extracted with DCM and brine and the phases were separated. The combined organic layer was washed with MgSO 4 The crude product is dried over hexane and then the solvent is removed under reduced pressure. The crude product is purified by recrystallization or column chromatography to give I2 as a solid.

[0237] The general procedure for synthetic AAV3 is as follows. [ka]

[0238] I2 (1.00 equiv.) is stirred in tetrahydrofuran under nitrogen at -5°C. tBuLi, 2.20 equiv., CAS 594-19-4) is added dropwise and the reaction is stirred at 0 °C. Lithiation is quenched by slow addition of trimethylborate (6.00 equiv., CAS 121-43-7) at room temperature. The reaction mixture is heated to 40 °C overnight, after which the reaction mixture is cooled to room temperature. Water is added and the mixture is stirred for an additional 2 h. After extraction with ethyl acetate, the organic phase is washed with MgSO 4 The mixture is dried at rt and the solvent is removed under reduced pressure, and the resulting crude product is purified by recrystallization and column chromatography to give I3 as a solid.

[0239] The general procedure for synthetic AAV4 is as follows. [ka]

[0240] I3 (1.00 equiv.) is stirred in chlorobenzene under a nitrogen atmosphere. N,N-diisopropylethylamine (10.0 equiv., CAS 7087-68-5) and aluminum chloride (AlCl 3 , 10.0 equiv., CAS 7446-70-0) is added and the reaction mixture is heated to 120° C. After 60 minutes, N,N-diisopropylethylamine (5.00 equiv., CAS 7087-68-5) and aluminum chloride (AlCl 3 , 5.00 equiv., CAS7446-70-0) is added and the reaction mixture is stirred for 1.5 h. After cooling to room temperature, the reaction mixture is washed on ice and extracted with DCM and water. The organic phase is washed with MgSO 4 The mixture is dried over hexane and the solvent is partially removed under reduced pressure. The crude product P1 is purified by recrystallization or column chromatography.

[0241] General synthetic scheme II General synthetic scheme I provides a synthetic scheme for an organic molecule, A =R D , R B =R C , R I =R X , R II =R IX, R III =R VIII , R IV =R VII , and R V =R VI It is. [ka] [ka] [ka] [ka] [ka]

[0242] The general procedure for synthetic AAV5 is as follows. [ka]

[0243] 1,3-Dibromo-2,5-dichlorobenzene (CAS: 81067-41-6, 1.00 equiv.), E4 (2.10 equiv.), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 , CAS: 13716-12-6, 0.04 equivalents), and sodium tert-butoxide (NaO t Bu, 4.00 equiv.) in toluene under nitrogen atmosphere at 85 °C until completion. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the layers are separated. The combined organic layers are washed with MgSO 4The mixture is dried over 100 ml of water and the solvent is then removed under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give I4 as a solid.

[0244] The general procedure for synthetic AAV6 is as follows. [ka]

[0245] I4 (1.00 equivalent), E5 (2.10 equivalent), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equiv., CAS: 51364-51-3), tri-tert-butylphosphine tetrafluoroborate (0.04 equiv., P( t Bu) 3 HBF 4 , CAS: 131274-22-1), and sodium tert-butoxide (NaO t Bu; 4.00 equiv.) in toluene under nitrogen atmosphere is stirred at 110° C. until completion. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the layers are separated. The combined organic layer is washed with MgSO 4 The mixture is dried over 100 ml of water and the solvent is then removed under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give I5 as a solid.

[0246] The general procedure for synthetic AAV7 is as follows. [ka]

[0247] I5 (1.00 equiv.) was dissolved in tert-butylbenzene under a nitrogen atmosphere and cooled to -20°C, or dissolved in tert-butylbenzene and cooled to -10°C, and then tBuLi (2.20 equiv., CAS: 594-19-4) is added and the reaction mixture is stirred at 0° C. for 30 min. After complete lithiation, trimethylborate (6.00 equiv., CAS: 121-43-7) is added and the reaction mixture is stirred under reflux at 55° C. overnight. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine and the layers are separated. The combined organic layers are washed with MgSO 4 The mixture is dried over 100 ml of water and the solvent is then removed under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give I6 as a solid.

[0248] The general procedure for synthetic AAV8 is as follows. [ka]

[0249] I6 (1.00 equiv.), N,N-diisopropylethylamine (10.0 equiv., CAS: 7087-68-5) and AlCl 3 (10.0 equiv., CAS: 7446-70-0) is stirred in chlorobenzene under nitrogen atmosphere at 110°C until completion. After completion, the reaction is quenched by adding water at 0°C. The phases are then separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are washed with water and brine and diluted with MgSO 4 The mixture is dried at 40° C., filtered and then concentrated under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give I7 as a solid.

[0250] The general procedure for synthetic AAV9 is as follows. [ka]

[0251] I7 (1.00 equiv), E6 (6.00 equiv), palladium(II) acetate (CAS: 3375-31-3, 0.06 equiv), X-Phos (CAS: 564483-18-7, 0.24 equiv) and tripotassium phosphate (6.00 equiv) are stirred in dioxane / toluene 1:1 under nitrogen atmosphere at 100 °C until complete. After cooling to room temperature (rt), the reaction mixture is extracted with DCM and brine and the phases are separated. The combined organic layer is washed with MgSO 4 The mixture is dried over 100 ml of water and the solvent is then removed under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give P1 as a solid.

[0252] General synthetic scheme III General synthetic scheme III provides a synthetic scheme for organic molecules according to the invention, I =R X , R II =R IX , R III =R VIII , R IV =R VII , and R V =R VI , and R A =R D and R B =R C . [ka] [ka]

[0253] The final synthetic step of general scheme III from I2 to P1 is carried out under similar conditions as described for AAV3 and AAV4.

[0254] The general procedure for synthetic AAV10 is as follows. [ka]

[0255] E6 (1.00 equivalents), E7 (1.05 equivalents), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 , CAS: 13716-12-6, 0.04 equivalents), and sodium tert-butoxide (NaO t Bu, 1.50 equiv.) in toluene under nitrogen atmosphere is stirred at 80 °C until complete. After cooling to room temperature (rt), the reaction mixture is extracted with ethyl acetate and brine, and the layers are separated. The combined organic layers are washed with MgSO 4 The mixture is dried over 100 ml of water and the solvent is then removed under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give I8 as a solid.

[0256] The general procedure for synthetic AAV11 is as follows. [ka]

[0257] E8 (1.00 equivalent), I8 (2.20 equivalent), tris(dibenzylideneacetone)dipalladium Pd 2 (dba) 3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine (P( t Bu) 3 , CAS: 13716-12-6, 0.04 equivalents), and sodium tert-butoxide (NaO t Bu, 4.00 equiv.) in toluene under nitrogen atmosphere is stirred at 110 °C until complete. After cooling to room temperature (rt), the reaction mixture is extracted with toluene and brine, and the layers are separated. The combined organic layers are washed with MgSO 4 The mixture is dried over 100 ml of water and the solvent is then removed under reduced pressure. The resulting crude product is purified by recrystallization and column chromatography to give I2 as a solid.

[0258] The final synthetic step of general scheme III from I2 to P1 is carried out under similar conditions as described for AAV3 and AAV4.

[0259] General procedure for synthetic AAV12 (R XI = carbazole derivative) is as follows. [ka]

[0260] N 2 Under atmosphere, a two-neck flask is charged with 1-chloro-2,6-dibromo-4-fluorobenzene [179897-90-6] (1.00 equiv.), potassium triphosphate [7778-53-2] (3.00 equiv.), and the corresponding carbazole derivative (1.05 equiv.). Dry DMSO (4 mL / mmol of aryl fluoride) is added and the resulting suspension is heated at 100 °C until completion. After cooling to rt, the mixture is poured into a beaker of water (400 mL). The precipitate is filtered and washed liberally with water followed by ethanol. The filter cake is collected and purified by recrystallization to give the desired product E8 as a solid.

[0261] Cyclic Voltammetry Cyclic voltammograms were performed in dichloromethane or a suitable solvent for 10 -3 The measurements are performed from a solution containing an organic molecule at a concentration of 1000 mol / L and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). The measurements are performed at room temperature under a nitrogen atmosphere using a three-electrode assembly (working and counter electrodes: Pt wires, reference electrode: Pt wire) and FeCp as an internal standard. 2 / FeCp 2 + The HOMO data were corrected using ferrocene as an internal standard against a saturated calomel electrode (SCE).

[0262] Density functional theory calculations Molecular structures are optimized using the BP86 functional method and the unit resolution method (RI). Excitation energies are calculated using the (BP86) optimized structure using the time-dependent DFT (TD-DFT) method. B3LYP functions are used to calculate orbitals and excited state energies. Def2-SVP based set and m4-grid for numerical integration are used. The Turbomole program package is used for all calculations.

[0263] optical physical measurements Sample pretreatment: spin coating Equipment: Spin150, SPS euro. The sample concentration was 10 mg / ml and was dissolved in a suitable solvent. Program: 1) 400 U / min for 3 sec, 1000 U / min for 20 sec at 1000 Upm / sec, 3) 4000 U / min for 10 sec at 1000 Upm / sec. After coating, the film is dried at 70° C. for 1 min.

[0264] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC) Steady-state emission spectroscopy is measured on a Horiba FluoroMax-4 equipped with a 150W Xenon-Arc lamp, excitation and emission monochromators, and a Hamamatsu R928 photomultiplier tube with time-correlated single photon counting options. Emission and excitation spectra are corrected using standard correction fits.

[0265] The same system is utilized to determine excited state lifetimes using the TCSPC method with an FM-2013 instrument and a Horiba Yvon TCSPC hub.

[0266] Excitation light source: NanoLED 370 (wavelength: 371 nm, pulse width: 1.1 ns) NanoLED 290 (wavelength: 294nm, pulse width: <1ns) SpectraLED 310 (wavelength: 314nm) SpectraLED 355 (wavelength: 355nm)

[0267] Data analysis (exponential fitting) is performed using the software suite DataStation and DAS6 analysis software. The fit is determined using the Chi-square test.

[0268] Photoluminescence quantum yield measurement For photoluminescence quantum yield (PLQY) measurements, an absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.

[0269] Emission maxima are given in nm, quantum yields Φ in %, and CIE coordinates as x,y values. The PLQY is determined using the following protocol. 1) Quality assurance: Anthracene in ethanol (known concentration) is used as a reference material 2) Excitation wavelength: determine the maximum absorption of the organic molecule and use this wavelength to excite the molecule 3) Measurement The quantum yield is measured on a solution or film sample under nitrogen atmosphere and is calculated using the following formula:

number

[0270] Fabrication and characterization of optoelectronic devices Optoelectronic devices, especially OLED devices, comprising organic molecules according to the invention can be produced by vacuum deposition. If a layer contains one or more compounds, the weight percentage of one or more compounds is given in %. The total weight percentage value adds up to 100%, therefore, if no value is given, the fraction of this compound is equal to the difference between the given value and 100%.

[0271] The non-fully optimized OLEDs are characterized using standard methods as well as measuring the external quantum efficiency (in %) in dependence on intensity calculated using electroluminescence spectra, light detected by a photodiode, and current. The OLED device lifetime is extracted from the change in luminance during operation at constant current density. The LT50 value corresponds to the time when the measured luminance is reduced to 50% of the initial luminance, similarly LT80 corresponds to the time point when the measured luminance is reduced to 80% of the initial luminance, and LT95 corresponds to the time point when the measured luminance is reduced to 95% of the initial luminance.

[0272] Carry out accelerated lifetime measurements (e.g., by applying a higher current density), e.g., 500 cd / m 2 The LT80 value at is determined using the following equation:

number

[0273] The value corresponds to the average of several pixels (usually 2-8) and the standard deviation between these pixels is given.

[0274] HPLC-MS: HPLC-MS analyses are carried out on an Agilent (1100 series) HPLC with an MS-detector (Thermo LTQ XL).

[0275] For example, an example of a typical HPLC method is as follows: a reversed-phase column 4.6 mm x 150 mm, particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95 Å C18, 4.6x150 mm, 3.5 μm HPLC column) is used for HPLC. The HPLC-MS measurements are carried out at room temperature (rt) following a gradient. [Table 1]

[0276] The following solvent mixtures are used: [Table 2]

[0277] An injection volume of 5 μL is taken for the measurement from a solution containing analyte at a concentration of 0.5 mg / mL.

[0278] Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source in either positive (APCI+) or negative (APCI-) ionization mode.

[0279] Example 1 [ka]

[0280] Example 1 was synthesized as follows: AAV5 (yield 84%), 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine (CAS: 92050-16-3) was used as reactant E4. AAV6 (yield 99%), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (CAS: 27452-17-1) were used as reactant E5. AAV7 (yield 54%) AAV8 (yield 51%) AAV9 (yield 93%), methaneboronic acid (CAS: 13061-96-6) were used as reactant E6.

[0281] MS (HPLC-MS), m / z (retention time): 875.9 (9.38 minutes)

[0282] The emission maximum of Example 1 (2 wt. % in PMMA) is 459 nm, the full width at half maximum (FWHM) is 0.16 eV, and the CIEx and CIEy coordinates are 0.14 and 0.10, respectively. The photoluminescence quantum yield (PLQY) is 79%.

[0283] Example 2 [ka]

[0284] Example 2 was synthesized as follows: For AAV1 (yield 83%), 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) was used as reactant E1, and 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine (CAS: 92050-16-3) was used as reactant E2. AAV2 (yield 83%), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (CAS: 27452-17-1) was used as reactant E3. AAV3 (0.2% yield), produced as follows: I3. [ka] AAV4 (yield 65%) and reactant I3 were used. [ka] Reactant I3

[0285] MS (HPLC-MS), m / z (retention time): 861.9 (9.57 minutes)

[0286] Example 2 has an emission maximum (2 wt % in PMMA) of 461 nm with a full width at half maximum (FWHM) of 0.16 eV, and CIEx and CIEy coordinates of 0.13 and 0.10, respectively.

[0287] The photoluminescence quantum yield (PLQY) is 67%.

[0288] Example 3 [ka]

[0289] Example 3 was synthesized as follows: AAV1 (yield 47%), 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) was used as reactant E1, and 5-aminoindan (CAS: 24425-40-9) was used as reactant E2. AAV2 (yield 42%), 5-bromo-1,3-dichloro-2-methylbenzene (CAS: 204930-37-0) were used as reactant E3. AAV2-a (48% yield), the following was used as I2-a, and phenylboronic acid (CAS: 98-80-6) was used as reactant E2-a.

[0290] [ka] AAV3, AAV4.

[0291] MS (HPLC-MS), m / z (retention time): 833.6 (7.70 minutes)

[0292] The emission maximum of Example 3 (2 wt. % in PMMA) is 457 nm, the full width at half maximum (FWHM) is 0.15 eV, and the CIEx and CIEy coordinates are 0.14 and 0.09, respectively. The photoluminescence quantum yield (PLQY) is 70%.

[0293] Example 4 [ka]

[0294] Example 4 was synthesized as follows: AAV10 (yield 80%), 1-bromo-3,5-di-tert-butylbenzene (CAS: 22385-77-9) was used as reactant E6, and 5,6,7,8-tetrahydro-2-naphthylamine (CAS: 2217-43-8) was used as reactant E7. AAV11 (yield 66%) and 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) were used as reactant E8. AAV3, AAV4.

[0295] MS (HPLC-MS), m / z (retention time): 753.8 (8.74 minutes)

[0296] Example 4 has an emission maximum (2% by weight of PMMA) of 463 nm, a full width at half maximum (FWHM) of 0.16 eV, and CIEx and CIEy coordinates of 0.13 and 0.12, respectively.

[0297] Example 5 [ka]

[0298] Example 5 was synthesized as follows: AAV1 (yield 47%), 1,3-dibromo-2-chlorobenzene (CAS: 19230-27-4) was used as reactant E1, and 5-aminoindan (CAS: 24425-40-9) was used as reactant E2. AAV2 (87% yield), 1-bromo-3,5-di-tert-butylbenzene (CAS: 22385-77-9) was used as reactant E3. AAV3 (yield 21%) AAV4 (yield 13%).

[0299] MS (HPLC-MS), m / z (retention time): 725.7 (8.41 minutes)

[0300] The emission maximum of Example 5 (2 wt % in PMMA) is 459 nm, the full width at half maximum (FWHM) is 0.16 eV, and the CIEx and CIEy coordinates are 0.14 and 0.10, respectively.

[0301] The photoluminescence quantum yield (PLQY) is 71%.

[0302] Example 6 [ka]

[0303] Example 6 was synthesized as follows: Carbazole (CAS: 86-74-8) was used as a carbazole derivative to obtain AAV12 (yield 78%) and E8. AAV10 (yield 80%), 1-bromo-3,5-di-tert-butylbenzene (CAS: 22385-77-9) was used as reactant E6, and 5,6,7,8-tetrahydro-2-naphthylamine (CAS: 2217-43-8) was used as reactant E7. AAV11 (yield 68%) AAV3, AAV4.

[0304] MS (HPLC-MS), m / z (retention time): 918.80 (9.11 minutes)

[0305] Example 6 has an emission maximum (2 wt % in PMMA) of 453 nm with a full width at half maximum (FWHM) of 0.14 eV, and CIEx and CIEy coordinates of 0.14 and 0.07, respectively.

[0306] The photoluminescence quantum yield (PLQY) is 79%.

[0307] Example D1 Example 1 was tested in an OLED D1 made with the following layer structure: [Table 3]

[0308] [ka]

[0309] Device D1 provides 1000cd / m 2 An external quantum efficiency (EQE) of 11.8% was obtained at 3.7 V. The emission maximum is at 464 nm with a FWHM of 24 nm at 3.7 V. The corresponding CIEx value is 0.13 and CIEy value is 0.09.

[0310] Example D2 Example 2 was tested in an OLED D2 constructed with the following layer structure: [Table 4]

[0311] [ka] MAT5

[0312] Device D2 provides 1000cd / m 2 An external quantum efficiency (EQE) of 12.2% was obtained at 3.6 V. The emission maximum is at 466 nm with a FWHM of 24 nm at 3.6 V. The corresponding CIEx value is 0.13 and CIEy value is 0.10.

[0313] Example D3 Example 3 was tested in an OLED D3 made with the following layer structure: [Table 5]

[0314] 1000cd / m by device D3 2An external quantum efficiency (EQE) of 11.4% was obtained at 3.5 V. The emission maximum is at 462 nm with a FWHM of 24 nm at 3.5 V. The corresponding CIEx value is 0.13 and CIEy value is 0.09.

[0315] Example D4 Example 4 was tested in an OLED D4 constructed with the following layer structure: [Table 6]

[0316] 1000cd / m with device D4 2 An external quantum efficiency (EQE) of 11.7% was obtained at 3.5 V. The emission maximum is at 466 nm with a FWHM of 24 nm at 3.5 V. The corresponding CIEx value is 0.13 and CIEy value is 0.11.

[0317] Example D5 Example 5 was tested in an OLED D5 constructed with the following layer structure: [Table 7]

[0318] 1000cd / m by device D5 2 An external quantum efficiency (EQE) of 11.3% was obtained at 3.5 V. The emission maximum is at 462 nm with a FWHM of 24 nm at 3.5 V. The corresponding CIEx value is 0.13 and CIEy value is 0.09.

[0319] Example D6 Example 6 was tested in an OLED D6 made with the following layer structure: [Table 8]

[0320] Device D6 provides 1000cd / m 2An external quantum efficiency (EQE) of 10.5% was obtained at 3.5 V. The emission maximum is at 456 nm with a FWHM of 22 nm at 3.5 V. The corresponding CIEx value is 0.14 and CIEy value is 0.06.

[0321] Additional Examples of Organic Molecules of the Invention In the structures, the abbreviation Cbz denotes a bound carbazole group, and the following materials are equivalent: [ka] [ka]

[0322] moreover, t Bu denotes an attached tertiary butyl group, therefore the following materials are equivalent: [ka] [ka]

[0323] Additionally, when Ph appears in a structure, it refers to a bound phenyl group, whereby the following materials are equivalent: [ka] [ka]

[0324] [ka]

[0325] [ka]

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Claims

1. An organic molecule comprising the structure of Formula I, 【Chemistry 1】 Formula I During the ceremony, R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ , R Ｘ , R ＸＩ , R Ａ , R Ｂ , R Ｃ and R Ｄ but, Hydrogen, deuterium, halogens, C １ ~C １２ - alkyl, Optionally, one or more hydrogen atoms may be R ５ independently substituted by C ６ ~C １８ -aryl, Optionally, one or more hydrogen atoms may be R ５ and C ３ ~C １５ Heteroaryl, Optionally, one or more hydrogen atoms may be R ５ and independently selected from the group consisting of: R ５ At each occurrence, Hydrogen, deuterium, halogens, C １ ~C １２ - alkyl, Optionally, one or more hydrogen atoms may be R ６ independently substituted by C ６ ~C １８ -aryl, Optionally, one or more hydrogen atoms may be R ６ and C ３ ~C １５ Heteroaryl, Optionally, one or more hydrogen atoms may be R ６ and independently selected from the group consisting of: R ６ At each occurrence, Hydrogen, deuterium, halogens, C １ ~C １２ -alkyl, C ６ ~C １８ -aryl, Optionally, one or more hydrogen atoms are C １ ~C ５ - independently substituted by alkyl substituents, and C ３ ~C １５ Heteroaryl, Optionally, one or more hydrogen atoms are C １ ~C ５ - independently substituted with alkyl substituents; R Ｉ , R ＩＩ , R ＩＩＩ , R ＩＶ , R Ｖ , R ＶＩ , R ＶＩＩ , R ＶＩＩＩ , R ＩＸ , R Ｘ , R Ａ , R Ｂ , R Ｃ , R Ｄ any two adjacent may form a monocyclic ring system having 5 to 8 C atoms, Optionally, hydrogen can be R ６ are independently substituted by At least R Ａ and R Ｂ together form a monocyclic ring system having 5 to 8 C atoms, Optionally, hydrogen can be R ６ are independently substituted by and, optionally, hydrogen is independently replaced by deuterium or a halogen; The structure of formula I is a structure of formula Ie-1, formula Ia-2, or formula Ib-2, 【Chemistry 2】 Formula Ie-1 【Chemistry 3】 Formula Ia-2 【Chemistry 4】 Formula Ib-2 R II , R IV , R IX and R VII in formula Ia-2 are independently selected from C 6 -C 18 -aryl; R II , R IV , R IX and R VII in formula Ib-2 are independently selected from the group consisting of hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, C 3 -C 15 -heteroaryl; R XI in formula Ia-2 is selected from C 3 -C 15 -heteroaryl; An organic molecule wherein R XI in formula Ie-1 and formula Ib-2 is independently selected from the group consisting of hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, C 3 -C 15 -heteroaryl.

2. The organic molecule described in claim 1, wherein the structure of formula Ie-1 includes a structure of formula Ic-3. 【Chemistry 5】 Formula Ic-3

3. In the formula Ia-2, R I , R III , R V , R VI , R VIII , and R X are each independently hydrogen, deuterium, halogen, C １ ~C １２ -alkyl, C ６ ~C １８ -aryl, Optionally, one or more hydrogen atoms are C １ ~C ５ - independently substituted by alkyl substituents, and C ３ ~C １５ Heteroaryl, Optionally, one or more hydrogen atoms are C １ -C ５ - independently substituted with alkyl substituents; Optionally, each hydrogen is replaced independently by Me; R I , R II , R III , R IV , R V , R VI , R VIII and R X in formula Ib-2 are hydrogen, deuterium, halogen, C 1 -C 12 -alkyl, C 6 -C 18 -aryl, Optionally, one or more hydrogen atoms are independently replaced by a C 1 -C 5 -alkyl substituent; and C 3 -C 15 -heteroaryl, Optionally, one or more hydrogen atoms are independently replaced by a C 1 -C 5 -alkyl substituent; any two adjacent R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X form a monocyclic ring system having 5 to 8 C atoms, 2. The organic molecule of claim 1, wherein each hydrogen may be optionally replaced, independently of the other, by Me.

4. In formula Ia-2, R I , R V , R VI , and R X are each independently hydrogen, deuterium, halogen, Me, ｔ R IV is independently selected from the group consisting of Bu, Ph, cyclohexyl, and carbazole; R IV is selected from Ph; R I , R IV , R V , R VI , and R X in formula Ib-2 are independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl, and carbazole; R XI in formula Ie-1 and formula Ib-2 is independently selected from the group consisting of hydrogen, deuterium, halogen, Me, t Bu, Ph, cyclohexyl, and carbazole; The organic molecule according to any one of claims 1 to 3, wherein R XI in formula Ia-2 is selected from carbazole.

5. R Ｉ , R Ｖ , R ＶＩ and R Ｘ The organic molecule according to any one of claims 1 to 4, wherein is hydrogen.

6. R in formula Ie-1 and formula Ib-2 ＸＩ The organic molecule according to any one of claims 1 to 5, wherein is Me.

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

8. The optoelectronic device comprises: Organic Light Emitting Diodes (OLEDs); - light-emitting electrochemical cells, OLED sensor, - organic diodes, ・Organic solar cells, ・ Organic transistors, - Organic field effect transistors, Organic lasers, and - a down-conversion element.

9. (a) an organic molecule according to any one of claims 1 to 6, in particular in the form of an emitter and / or host, and (b) an emitter and / or host material different from the organic molecule; and (c) A composition, optionally including a dye and / or a solvent.

10. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 6 or a composition according to claim 9, in particular in the form of a device selected from the group consisting of organic light emitting diodes (OLEDs), light emitting electrochemical cells, OLED sensors, organic diodes, organic solar cells, organic transistors, organic field effect transistors, organic lasers and down conversion elements.

11. - substrate, an anode, and a cathode, said anode or said cathode being arranged on said substrate, and An optoelectronic device according to claim 10, comprising: a light-emitting layer disposed between said anode and said cathode, said light-emitting layer comprising said organic molecules or said composition.

12. A method for manufacturing an optoelectronic device, in which an organic molecule according to any of claims 1 to 6 or a composition according to claim 9 is used, comprising processing said organic molecule, in particular by a vacuum deposition method or from solution.

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