Organic molecules for optoelectronic devices

Abstract

The invention relates to an organic molecule for use in an optoelectronic device. The organic molecule has a structure of formula (I): wherein X is selected from a group consisting of a direct bond, NR 1 、O、S、SiR 1 R 2 and CR 1 R 2 Y is selected from the group consisting of a direct bond, NR 3 、O、S、SiR 3 R 4 and CR 3 R 4 The group consisting of: 1 , R 2 , R 3 and R 4 independently selected from the group consisting of: hydrogen; deuterium; N(R 5 ) 2 ;OR 5 SR 5 ;Si(R 5 ) 3 ; B(OR 5 ) 2 ;OSO 2 R 5 CF 3 ;CN;halogen;C 1 ‑C 40 Alkyl; C 1 ‑C 40 Alkoxy; C 1 ‑C 40 Thioalkoxy; C 2 ‑C 40 Alkenyl; C 2 ‑C 40 Alkynyl; C 6 ‑C 60 Aryl; and C 3 ‑C 57 Heteroaryl.

Description

Technical Field

[0001] The invention relates to organic molecules and the use of organic molecules in organic light emitting diodes (OLEDs) and in other optoelectronic devices. Similar compounds are known from CN109438446A and CN110204565A. Background Art

[0002] The use of organic molecules in optoelectronic devices is being actively developed. Summary of the invention

[0003] The object of the present invention is to provide organic molecules suitable for use in optoelectronic devices.

[0004] The object is achieved by providing an invention of a novel organic molecule.

[0005] The inventive organic molecule is preferably a pure organic molecule, i.e., in contrast to known metal complexes for optoelectronic devices, the organic molecule does not contain any metal ions. Therefore, according to the present invention, preferably, the organic molecule does not contain metal atoms or metal ions. However, the organic molecule may include metalloids (particularly B, Si, Sn, Se and / or Ge).

[0006] The organic molecules exhibit emission maxima in the sky blue, green or yellow spectral range. Specifically, the photoluminescence quantum yield of the organic molecules according to the invention is 10% or more. Specifically, the organic molecules of the invention exhibit thermally activated delayed fluorescence (TADF). The use of the organic molecules according to the invention in optoelectronic devices (e.g., organic light emitting diodes (OLEDs)) leads to higher efficiency of the optoelectronic devices. The corresponding OLED has a higher stability than an OLED with known emitter materials and comparable colors, and / or by adopting the organic molecules according to the invention in an OLED display, a more accurate reproduction of actually visible colors (i.e., a higher resolution of displayed images) is achieved. Specifically, the organic molecules can be used in combination with fluorescent emitters to achieve so-called superfluorescence.

[0007] The organic molecule according to the invention comprises or consists of a structure of formula I:

[0008]

[0009] in,

[0010] X is selected from the group consisting of direct bonds, NR 1 、O、S、SiR 1 R 2 and CR 1 R 2 The group composed of;

[0011] Y is selected from the group consisting of direct bonds, NR3 、O、S、SiR 3 R 4 and CR 3 R 4 The group composed of;

[0012] R 1 , R 2 , R 3 and R 4 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; N(R 5 ) 2 ;OR 5 SR 5 ;Si(R 5 ) 3 ; B(OR 5 ) 2 ;OSO 2 R 5 CF 3 ;CN;halogen;C 1 -C 40 Alkyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 5 C=CR 5 、C≡C、Si(R 5 ) 2 , Ge(R 5 ) 2 Sn(R 5 ) 2 ,C=O,C=S,C=Se,C=NR 5 ,P(=O)(R 5 ), SO, SO 2 NR 5 , O, S or CONR 5 Replace; C 1 -C 40 Alkoxy, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 5 C=CR 5 、C≡C、Si(R 5 ) 2 , Ge(R 5 ) 2 Sn(R 5 ) 2 ,C=O,C=S,C=Se,C=NR 5 ,P(=O)(R 5 ), SO, SO2 NR 5 , O, S or CONR 5 Replace; C 1 -C 40 Thioalkoxy, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 5 C=CR 5 、C≡C、Si(R 5 ) 2 , Ge(R 5 ) 2 Sn(R 5 ) 2 ,C=O,C=S,C=Se,C=NR 5 ,P(=O)(R 5 ), SO, SO 2 NR 5 , O, S or CONR 5 Replace; C 2 -C 40 Alkenyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 5 C=CR 5 、C≡C、Si(R 5 ) 2 , Ge(R 5 ) 2 Sn(R 5 ) 2 ,C=O,C=S,C=Se,C=NR 5 ,P(=O)(R 5 ), SO, SO 2 NR 5 , O, S or CONR 5 Replace; C 2 -C 40 Alkynyl, optionally substituted with one or more substituents R 5 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 5 C=CR 5 、C≡C、Si(R 5 ) 2 , Ge(R 5 ) 2 Sn(R 5 ) 2 ,C=O,C=S,C=Se,C=NR 5,P(=O)(R 5 ), SO, SO 2 NR 5 , O, S or CONR 5 Replace; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 5 ; wherein the groups R positioned adjacent to each other 5 optionally combined with each other to form optionally substituted with one or more C 1 -C 5 Alkyl substituent, deuterium, halogen, CN or CF 3 An aromatic or heteroaromatic ring;

[0013] Wherein, X and Y do not both represent direct bonds;

[0014] R 5 is independently selected from the group consisting of: hydrogen; deuterium; N(R 6 ) 2 ;OR 6 SR 6 ;Si(R 6 ) 3 ; B(OR 6 ) 2 ;OSO 2 R 6 CF 3 ;CN;halogen;C 1 -C 40 Alkyl, optionally substituted with one or more substituents R 6 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 6 C=CR 6 、C≡C、Si(R 6 ) 2 , Ge(R 6 ) 2 Sn(R 6 ) 2 ,C=O,C=S,C=Se,C=NR 6 ,P(=O)(R 6 ), SO, SO 2 NR 6 , O, S or CONR 6 Replace; C 1 -C 40 Alkoxy, optionally substituted with one or more substituents R6 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 6 C=CR 6 、C≡C、Si(R 6 ) 2 , Ge(R 6 ) 2 Sn(R 6 ) 2 ,C=O,C=S,C=Se,C=NR 6 ,P(=O)(R 6 ), SO, SO 2 NR 6 , O, S or CONR 6 Replace; C 1 -C 40 Thioalkoxy, optionally substituted with one or more substituents R 6 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 6 C=CR 6 、C≡C、Si(R 6 ) 2 , Ge(R 6 ) 2 Sn(R 6 ) 2 ,C=O,C=S,C=Se,C=NR 6 ,P(=O)(R 6 ), SO, SO 2 NR 6 , O, S or CONR 6 Replace; C 2 -C 40 Alkenyl, optionally substituted with one or more substituents R 6 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 6 C=CR 6 、C≡C、Si(R 6 ) 2 , Ge(R 6 ) 2 Sn(R 6 ) 2 ,C=O,C=S,C=Se,C=NR 6 ,P(=O)(R 6 ), SO, SO 2 NR 6 , O, S or CONR 6 Replace; C 2 -C40 Alkynyl, optionally substituted with one or more substituents R 6 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 6 C=CR 6 、C≡C、Si(R 6 ) 2 , Ge(R 6 ) 2 Sn(R 6 ) 2 ,C=O,C=S,C=Se,C=NR 6 ,P(=O)(R 6 ), SO, SO 2 NR 6 , O, S or CONR 6 Replace; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 6 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 6 ; wherein the groups R positioned adjacent to each other 5 optionally combined with each other to form optionally substituted with one or more C 1 -C 5 Alkyl substituent, deuterium, halogen, CN or CF 3 An aromatic or heteroaromatic ring.

[0015] R 6 is independently selected from the group consisting of: hydrogen; deuterium; halogen; OPh; SPh; CF 3 ;CN;Si(C 1 -C 5 alkyl) 3 ;Si(Ph) 3 ; C 1 -C 5 Alkyl, wherein, optionally, one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 1 -C 5 Alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 1 -C 5 Thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 2 -C 5Alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 2 -C 5 Alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 6 -C 18 Aryl, optionally substituted with one or more C 1 -C 5 Alkyl substituent; C 3 -C 17 Heteroaryl, optionally substituted with one or more C 1 -C 5 Alkyl substituent; N(C 6 -C 18 Aryl) 2 ; N(C 3 -C 17 Heteroaryl) 2 ; and N(C 3 -C 17 Heteroaryl) (C 6 -C 18 aryl),

[0016] R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV , R XV and R XVI independently selected from the group consisting of: hydrogen; deuterium; N(R 7 ) 2 ;OR 7 SR 7 ;Si(R 7 ) 3 ; B(OR 7 ) 2 ;OSO 2 R 7 CF 3 ;CN;halogen;C 1 -C 40 Alkyl, optionally substituted with one or more substituents R 7 , and wherein one or more non-adjacent CH2 The group may be optionally replaced by R 7 C=CR 7 、C≡C、Si(R 7 ) 2 , Ge(R 7 ) 2 Sn(R 7 ) 2 ,C=O,C=S,C=Se,C=NR 7 ,P(=O)(R 7 ), SO, SO 2 NR 7 , O, S or CONR 7 Replace; C 1 -C 40 Alkoxy, optionally substituted with one or more substituents R 7 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 7 C=CR 7 、C≡C、Si(R 7 ) 2 , Ge(R 7 ) 2 Sn(R 7 ) 2 ,C=O,C=S,C=Se,C=NR 7 ,P(=O)(R 7 ), SO, SO 2 NR 7 , O, S or CONR 7 Replace; C 1 -C 40 Thioalkoxy, optionally substituted with one or more substituents R 7 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 7 C=CR 7 、C≡C、Si(R 7 ) 2 , Ge(R 7 ) 2 Sn(R 7 ) 2 ,C=O,C=S,C=Se,C=NR 7 ,P(=O)(R 7 ), SO, SO 2 NR 7 , O, S or CONR 7 Replace; C 2 -C 40 Alkenyl, optionally substituted with one or more substituents R7 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 7 C=CR 7 、C≡C、Si(R 7 ) 2 , Ge(R 7 ) 2 Sn(R 7 ) 2 ,C=O,C=S,C=Se,C=NR 7 ,P(=O)(R 7 ), SO, SO 2 NR 7 , O, S or CONR 7 Replace; C 2 -C 40 Alkynyl, optionally substituted with one or more substituents R 7 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 7 C=CR 7 、C≡C、Si(R 7 ) 2 , Ge(R 7 ) 2 Sn(R 7 ) 2 ,C=O,C=S,C=Se,C=NR 7 ,P(=O)(R 7 ), SO, SO 2 NR 7 , O, S or CONR 7 Replace; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 7 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 7 ;

[0017] The groups R located adjacent to each other I To R IV optionally combined with each other to form optionally substituted with one or more C 1 -C 5 Alkyl substituent, deuterium, halogen, CN or CF 3 An aromatic or heteroaromatic ring;

[0018] The groups R located adjacent to each other V To R VIIIoptionally combined with each other to form optionally substituted with one or more C 1 -C 5 Alkyl substituent, deuterium, halogen, CN or CF 3 An aromatic or heteroaromatic ring;

[0019] The groups R located adjacent to each other IX To R XII optionally combined with each other to form optionally substituted with one or more C 1 -C 5 Alkyl substituent, deuterium, halogen, CN or CF 3 An aromatic or heteroaromatic ring;

[0020] The groups R located adjacent to each other XIII To R XVI optionally combined with each other to form optionally substituted with one or more C 1 -C 5 Alkyl substituent, deuterium, halogen, CN or CF 3 An aromatic or heteroaromatic ring.

[0021] R 7 Selected from the group consisting of: hydrogen; deuterium; N(R 8 ) 2 ;OR 8 SR 8 ;Si(R 8 ) 3 ; B(OR 8 ) 2 ;OSO 2 R 8 CF 3 ;CN;halogen;C 1 -C 40 Alkyl, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 ) 2 , Ge(R 8 ) 2 Sn(R 8 ) 2 ,C=O,C=S,C=Se,C=NR 8 ,P(=O)(R 8 ), SO, SO 2 NR 8 , O, S or CONR 8 Replace; C 1 -C40 Alkoxy, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 ) 2 , Ge(R 8 ) 2 Sn(R 8 ) 2 ,C=O,C=S,C=Se,C=NR 8 ,P(=O)(R 8 ), SO, SO 2 NR 8 , O, S or CONR 8 Replace; C 1 -C 40 Thioalkoxy, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 ) 2 , Ge(R 8 ) 2 Sn(R 8 ) 2 ,C=O,C=S,C=Se,C=NR 8 ,P(=O)(R 8 ), SO, SO 2 NR 8 , O, S or CONR 8 Replace; C 2 -C 40 Alkenyl, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 ) 2 , Ge(R 8 ) 2 Sn(R 8 ) 2 ,C=O,C=S,C=Se,C=NR 8 ,P(=O)(R 8 ), SO, SO 2 NR 8 , O, S or CONR8 Replace; C 2 -C 40 Alkynyl, optionally substituted with one or more substituents R 8 , and wherein one or more non-adjacent CH 2 The group may be optionally replaced by R 8 C=CR 8 、C≡C、Si(R 8 ) 2 , Ge(R 8 ) 2 Sn(R 8 ) 2 ,C=O,C=S,C=Se,C=NR 8 ,P(=O)(R 8 ), SO, SO 2 NR 8 , O, S or CONR 8 Replace; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 8 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 8 ;

[0022] R 8 is independently selected at each occurrence from the group consisting of: hydrogen; deuterium; halogen; OPh; SPh; CF 3 ;CN;Si(C 1 -C 5 alkyl) 3 ;Si(Ph) 3 ; C 1 -C 5 Alkyl, wherein, optionally, one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 1 -C 5 Alkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 1 -C 5 Thioalkoxy, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 2 -C 5 Alkenyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 2 -C 5Alkynyl, wherein optionally one or more hydrogen atoms are independently replaced by deuterium, halogen, CN or CF 3 Replace; C 6 -C 18 Aryl, optionally substituted with one or more C 1 -C 5 Alkyl substituent; C 3 -C 17 Heteroaryl, optionally substituted with one or more C 1 -C 5 Alkyl substituent; N(C 6 -C 18 Aryl) 2 ; N(C 3 -C 17 Heteroaryl) 2 ; and N(C 3 -C 17 Heteroaryl) (C 6 -C 18 Aryl);

[0023] Among them, the substituent R 1 , R 2 , R XIII , R XIV , R XV and / or R XVI Independently of each other, optionally with 1 , R 2 , R XIII , R XIV , R XV and R XVI One or more other substituents in the group of form a monocyclic or polycyclic aliphatic, aromatic and / or benzo-fused ring system; and

[0024] Among them, the substituent R 3 , R 4 , R IX , R X , R XI and / or R XII Independently of each other, optionally with 3 , R 4 , R IX , R X , R XI and R XII One or more other substituents in the group form a monocyclic or polycyclic aliphatic, aromatic and / or benzo-fused ring system.

[0025] In one embodiment, Y is selected from a group consisting of a direct bond, NR 3 、O、S、SiR 3 R 4 and CR3 R 4 The group is composed of; and the prerequisite is that if Y is CR 3 R 4 , then the substituent R 3 and R 4 Not from R 3 , R 4 , R IX , R X , R XI and R XII One or more of the other substituents in the group formed form a monocyclic or polycyclic aliphatic, aromatic and / or benzo-fused ring system.

[0026] In one embodiment, Y is selected from a group consisting of a direct bond, NR 3 , O and S.

[0027] In a preferred embodiment, Y is a direct bond.

[0028] In one embodiment, X is selected from a group consisting of a direct bond, NR 1 、O、S、SiR 1 R 2 and CR 1 R 2 The group is composed of; and the prerequisite is that if Y is CR 1 R 2 , then the substituent R 1 and R 2 Not from R 1 , R 2 , R XIII , R XIV , R XV and R XVI One or more of the other substituents in the group formed form a monocyclic or polycyclic aliphatic, aromatic and / or benzo-fused ring system.

[0029] In one embodiment, X is selected from a group consisting of a direct bond, NR 1 and SiR 1 R 2 Composed of groups.

[0030] In a preferred embodiment, X is selected from a group consisting of a direct bond and NR 1 Composed of groups.

[0031] Substituent R 1 , R 2 , R XIII , R XIV , R XV or R XVIindependently of one another, optionally bonded to one another via a single bond or by fusion, to one or more substituents R via a linker or a single bond or by fusion 1 , R 2 , R XIII , R XIV , R XV or R XVI Forming a monocyclic or polycyclic aliphatic, aromatic and / or benzo-fused ring system. 3 , R 4 , R IX , R X , R XI or R XII independently of one another, optionally bonded to one another via a single bond or by fusion, to one or more substituents R via a linker or a single bond or by fusion 3 , R 4 , R IX , R X , R XI or R XII Forming monocyclic or polycyclic aliphatic, aromatic and / or benzo-fused ring systems. Examples are listed below:

[0032]

[0033] In one embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of Formula I-1a, Formula I-1a-1, Formula I-1a-2, Formula I-1a-3, Formula I-1a-4 and Formula I-1a-5, or consists of a structure selected from the group consisting of Formula I-1a, Formula I-1a-1, Formula I-1a-2, Formula I-1a-3, Formula I-1a-4 and Formula I-1a-5:

[0034]

[0035]

[0036] In yet another embodiment of the invention, R I , R II , R III , R IV , R XIII , R XIV , R XV and R XVI independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; triazine group, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0037] In yet another embodiment of the invention, wherein R I , R II , R III , R IV , R XIII , R XIV , R XV and R XVI independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; and a triazine group, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph.

[0038] In yet another embodiment of the invention, wherein R V , R VI , R VII , RVIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; triazine group, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0039] In yet another embodiment of the invention, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF3 and Ph; and a triazine group, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph.

[0040] In a preferred embodiment of the invention, the organic molecule comprises or consists of the structure of formula I-1a:

[0041]

[0042] In another embodiment of the invention, the organic molecule comprises or consists of the structure of formula I-1b:

[0043]

[0044] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of formula 1-2:

[0045]

[0046] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula I or Formula I-1a, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;OPh;CMe 2 Ph; N(Ph) 2 ; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0047] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R V To R XII To form an aromatic ring or a heteroaromatic ring.

[0048] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula I-2b-1 to Formula I-2b-19, or consists of a structure selected from the group consisting of Formula I-2b-1 to Formula I-2b-19:

[0049]

[0050] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula I or Formula I-1a, wherein R V and R XII Not all represent hydrogen.

[0051] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula I or Formula I-1a, wherein R V and R XII Unlike hydrogen.

[0052] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula I or Formula I-1a, wherein R V =R XII and / or R X =R VII .

[0053] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula I or Formula I-1a, wherein R V =R XII And R X =R VII .

[0054] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula I or Formula I-1a, wherein R 1 , R 2 , R 3 and R 4 is independently selected at each occurrence from the group consisting of: hydrogen; C 1 -C 5 Alkyl, optionally substituted with one or more substituents R 5 ; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0055] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure of Formula Ia:

[0056]

[0057] in,

[0058] X 2 Selected from N, SiR 2 and CR 2 The group composed of;

[0059] Ring a represents: C 6 -C 18 An aromatic ring, wherein one or more hydrogen atoms are optionally independently replaced by R 5 Replacement; and C 3 -C 7 A heteroaromatic ring, wherein one or more hydrogen atoms are independently replaced by R 5 replace.

[0060] Z is selected from the direct bond, NR 7 、O、S、Si(R 7 ) 2 and C(R 7 ) 2 Composed of groups.

[0061] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula Ia-1a:

[0062]

[0063] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ia or Formula Ia-1a, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;OPh;CMe 2 Ph; N(Ph) 2 ; and Ph, optionally substituted with independently selected from Me, i Pr,t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0064] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R V To R XII To form an aromatic ring or a heteroaromatic ring.

[0065] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ia-1a-1 to Formula Ia-1a-19, or consists of a structure selected from the group consisting of Formula Ia-1a-1 to Formula Ia-1a-19:

[0066]

[0067] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ia or Formula Ia-1a, wherein R V and R XII Not all represent hydrogen.

[0068] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ia or Formula Ia-1a, wherein R V and R XII Unlike hydrogen.

[0069] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ia or Formula Ia-1a, wherein R V =R XII and / or R X =R VII .

[0070] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ia or Formula Ia-1a, wherein R V =R XII And R X =R VII .

[0071] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ia or Formula Ia-1a, wherein R 1 , R 2 , R 3 and R 4is independently selected at each occurrence from the group consisting of: hydrogen; C 1 -C 5 Alkyl, optionally substituted with one or more substituents R 5 ; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0072] In one embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ia-1b, Formula Ia-1b-2 and Formula Ia-1b-3, or consists of a structure selected from the group consisting of Formula Ia-1b, Formula Ia-1b-2 and Formula Ia-1b-3:

[0073]

[0074] In a preferred embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ia-1b:

[0075]

[0076] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ia-1c:

[0077]

[0078] In one embodiment of the invention, the organic molecule comprises or consists of a structure of Formula Ia-2a:

[0079]

[0080] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ia-2b:

[0081]

[0082] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ia-2c:

[0083]

[0084] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of Formula Ia-3:

[0085]

[0086] In one embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ib to Formula Ib-8, or consists of a structure selected from the group consisting of Formula Ib to Formula Ib-8:

[0087]

[0088] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure of formula Ib:

[0089]

[0090] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of Formula Ib, wherein R 5 , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;SPh;OPh;CMe 2 Ph; N(Ph) 2 ; carbazolyl; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0091] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R 5 , R XIII , R XIV and / or R XV To form an aromatic ring or a heteroaromatic ring;

[0092] Among them, the adjacent groups R 5 , R XIII , R XIV and / or R XV They may optionally be combined with each other to form an aromatic ring.

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

[0094]

[0095] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ib or Formula Ib-1a, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;OPh;CMe 2 Ph; N(Ph) 2 ; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0096] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R V To R XII To form an aromatic ring or a heteroaromatic ring.

[0097] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ib-1a-1 to Formula Ib-1a-19, or consists of a structure selected from the group consisting of Formula Ib-1a-1 to Formula Ib-1a-19:

[0098]

[0099] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ib or Formula Ib-1a, wherein R V and R XII Not all represent hydrogen.

[0100] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ib or Formula Ib-1a, wherein R V and R XII Unlike hydrogen.

[0101] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ib or Formula Ib-1a, wherein R V =R XII and / or R X =R VII .

[0102] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ib or Formula Ib-1a, wherein R V =R XII And R X =R VII .

[0103] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of a structure of Formula Ib or Formula Ib-1a, wherein R 1 , R 2 , R 3 and R 4 is independently selected at each occurrence from the group consisting of: hydrogen; C 1 -C 5 Alkyl, optionally substituted with one or more substituents R 5 ; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0104] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ib-1b:

[0105]

[0106] In yet another embodiment of the invention, R 5 , R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV and R XVindependently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; triazine group, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0107] In yet another embodiment of the invention, R 5 , R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3and Ph; pyrimidinyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; and a triazine group, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph.

[0108] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ib-1c:

[0109]

[0110] In one embodiment of the invention, the organic molecule comprises or consists of the structure of formula Ib-2a:

[0111]

[0112] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ib-2a1, Formula Ib-2a2, and Formula Ib-2a3, or consists of a structure selected from the group consisting of Formula Ib-2a1, Formula Ib-2a2, and Formula Ib-2a3:

[0113]

[0114] Therein, the above definitions apply.

[0115] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ib-2a4, Formula Ib-2a5, and Formula Ib-2a6, or consists of a structure selected from the group consisting of Formula Ib-2a4, Formula Ib-2a5, and Formula Ib-2a6:

[0116]

[0117] Therein, the above definitions apply.

[0118] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ib-2a7, Formula Ib-2a8, and Formula Ib-2a9, or consists of a structure selected from the group consisting of Formula Ib-2a7, Formula Ib-2a8, and Formula Ib-2a9:

[0119]

[0120] Therein, the above definitions apply.

[0121] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ib-2b:

[0122]

[0123] In one embodiment of the invention, the organic molecule comprises or consists of the structure of Formula Ib-2c:

[0124]

[0125] In a preferred embodiment of the invention, the organic molecule according to the invention comprises a structure of formula Ib-2a, formula Ib-2b or formula Ib-2c, or is composed of a structure of formula Ib-2a, formula Ib-2b or formula Ib-2c, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;OPh;CMe 2 Ph; N(Ph) 2 ; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0126] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R V To R XII To form an aromatic ring or a heteroaromatic ring.

[0127] In a preferred embodiment of the invention, the organic molecule according to the invention comprises a structure of formula Ib-2a, formula Ib-2b or formula Ib-2c, or is composed of a structure of formula Ib-2a, formula Ib-2b or formula Ib-2c, wherein R V and R XII Not all represent hydrogen.

[0128] In certain embodiments of the invention, the organic molecule according to the invention comprises a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, or is composed of a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, wherein R V and R XII Unlike hydrogen.

[0129] In another embodiment of the invention, the organic molecule according to the invention comprises a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, or is composed of a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, wherein R V =R XII and / or R X =R VII .

[0130] In certain embodiments of the invention, the organic molecule according to the invention comprises a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, or is composed of a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, wherein R V =R XII And R X =R VII .

[0131] In another embodiment of the invention, the organic molecule according to the invention comprises a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, or is composed of a structure of Formula Ib-2a, Formula Ib-2b or Formula Ib-2c, wherein R 1 , R 2 , R 3 and R 4 is independently selected at each occurrence from the group consisting of: hydrogen; C 1 -C 5 Alkyl, optionally substituted with one or more substituents R 5 ; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0132] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of Formula Ib-2a, Formula Ib-2b, or Formula Ib-2c, wherein R 5 , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; deuterium; halogen; Me;i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;SPh;OPh;CMe 2 Ph; N(Ph) 2 ; carbazolyl; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0133] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R 5 , R XIII , R XIV and / or R XV To form an aromatic ring or a heteroaromatic ring;

[0134] Among them, the adjacent groups R 5 , R XIII , R XIV and / or R XV They may optionally be combined with each other to form an aromatic ring.

[0135] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of formula Ib-3:

[0136]

[0137] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of the structure of formula Ib-3, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;OPh;CMe 2 Ph; N(Ph) 2 ; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF3 and Ph; one or more substituents from the group consisting of;

[0138] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R V To R XII To form an aromatic ring or a heteroaromatic ring.

[0139] In a preferred embodiment of the invention, the organic molecule according to the invention comprises or consists of the structure of formula Ib-3, wherein R V and R XII Not all represent hydrogen.

[0140] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of formula Ib-3, wherein R V and R XII Unlike hydrogen.

[0141] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of the structure of formula Ib-3, wherein R V =R XII and / or R X =R VII .

[0142] In certain embodiments of the invention, the organic molecule according to the invention comprises or consists of a structure of formula Ib-3, wherein R V =R XII And R X =R VII .

[0143] In another embodiment of the invention, the organic molecule according to the invention comprises or consists of the structure of formula Ib-3, wherein R 1 , R 2 , R 3 and R 4 is independently selected at each occurrence from the group consisting of: hydrogen; C 1 -C 5 Alkyl, optionally substituted with one or more substituents R 5 ; C 6 -C 60 Aryl, optionally substituted with one or more substituents R 5 ; and C 3 -C 57 Heteroaryl, optionally substituted with one or more substituents R 5 .

[0144] In certain embodiments of the invention, the organic molecule comprises or consists of a structure of Formula Ib-3, wherein R 5 , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; deuterium; halogen; Me; i Pr; t Bu; CN; CF 3 ;SiMe 3 ;SiPh 3 ;SPh;OPh;CMe 2 Ph; N(Ph) 2 ; carbazolyl; and Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; one or more substituents from the group consisting of;

[0145] Among them, N(Ph) 2 , OPh and CMe 2 The Ph in Ph is optionally bonded to an adjacent group R 5 , R XIII , R XIV and / or R XV To form an aromatic ring or a heteroaromatic ring;

[0146] Among them, the adjacent groups R 5 , R XIII , R XIV and / or R XV They may optionally be combined with each other to form an aromatic ring.

[0147] In certain embodiments of the invention, the organic molecule comprises a structure selected from the group consisting of Formula Ib-31, Formula Ib-32, and Formula Ib-33, or consists of a structure selected from the group consisting of Formula Ib-31, Formula Ib-32, and Formula Ib-33:

[0148]

[0149] Therein, the above definitions apply.

[0150] In certain embodiments of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula Ib-34, Formula Ib-35, and Formula Ib-36:

[0151]

[0152] Therein, the above definitions apply.

[0153] In certain embodiments of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula Ib-37, Formula Ib-38, and Formula Ib-39:

[0154]

[0155] Therein, the above definitions apply.

[0156] In yet another embodiment of the invention, R 5 , R I , R II , R III , R IV , R V , R VI , R VII , R IX , R X , R XI , R XII , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; triazine group, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .

[0157] In yet another embodiment of the invention, R 5 , R I , R II , R III , RIV , R V , R VI , R VII , R IX , R X , R XI , R XII , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF 3 ; Ph, optionally substituted with independently selected from Me, i Pr, t Bu, CN, CF 3 and Ph; pyridyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph; and a triazine group, optionally substituted with a substituent selected independently from Me, i Pr, t Bu, CN, CF 3 and Ph. BRIEF DESCRIPTION OF THE DRAWINGS

[0158] Figure 1 is the emission spectrum of Example 1 (10 wt. % in PMMA). DETAILED DESCRIPTION

[0159] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense as any monocyclic, bicyclic or polycyclic aromatic moiety. Therefore, aryl contains 6 to 60 aromatic ring atoms, and heteroaryl contains 5 to 60 aromatic ring atoms of which at least one is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms can be given as a subscript number in the definition of certain substituents. Specifically, the heteroaromatic ring includes one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense as any monocyclic, bicyclic or polycyclic heteroaromatic moiety including at least one heteroatom. The heteroatom can be the same or different at each occurrence, and can be individually selected from the group consisting of N, O and S. Therefore, the term "arylene" refers to a divalent substituent having two binding points with other molecular structures and therefore used as a connecting base structure. In the case where the group in the exemplary embodiment is defined as different from the definition given here (for example, the number of aromatic ring atoms or the number of heteroatoms are different from the given definition), the definition in the exemplary embodiment will be applied. According to the invention, the condensed (cyclized) aromatic polycyclic or heteroaromatic polycyclic ring is composed of two or more monoaromatic or heteroaromatic rings that form a polycyclic ring via a condensation reaction.

[0160] Specifically, as used throughout this application, the term aryl or heteroaryl includes groups that can be bonded via any position of an aromatic group or a heteroaromatic group, the group being derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, Perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, 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, naphthymidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzo Oxazole, naphthoxazole, anthraxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthyridine, carboline, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,2,3,4-tetrazine, purine, pteridine, indolizine and benzothiadiazole or a combination of the foregoing groups.

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

[0162] As used throughout, the term "biphenyl" as a substituent may be understood in the broadest sense as ortho-biphenyl, meta-biphenyl or para-biphenyl, wherein ortho, meta and para are defined with respect to the binding position to another chemical moiety.

[0163] As used above and herein, the term alkyl may be understood in the broadest sense as any linear, branched or cyclic alkyl substituent. Specifically, the term alkyl includes such substituents as methyl (Me), ethyl (Et), n-propyl ( n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl ( s Bu), tert-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, sec-hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1- Bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hexan-1-yl, 1,1-dimethyl-n-heptan-1-yl, 1,1-dimethyl-n-octan-1-yl, 1,1-dimethyl-n-decan-1-yl, 1,1-dimethyl-n-dodecan-1-yl, 1,1-dimethyl-n-tetradecan-1-yl, 1,1-dimethyl-n-hexadecan-1-yl, 1,1-dimethyl-n-octadecan-1-yl, 1,1-diethyl-n-hexan-1-yl, 1,1-diethyl-n-heptan-1-yl, 1,1-diethyl-n-octan-1-yl, 1,1-diethyl-n-decan-1-yl, 1,1-diethyl-n- dodecan-1-yl, 1,1-diethyl-n-tetradecane-1-yl, 1,1-diethyl-n-hexadecane-1-yl, 1,1-diethyl-n-octadecane-1-yl, 1-(n-propyl)-cyclohexan-1-yl, 1-(n-butyl)-cyclohexan-1-yl, 1-(n-hexyl)-cyclohexan-1-yl, 1-(n-octyl)-cyclohexan-1-yl and 1-(n-decyl)-cyclohexan-1-yl.

[0164] As above and used in this, the term alkenyl includes straight chain, branched and cyclic alkenyl substituents. The term alkenyl illustratively includes such substituents: vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0165] As used above and herein, the term alkynyl includes straight chain, branched and cyclic alkynyl substituents. The term alkynyl illustratively includes ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0166] As used above and herein, the term alkoxy includes linear, branched and cyclic alkoxy substituents. The term alkoxy illustratively includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy and 2-methylbutoxy.

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

[0168] As used above and herein, 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 herein, hydrogen (H) may also be replaced by deuterium at each occurrence.

[0170] It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written as if it is a fragment (e.g., naphthyl, dibenzofuranyl) or as if it is the entire molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0171] In one embodiment, the organic molecules according to the invention have an excited state lifetime of no more than 25 μs, no more than 15 μs, specifically no more than 10 μs, more preferably no more than 8 μs or no more than 6 μs and even more preferably no more than 4 μs in a film of poly(methyl methacrylate) (PMMA) having 10 wt % of organic molecules at room temperature.

[0172] In one embodiment of the invention, the organic molecule according to the invention represents a thermally activated delayed fluorescence (TADF) emitter that exhibits a wavelength of less than 5000 cm -1 (Preferably less than 3000cm -1 , more preferably less than 1500cm -1 , even more preferably less than 1000 cm -1 Or even less than 500cm -1 ) corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1) ΔE ST value.

[0173] In yet another embodiment of the invention, the organic molecule according to the invention has an emission peak in the visible light or closest ultraviolet light range (i.e., in the wavelength range of 480 nm to 580 nm) at room temperature and a half-maximum full width of less than 0.50 eV (preferably less than 0.48 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV or even less than 0.40 eV) in a film of poly(methyl methacrylate) (PMMA) having 10 wt % of the organic molecule.

[0174] In yet another embodiment of the invention, the organic molecules according to the invention have an emission peak in the visible light or closest ultraviolet light range (i.e., in the wavelength range of 480 nm to 580 nm) and a half-maximum full width of less than 0.40 eV in a film of poly(methyl methacrylate) (PMMA) having 10 wt % of the organic molecules at room temperature.

[0175] Orbital and excited state energies can be determined experimentally or by calculations using quantum chemical methods (specifically, density functional theory calculations). The energy of the highest occupied molecular orbital (E HOMO ) is determined by methods known to those skilled in the art via cyclic voltammetry measurements with an accuracy of 0.1 eV. The lowest unoccupied molecular orbital energy (E LUMO ) was determined as the onset of the absorption spectrum.

[0176] The starting point of the absorption spectrum is determined by calculating the intersection of the tangent line of the absorption spectrum with the x-axis. The tangent line of the absorption spectrum is set at the low energy side of the absorption band and at the point of half maximum of the maximum intensity of the absorption spectrum.

[0177] The energy of the first excited triplet state (T1) is determined by the onset of the emission spectrum at low temperature (usually, at 77K). For host compounds in which the first excited singlet state and the lowest triplet state differ in energy by >0.4 eV, phosphorescence is usually visible in the steady-state spectrum in 2-Me-THF. Therefore, the triplet energy can be determined as the onset of the phosphorescence spectrum. For TADF emitter molecules, if not otherwise specified, the energy of the first excited triplet state (T1) is determined by the onset of the delayed emission spectrum at 77K, which is measured in a film of PMMA with 10 wt% of the emitter. For both host and emitter compounds, if not otherwise specified, the energy of the first excited singlet state S1 is determined by the onset of the emission spectrum at room temperature, which is measured in a film of PMMA with 10 wt% of the host or emitter compound.

[0178] The starting point of the emission spectrum is determined by calculating the intersection of the tangent line of the emission spectrum with the x-axis. The tangent line of the emission spectrum is set at the high energy side of the emission band and at the point of half maximum of the maximum intensity of the emission spectrum.

[0179] A further aspect of the invention relates to the use of the organic molecules according to the invention as luminescent emitter or as absorber and / or as host material and / or as electron transport material and / or as hole injection material and / or as hole blocking material in optoelectronic devices.

[0180] Optoelectronic devices can be understood in the broadest sense as any device based on organic materials suitable for emitting light in the visible or closest ultraviolet (UV) range (i.e., in the range of wavelengths from 380nm to 800nm). More preferably, the optoelectronic device can be capable of emitting light in the visible range (i.e., 400nm to 800nm).

[0181] In the context of this application, the optoelectronic device is more particularly selected from the group consisting of:

[0182] Organic light-emitting diodes (OLEDs);

[0183] ·Light-emitting electrochemical cells;

[0184] OLED sensors, in particular, gas sensors and vapor sensors that are not hermetically isolated from the outside;

[0185] Organic diodes;

[0186] Organic solar cells;

[0187] Organic transistors;

[0188] Organic field effect transistors;

[0189] Organic lasers; and

[0190] Down-conversion components.

[0191] The light-emitting electrochemical cell comprises three layers (ie cathode, anode and active layer) which contain the organic molecules according to the invention.

[0192] In a preferred embodiment in the context of this application, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic laser and a light emitting transistor.

[0193] In one embodiment, the light emitting layer (or "emitting layer") of an organic light emitting diode includes the organic molecules according to the invention.

[0194] In one embodiment, the light-emitting layer of an organic light-emitting diode includes not only the organic molecule according to the invention, but also a host material whose triplet (T1) energy level and singlet (S1) energy level are energetically higher than those of the organic molecule.

[0195] Another aspect of the invention relates to a composition comprising or consisting of the following ingredients:

[0196] (a) the inventive organic molecules, in particular in the form of emitters and / or hosts; and

[0197] (b) one or more emitter and / or host materials different from the inventive organic molecules; and

[0198] (c) optionally, one or more dyes and / or one or more solvents.

[0199] In yet another embodiment of the invention, the composition has a photoluminescence quantum yield (PLQY) greater than 10%, preferably greater than 20%, more preferably greater than 40%, even more preferably greater than 60% or even greater than 70% at room temperature.

[0200] Composition with at least one other emitter

[0201] One embodiment of the invention relates to a composition comprising or consisting of the following ingredients:

[0202] (i) 1 to 50 wt% (preferably, 5 to 40 wt%, specifically, 10 to 30 wt%) of an organic molecule (E) according to the invention;

[0203] (ii) 5 to 98 wt % (preferably, 30 to 93.9 wt %, specifically, 40 to 88 wt %) of a host compound (H);

[0204] (iii) 1 to 30% by weight (in particular 1 to 20% by weight, preferably 1 to 5% by weight) of at least one further emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention; and

[0205] (iv) optionally, 0 to 94 wt% (preferably, 0.1 to 65 wt%, specifically, 1 to 50 wt%) of at least one other host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0206] (v) Optionally, 0 wt % to 94 wt % (preferably, 0 wt % to 65 wt %, specifically, 0 wt % to 50 wt %) of a solvent.

[0207] The ingredients or components are selected so that the sum of the weights of the ingredients add up to 100%.

[0208] In yet another embodiment of the invention, the composition has an emission peak in the visible light or closest ultraviolet light range (ie, in the range of wavelengths from 380 nm to 800 nm).

[0209] In one embodiment of the invention, the at least one further emitter molecule (F) is a purely organic emitter.

[0210] In one embodiment of the invention, at least one further emitter molecule (F) is a pure organic TADF emitter. Pure organic TADF emitters are known from the prior art, for example, Wong and Zysman-Colman ("Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light-Emitting Diodes", Adv. Mater. 2017 Jun; 29 (22)).

[0211] In one embodiment of the invention, the at least one further emitter molecule (F) is a fluorescent emitter (particularly a red, yellow or green fluorescent emitter).

[0212] In a further embodiment of the invention, the composition comprising at least one further emitter molecule (F) exhibits an emission peak in the visible or closest ultraviolet range (i.e. in the range of wavelengths from 380 nm to 800 nm) at room temperature and a full width at half maximum of less than 0.30 eV (particularly less than 0.25 eV, preferably less than 0.22 eV, more preferably less than 0.19 eV or even less than 0.17 eV) and a lower limit of 0.05 eV.

[0213] Compositions wherein at least one further emitter molecule (F) is a green fluorescent emitter

[0214] In yet another embodiment of the invention, the at least one further emitter molecule (F) is a fluorescent emitter (particularly a green fluorescent emitter).

[0215] In one embodiment, at least one further emitter molecule (F) is a fluorescent emitter selected from the group consisting of:

[0216]

[0217]

[0218] In yet another embodiment of the invention, the composition has an emission peak in the visible light or closest ultraviolet light range, i.e., in the range of wavelengths from 380 nm to 800 nm (specifically between 485 nm and 590 nm, preferably between 505 nm and 565 nm, even more preferably between 515 nm and 545 nm).

[0219] Compositions wherein at least one further emitter molecule (F) is a red fluorescent emitter

[0220] In yet another embodiment of the invention, the at least one further emitter molecule (F) is a fluorescent emitter (particularly a red fluorescent emitter).

[0221] In one embodiment, at least one further emitter molecule (F) is a fluorescent emitter selected from the group consisting of:

[0222]

[0223]

[0224]

[0225] In yet another embodiment of the invention, the composition has an emission peak in the visible light or closest ultraviolet light range, i.e., in the range of wavelengths from 380 nm to 800 nm (specifically between 590 nm and 690 nm, preferably between 610 nm and 665 nm, even more preferably between 620 nm and 640 nm).

[0226] EML

[0227] In one embodiment, the light emitting layer (EML) of the organic light emitting diode of the invention comprises (or consists essentially of) a composition comprising or consisting of the following components:

[0228] (i) 1 to 50 wt% (preferably, 5 to 40 wt%, specifically, 10 to 30 wt%) of one or more organic molecules (E) according to the invention;

[0229] (ii) 5 to 99 wt% (preferably, 30 to 94.9 wt%, specifically, 40 to 89 wt%) of at least one host compound (H); and

[0230] (iii) optionally, 0 to 94 wt% (preferably, 0.1 to 65 wt%, specifically, 1 to 50 wt%) of at least one other host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0231] (iv) optionally, 0 wt % to 94 wt % (preferably, 0 wt % to 65 wt %, specifically, 0 wt % to 50 wt %) of a solvent; and

[0232] (v) optionally, 0 to 30% by weight (in particular 0 to 20% by weight, preferably 0 to 5% by weight) of at least one further emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention.

[0233] Preferably, energy can be transferred from the main compound (H) to one or more of the organic molecules (E) of the invention, specifically, energy can be transferred from the first excited triplet state (T1(H)) of the main compound (H) to the first excited triplet state (T1(E)) of one or more of the organic molecules (E) according to the invention, and / or from the first excited singlet state (S1(H)) of the main compound (H) to the first excited singlet state (S1(E)) of one or more of the organic molecules (E) according to the invention.

[0234] In one embodiment, the host compound (H) has an energy (E) in the range of -5 eV to -6.5 eV. HOMO (H)), an organic molecule (E) according to the invention has an energy (E HOMO (E)) is the highest occupied molecular orbital (HOMO(E)), where E HOMO (H)>E HOMO (E).

[0235] In another embodiment, the host compound (H) has an energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), according to the invention, an organic molecule (E) has an energy (E LUMO (E)) is the lowest unoccupied molecular orbital (LUMO(E)), where E LUMO (H)>E LUMO (E).

[0236] An emitting layer (EML) comprising at least one other host compound (D)

[0237] In yet another embodiment, the light emitting layer (EML) of the organic light emitting diode of the invention comprises (or consists essentially of) a composition comprising or consisting of the following components:

[0238] (i) 1 to 50 wt. % (preferably 5 to 40 wt. %, in particular 10 to 30 wt. %) of one organic molecule (E) according to the invention;

[0239] (ii) 5 to 99 wt % (preferably, 30 to 94.9 wt %, specifically, 40 to 89 wt %) of a host compound (H); and

[0240] (iii) 0 to 94 wt% (preferably, 0.1 to 65 wt%, specifically, 1 to 50 wt%) of at least one other host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0241] (iv) optionally, 0 wt % to 94 wt % (preferably, 0 wt % to 65 wt %, specifically, 0 wt % to 50 wt %) of a solvent; and

[0242] (v) optionally, 0 to 30% by weight (in particular 0 to 20% by weight, preferably 0 to 5% by weight) of at least one further emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention.

[0243] In one embodiment of the organic light emitting diode of the invention, the host compound (H) has an energy (E HOMO (H)), at least one of the other host compounds (D) has an energy (E HOMO (D)) of the highest occupied molecular orbital (HOMO(D)), where E HOMO (H)>E HOMO (D). Relationship E HOMO (H)>E HOMO (D) It is conducive to efficient hole transport.

[0244] In another embodiment, the host compound (H) has an energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), at least one other host compound (D) has an energy (E LUMO (D)) of the lowest unoccupied molecular orbital (LUMO(D)), where E LUMO (H)>ELUMO (D). Relationship E LUMO (H)>E LUMO (D) Facilitates efficient electron transport.

[0245] In one embodiment of the organic light emitting diode of the invention, the host compound (H) has an energy (E HOMO (H))'s highest occupied molecular orbital (HOMO(H)) and its energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), and

[0246] At least one other host compound (D) has an energy (E HOMO (D)) and the highest occupied molecular orbital (HOMO(D)) and the energy (E LUMO (D))'s lowest unoccupied molecular orbital (LUMO(D)),

[0247] The invented organic molecule (E) has energy (E HOMO (E))'s highest occupied molecular orbital (HOMO(E)) and its energy (E LUMO (E))'s lowest unoccupied molecular orbital (LUMO(E)),

[0248] in,

[0249] E HOMO (H)>E HOMO (D), and according to the energy level (E) of the highest occupied molecular orbital (HOMO (E)) of the organic molecule (E) of the invention HOMO (E)) and the energy level (E) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) HOMO (H)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0250] E LUMO (H)>E LUMO (D), and according to the energy level (E) of the lowest unoccupied molecular orbital (LUMO (E)) of the organic molecule (E) of the invention LUMO (E)) and the energy level (E) of the lowest unoccupied molecular orbital (LUMO (D)) of at least one other host compound (D) LUMO (D)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0251] a light-emitting layer (EML) comprising at least one further emitter molecule (F)

[0252] In yet another embodiment, the light emitting layer (EML) comprises (or consists (essentially) of) a composition comprising or consisting of:

[0253] (i) 1 to 50 wt. % (preferably 5 to 40 wt. %, in particular 10 to 30 wt. %) of one organic molecule (E) according to the invention;

[0254] (ii) 5 to 98 wt % (preferably, 30 to 93.9 wt %, specifically, 40 to 88 wt %) of a host compound (H);

[0255] (iii) 1 to 30% by weight (in particular 1 to 20% by weight, preferably 1 to 5% by weight) of at least one further emitter molecule (F) having a structure different from that of the organic molecule (E) according to the invention; and

[0256] (iv) optionally, 0 to 94 wt% (preferably, 0.1 to 65 wt%, specifically, 1 to 50 wt%) of at least one other host compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0257] (v) Optionally, 0 wt % to 94 wt % (preferably, 0 wt % to 65 wt %, specifically, 0 wt % to 50 wt %) of a solvent.

[0258] In yet another embodiment, the light emitting layer (EML) comprises (or (essentially consists of) a composition as described in the composition with at least one further emitter and at least one further emitter molecule (F) as defined in the composition wherein the at least one further emitter molecule (F) is a green fluorescent emitter.

[0259] In yet another embodiment, the light emitting layer (EML) comprises (or (essentially consists of) a composition as described in the composition with at least one further emitter and at least one further emitter molecule (F) as defined in the composition wherein the at least one further emitter molecule (F) is a red fluorescent emitter.

[0260] In one embodiment of the light-emitting layer (EML) comprising at least one further emitter molecule (F), energy can be transferred from one or more inventive organic molecules (E) to at least one further emitter molecule (F), specifically, energy can be transferred from a first excited singlet state (S1(E)) of one or more inventive organic molecules (E) to a first excited singlet state (S1(F)) of at least one further emitter molecule (F).

[0261] In one embodiment, the first excited singlet state (S1(H)) of a main compound (H) of the light-emitting layer is higher in energy than the first excited singlet state (S1(E)) of one or more inventive organic molecules (E): S1(H)>S1(E), and the first excited singlet state (S1(H)) of a main compound (H) is higher in energy than the first excited singlet state (S1(F)) of at least one emitter molecule (F): S1(H)>S1(F).

[0262] In one embodiment, the first excited triplet state (T1(H)) of one host compound (H) is higher in energy than the first excited triplet state (T1(E)) of one or more inventive organic molecules (E): T1(H)>T1(E), and the first excited triplet state (T1(H)) of one host compound (H) is higher in energy than the first excited triplet state (T1(F)) of at least one emitter molecule (F): T1(H)>T1(F).

[0263] In one embodiment, the first excited singlet state (S1(E)) of the one or more inventive organic molecules (E) is higher in energy than the first excited singlet state (S1(F)) of the at least one emitter molecule (F): S1(E)>S1(F).

[0264] In one embodiment, the first excited triplet state (T1(E)) of the one or more inventive organic molecules (E) is higher in energy than the first excited singlet state (T1(F)) of the at least one emitter molecule (F): T1(E)>T1(F).

[0265] In one embodiment, the first excited triplet state (T1(E)) of one or more inventive organic molecules (E) is higher in energy than the first excited singlet state (T1(F)) of at least one emitter molecule (F): T1(E)>T1(F), wherein the absolute value of the energy difference between T1(E) and T1(F) is greater than 0.3 eV (preferably greater than 0.4 eV or even greater than 0.5 eV).

[0266] In one embodiment, the host compound (H) has an energy (E HOMO (H))'s highest occupied molecular orbital (HOMO(H)) and its energy (E LUMO (H)) of the lowest unoccupied molecular orbital (LUMO(H)), and

[0267] An organic molecule (E) according to the invention has an energy (E HOMO (E))'s highest occupied molecular orbital (HOMO(E)) and its energy (E LUMO (E))'s lowest unoccupied molecular orbital (LUMO(E)),

[0268] At least one other emitter molecule (F) has an energy (E HOMO (F)) and the highest occupied molecular orbital (HOMO(F)) and the energy (E LUMO (F))'s lowest unoccupied molecular orbital (LUMO(F)),

[0269] in,

[0270] E HOMO (H)>E HOMO (E), the energy level (E) of the highest occupied molecular orbital (HOMO(F)) of at least one other emitter molecule (F) HOMO (F)) and the energy level (E) of the highest occupied molecular orbital (HOMO(H)) of the host compound (H) HOMO (H)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0271] E LUMO (H)>E LUMO (E), the energy level (E) of the lowest unoccupied molecular orbital (LUMO(F)) of at least one other emitter molecule (F) LUMO (F)) and the energy level (E) of the lowest unoccupied molecular orbital (LUMO (E)) of an organic molecule (E) according to the invention LUMO(E)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0272] Optoelectronic devices

[0273] In yet another aspect, the invention relates to an optoelectronic device comprising an organic molecule or composition as described herein, more particularly, the optoelectronic device is in the form of a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell, an OLED sensor (particularly, a gas sensor and a vapor sensor that are not externally sealed and isolated), an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser and a down-conversion element.

[0274] In a preferred embodiment, the optoelectronic device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC) and a light emitting transistor.

[0275] In one embodiment of the inventive optoelectronic device, the organic molecules according to the invention are used as emitting material in the light emitting layer (EML).

[0276] In one embodiment of the inventive optoelectronic device, the light emitting layer (EML) consists of the composition according to the invention as described herein.

[0277] When the optoelectronic device is an OLED, it may, for example, exhibit the following layer structure:

[0278] 1. Base

[0279] 2. Anode layer, A

[0280] 3. Hole injection layer, HIL

[0281] 4. Hole transport layer, HTL

[0282] 5. Electron blocking layer, EBL

[0283] 6. Emission layer, EML

[0284] 7. Hole blocking layer, HBL

[0285] 8. Electron Transport Layer, ETL

[0286] 9. Electron injection layer, EIL

[0287] 10. Cathode layer, C,

[0288] Where the OLED comprises each layer, only optionally different layers may be combined, the OLED may comprise more than one layer of each layer type defined above.

[0289] Additionally, optoelectronic devices may optionally include one or more protective layers that protect the device from damage due to exposure to harmful substances in the environment, including, for example, moisture, steam, and / or gases.

[0290] In one embodiment of the invention, the optoelectronic device is an OLED exhibiting the following inverted layer structure:

[0291] 1. Base

[0292] 2. Cathode layer, C

[0293] 3. Electron injection layer, EIL

[0294] 4. Electron Transport Layer, ETL

[0295] 5. Hole blocking layer, HBL

[0296] 6. Emission layer, EML

[0297] 7. Electron blocking layer, EBL

[0298] 8. Hole transport layer, HTL

[0299] 9. Hole injection layer, HIL

[0300] 10. Anode layer, A,

[0301] Wherein an OLED with an inverted layer structure comprises each layer, only optionally different layers may be combined, the OLED may comprise more than one layer of each layer type defined above.

[0302] In one embodiment of the invention, the optoelectronic device is an OLED that can exhibit a stacked architecture. In this architecture, the individual units are stacked on top of each other, as opposed to the typical arrangement in which OLEDs are placed side by side. Mixed light can be produced with an OLED that exhibits a stacked architecture, specifically, white light can be produced by stacking a blue OLED, a green OLED, and a red OLED. In addition, an OLED that exhibits a stacked architecture can optionally include a charge generation layer (CGL), which is typically positioned between two OLED subunits and is typically composed of an n-doped layer and a p-doped layer, and the n-doped layer of one CGL is typically positioned close to the anode layer.

[0303] In one embodiment of the invention, the optoelectronic device is an OLED comprising two or more emission layers between an anode and a cathode. Specifically, this so-called tandem OLED comprises three emission layers, wherein one emission layer emits red light, one emission layer emits green light, and one emission layer emits blue light, and optionally further comprises layers such as charge generation layers, blocking layers or transport layers between the respective emission layers. In another embodiment, the emission layers are stacked adjacently. In another embodiment, the tandem OLED comprises a charge generation layer between every two emission layers. In addition, adjacent emission layers or emission layers separated by charge generation layers may be merged.

[0304] The substrate can be formed by any material or a combination of materials. Most commonly, a glass slide is used as a substrate. Alternatively, a thin metal layer (e.g., copper, gold, silver or aluminum film) or a plastic film or a glass slide can be used. This can allow a higher degree of flexibility. The anode layer (A) is mainly composed of a material that allows a (substantially) transparent film to be obtained. Since at least one of the two electrodes should be (substantially) transparent to allow light to be emitted from the OLED, the anode layer (A) or the cathode layer (C) is transparent. Preferably, the anode layer (A) includes a large amount of transparent conductive oxide (TCO), or even consists of a transparent conductive oxide (TCO). Such anode layer (A) can exemplarily include 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.

[0305] Preferably, the anode layer (A) consists (essentially) of 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 by using a hole injection layer (HIL). In addition, since the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is promoted, the HIL can promote the injection of quasi-charge carriers (i.e., holes). The hole injection layer (HIL) can include poly (3,4-ethylenedioxythiophene) (PEDOT), polystyrene sulfonate (PSS), MoO 2 、V 2 O 5, CuPC or CuI (specifically, a mixture of PEDOT and PSS). The hole injection layer (HIL) may also prevent the diffusion of metal from the anode layer (A) into the hole transport layer (HTL). The HIL may illustratively include 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'-bis(1- =The following are the amino acids: N,N'-diphenyl-N,N'-bis-[4-(N,N-diphenyl-amino)phenyl]benzidine, MeO-TPD (N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine), HAT-CN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine).

[0306] Adjacent to the anode layer (A) or the hole injection layer (HIL), a hole transport layer (HTL) is typically positioned. Here, any hole transport compound can be used. Exemplarily, 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 light-emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a fairly high energy level of its triplet state (T1). For example, the hole transport layer (HTL) may include tris(4-carbazol-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), α-NPD (2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine), TAPC (4,4'-cyclohexyl-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]tris(2-naphthyl)amino]tris(2-naphthyl)phenylamine), 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl ... The HTL may include a star-shaped heterocycle of 9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,9'H-3,3'-bicarbazole). In addition, the HTL may include a p-doped layer that may be composed of an inorganic dopant or an organic dopant in an organic hole transport matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide may be used as inorganic dopants, for example. Tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or a transition metal complex may be exemplarily used as the organic dopant.

[0307] The EBL may illustratively include mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazol-9-yl)biphenyl), tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), and / or DCB (N,N′-dicarbazyl-1,4-dimethylbenzene).

[0308] Adjacent to the hole transport layer (HTL), an emission layer (EML) is typically positioned. The emission layer (EML) includes at least one organic molecule. Specifically, the EML includes at least one organic molecule according to the invention. Typically, the EML additionally includes one or more host materials. Exemplarily, the host material is selected from CBP (4,4'-bis(N-carbazolyl)biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), 9-[3-(dibenzofuran)-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2 -yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothienyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(terphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirobifluorene-2-yl)-1,3,5-triazine). The host material should typically be selected to exhibit a first triplet (T1) energy level and a first singlet (S1) energy level that are energetically higher than the first triplet (T1) energy level and the first singlet (S1) energy level of the organic molecule.

[0309] In one embodiment of the invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one luminescent organic molecule according to the invention and a hybrid 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-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole as a hole-dominant host. In another embodiment, the EML includes 50 wt % to 80 wt % (preferably 60 wt % to 75 wt %) of a host, 10 wt % to 45 wt % (preferably 15 wt % to 30 wt %) of T2T, and 5 wt % to 40 wt % (preferably 10 wt % to 30 wt %) of an organic molecule according to the invention, wherein the host is selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole.

[0310] Adjacent to the light-emitting layer (EML), an electron transport layer (ETL) may be positioned. Here, any electron transporter may be used. For example, electron-poor compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). The ETL may include NBphen (2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq 3 (tris(8-hydroxyquinoline)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), 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-triazine)]-1,1'-biphenyl). Optionally, the ETL can be doped with a material such as Liq. The electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0311] HBL may include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline = bathocuproine), BAlq (bis(8-hydroxy-2-methylquinolinol)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq 3 (tris(8-hydroxyquinoline)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(terphenyl-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)benzene / 1,3,5-tris(carbazol-9-yl)benzene).

[0312] The cathode layer (C) may be positioned adjacent to the electron transport layer (ETL). For example, the cathode layer (C) may comprise 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, or may 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 of a (substantially) opaque metal such as Mg, Ca, or Al. Alternatively or additionally, the cathode layer (C) may also comprise graphite and / or carbon nanotubes (CNTs). Optionally, the cathode layer (C) may also consist of nanoscale silver wires.

[0313] The OLED may further optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (8-hydroxyquinoline lithium), Li 2 O.BaF 2 , MgO and / or NaF.

[0314] Alternatively, the electron transport layer (ETL) and / or the hole blocking layer (HBL) may include one or more host compounds.

[0315] In order to further modify the emission spectrum and / or absorption spectrum of the light-emitting layer (EML), the light-emitting layer (EML) may further include one or more other emitter molecules (F). Such an emitter molecule (F) may be any emitter molecule known in the art. Preferably, this emitter molecule (F) is a molecule having a structure different from that of the organic molecule (E) according to the invention. The emitter molecule (F) may optionally be a TADF emitter. Alternatively, the emitter molecule (F) may optionally be a fluorescent and / or phosphorescent emitter molecule capable of shifting the emission spectrum and / or absorption spectrum of the light-emitting layer (EML). For example, by emitting light that is typically red-shifted compared to the light emitted by the organic molecule (E), triplet and / or singlet excitons may be transferred from the organic molecule (E) according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Optionally, the emitter molecule (F) may also cause a two-photon effect (i.e., absorption of half the energy of the absorption maximum by two photons).

[0316] Optionally, the optoelectronic device (e.g., OLED) can be, for example, a substantially white optoelectronic device. Exemplarily, such a white optoelectronic device can include at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Then, there can also be energy transferability (energy transmittance) between the two or more molecules as described above.

[0317] As used herein, if not more specifically defined in a particular context, the color of emitted and / or absorbed light is designated as follows:

[0318] Purple: >380nm to 420nm wavelength range;

[0319] Dark blue: >420nm to 480nm wavelength range;

[0320] Sky blue: >480nm to 500nm wavelength range;

[0321] Green: >500nm to 560nm wavelength range;

[0322] Yellow: >560nm to 580nm wavelength range;

[0323] Orange: >580nm to 620nm wavelength range;

[0324] Red: >620nm to 800nm ​​wavelength range.

[0325] For emitter molecules, this color refers to the emission maximum. Thus, exemplarily, a deep blue emitter has an emission maximum in the range of >420nm to 480nm, a sky blue emitter has an emission maximum in the range of >480nm to 500nm, a green emitter has an emission maximum in the range of >500nm to 560nm, and a red emitter has an emission maximum in the range of >620nm to 800nm.

[0326] Yet another embodiment of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates (CIEx=0.170, CIEy=0.797) (the CIEx and CIEy color coordinates (CIEx=0.170, CIEy=0.797) are close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of the primary color green as defined by ITU-R Recommendation BT.2020 (Rec.2020)), and is therefore suitable for application in ultra-high-definition (UHD) displays (e.g., UHD-TV). In this context, the term "close to" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting (top electrode is transparent) devices are typically used, while the test devices used throughout this application represent bottom-emitting devices (bottom electrode and substrate are transparent). Therefore, a further aspect of the invention relates to an OLED, the emission of which exhibits a CIEx color coordinate of between 0.15 and 0.45 (preferably between 0.15 and 0.35, more preferably between 0.15 and 0.30, or even more preferably between 0.15 and 0.25, or even between 0.15 and 0.20) and / or a CIEy color coordinate of between 0.60 and 0.92 (preferably between 0.65 and 0.90, more preferably between 0.70 and 0.88, or even more preferably between 0.75 and 0.86, or even between 0.79 and 0.84).

[0327] Yet another aspect of the present invention relates to an OLED that emits light having CIEx and CIEy color coordinates (CIEx=0.708, CIEy=0.292) (the CIEx and CIEy color coordinates (CIEx=0.708, CIEy=0.292) are close to the CIEx (=0.708) and CIEy (=0.292) color coordinates of the primary color red as defined by ITU-R Recommendation BT.2020 (Rec.2020)), and is therefore suitable for use in ultra-high-definition (UHD) displays (e.g., UHD-TV). In this context, the term "close to" refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting (top electrode is transparent) devices are typically used, while the test devices used throughout this application represent bottom-emitting devices (bottom electrode and substrate are transparent). Therefore, a further aspect of the invention relates to an OLED, the emission of which exhibits a CIEx color coordinate of between 0.60 and 0.88 (preferably between 0.61 and 0.83, more preferably between 0.63 and 0.78, or even more preferably between 0.66 and 0.76, or even between 0.68 and 0.73) and / or a CIEy color coordinate of between 0.25 and 0.70 (preferably between 0.26 and 0.55, more preferably between 0.27 and 0.45, or even more preferably between 0.28 and 0.40, or even between 0.29 and 0.35).

[0328] Therefore, another aspect of the present invention relates to an OLED having a brightness of 14500 cd / m 2 The invention further comprises a light emitting diode (LED) having an external quantum efficiency of greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 17%, or even greater than 20%) at a wavelength of 495 nm to 580 nm (preferably between 500 nm and 560 nm, more preferably between 510 nm and 550 nm, even more preferably between 510 nm and 540 nm), and / or ... 2 The LT97 value exhibited by the present invention is greater than 100 hours (preferably greater than 250 hours, more preferably greater than 500 hours, even more preferably greater than 750 hours, or even greater than 1000 hours).

[0329] The optoelectronic device (in particular, OLED) according to the present invention can be manufactured by any means of vapor deposition and / or liquid processing. Thus, at least one layer:

[0330] -Prepared by sublimation process,

[0331] -Prepared by organic vapor deposition process,

[0332] -Prepared by gas sublimation process,

[0333] - solution treatment, or

[0334] print.

[0335] The method for manufacturing an optoelectronic device (in particular, an OLED) according to the present invention is known in the art. The different layers are deposited individually and successively on a suitable substrate by means of a subsequent deposition process. The same or different deposition methods may be used to deposit the individual layers.

[0336] Vapor deposition processes illustratively include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as a substrate. Appropriate solvents may be used to process the various layers from a solution or dispersion. Solution deposition processes illustratively include spin coating, dip coating, and jet printing. Liquid processing may optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent may optionally be completely or partially removed by means known in the art.

[0337] Example

[0338] General Synthesis Scheme I

[0339]

[0340] General Synthetic Scheme II

[0341]

[0342] General Synthetic Scheme III

[0343]

[0344] General steps for synthesizing AAV1:

[0345]

[0346] In N 2 Atmosphere, a 2-necked flask equipped with a reflux condenser was charged with E1 (1.0 equivalent), chlorobenzene (100 mL) and subsequently boron tribromide [10294-33-4] (3.5 equivalents). After the mixture was stirred at 100 ° C for 2 hours, the reaction was quenched by adding water (50 mL) at 0 ° C. The precipitate was filtered and dried to obtain the corresponding product P1 as a solid, which was further used without further purification.

[0347] General steps for synthesizing AAV2:

[0348]

[0349] In N 2 Under N atmosphere, a two-necked flask was charged with P1 (1.0 eq.) and chlorobenzene (100 mL) and the mixture was degassed for 10 minutes. Boron trichloride [10294-34-5] (0.5 eq.) was added at 0°C, and the mixture was allowed to warm to room temperature and stirred for 2 hours. 2 Atmosphere, the second two-necked flask was equipped with E2 (3.0 equivalents) and anhydrous tert-butylbenzene (50 mL) and the mixture was degassed for 10 minutes. At 0 ° C, tert-butyl lithium solution [54-19-4] (2.8 equivalents) was added to the second flask, and the reaction mixture was warmed to room temperature and stirred for 30 minutes. After the reaction mixture of the second flask was slowly added to the reaction mixture of the first flask at 0 ° C, the yellow mixture was stirred at room temperature overnight. After evaporating the solvent, the crude mixture was purified by column chromatography (eluent: cyclohexane / dichloromethane) to obtain the corresponding product P2 as a solid.

[0350] Cyclic voltammetry

[0351] The cyclic voltammograms were obtained by mixing the voltammograms with a concentration of 10 -3 The measurement was performed at room temperature in a nitrogen atmosphere using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire), and using FeCp 2 / FeCp 2 + Calibration was performed as an internal standard. HOMO data were corrected for saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0352] Density functional theory calculations

[0353] The molecular structure was optimized using the BP86 functional and the resolution of identity approach (RI). The excitation energies were calculated using the (BP86) optimized structure using the time-dependent DFT (TD-DFT) method. The orbital and excited state energies were calculated using the B3LYP functional. The Def2-SVP basis set and the m4 grid for numerical integration were used. The Turbomole package was used for all calculations.

[0354] Photophysical measurements

[0355] Sample pretreatment: spin coating.

[0356] Instrument: Spin150, SPS euro.

[0357] The sample concentration was 10 mg / mL, dissolved in a suitable solvent.

[0358] Program: 1) 3 sec at 400 U / min. 2) 20 sec at 1000 U / min at 1000 U / min. 3) 10 sec at 4000 U / min at 1000 U / min. After coating, the film was dried at 70° C. for 1 min.

[0359] Photoluminescence spectroscopy and time-correlated single photon counting (TCSPC)

[0360] Steady state emission spectra were measured by a Horiba Scientific, Modell FluoroMax-4 equipped with a 150W xenon arc lamp, excitation and emission monochromators, and a Hamamatsu R928 photomultiplier tube and time-correlated single photon counting option. The emission and excitation spectra were corrected using standard calibration fits.

[0361] The excited state lifetime was determined using the TCSPC method with the FM-2013 instrument and the Horiba Yvon TCSPC hub using the same system.

[0362] Excitation source:

[0363] Nano LED 370 (wavelength: 371nm, pulse duration: 1.1ns)

[0364] Nano LED 290 (wavelength: 294nm, pulse duration: <1ns)

[0365] Spectrum LED 310 (wavelength: 314nm)

[0366] Spectrum LED 355 (wavelength: 355nm).

[0367] Data analysis (exponential fit) was done using the software suite DataStation and DAS6 analysis software. The fit was specified using the chi-square test.

[0368] Photoluminescence quantum yield measurement

[0369] For photoluminescence quantum yield (PLQY) measurements, an absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yield and CIE coordinates were determined using software U6039-05 version 3.6.0.

[0370] The emission maximum is given in nm, the quantum yield Φ is given in %, and the CIE coordinates are given as x-value, y-value.

[0371] Determine PLQY using the following protocol:

[0372] 1) Quality assurance: using anthracene in ethanol (known concentration) as a reference

[0373] 2) Excitation wavelength: Determine the absorption maximum of organic molecules and use this wavelength to excite organic molecules

[0374] 3) Measurement

[0375] The quantum yield was measured for samples of solution or film under nitrogen atmosphere. The yield was calculated using the equation:

[0376]

[0377] Among them, n 光子 represents photon counts and Int. represents intensity.

[0378] HPLC-MS

[0379] HPLC-MS analysis was performed on an HPLC by Agilent (1100 series) with MS detector (Thermo LTQ XL).

[0380] A typical HPLC method is as follows: Agilent reverse phase column 4.6 mm × 150 mm, particle size 3.5 μm (ZORBAX Eclipse Plus C18, 4.6×150 mm, 3.5 μm HPLC column). HPLC-MS measurements were performed at room temperature (rt) following a gradient.

[0381] Turnover

[0382]

[0383] The following solvent mixture was used:

[0384] Solvent A: <![CDATA[H 2 O(90%)]]> MeCN (10%) Solvent B: <![CDATA[H 2 O(10%)]]> MeCN (90%) Solvent C: THF (50%) MeCN (50%)

[0385] An injection volume of 5 μL was sampled from a solution having an analyte concentration of 0.5 mg / mL for measurement.

[0386] Ionization of the probe was performed using an atmospheric pressure chemical ionization (APCI) source in either positive (APCI+) or negative (APCI-) ionization mode.

[0387] Fabrication and characterization of optoelectronic devices

[0388] Optoelectronic devices (such as OLED devices) comprising organic molecules according to the invention can be manufactured via vacuum deposition. If a layer comprises more than one compound, the weight percentage of the one or more compounds is given in %. The total weight percentage value adds up to 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0389] The (not fully optimized) OLEDs were characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) was intensity dependent, calculated using the light detected by the photodiode and the current. The OLED device lifetime was extracted from the change in brightness during operation at a constant current density. The LT50 value corresponds to the time at which the measured brightness decreases to 50% of the initial brightness, similarly, the LT80 corresponds to the time point at which the measured brightness decreases to 80% of the initial brightness, the LT95 corresponds to the time point at which the measured brightness decreases to 95% of the initial brightness, etc.

[0390] (e.g., applying an increased current density) to perform accelerated lifetime measurements. Exemplarily, the following equation is used to determine 500 cd / m 2 The LT80 value is:

[0391]

[0392] Among them, L 0 represents the initial brightness at the applied current density.

[0393] Said value corresponds to the average of several (usually two to eight) pixels, giving the standard deviation between these pixels.

[0394] Example

[0395] Example 1

[0396]

[0397] Example 1 was synthesized according to AAV1 (yield 91%) and AAV2 (yield 31%), and E1 = (2-(9H-carbazol-9-yl)phenyl)boronic acid [1189047-28-6] and E2 = 1,3,6,8-tetramethyl-9H-carbazole [6558-85-6].

[0398] Figure 1 The emission spectrum of Example 1 (10 wt. % in PMMA) is depicted. max ) at 535 nm. The photoluminescence quantum yield (PLQY) is 56%, the full width at half maximum (FWHM) is 0.36 eV, and the emission lifetime is 1.33 μs. The resulting CIEx coordinate is 0.38 and the CIEy coordinate is 0.58.

[0399] 1 H NMR (300 MHz, dichloromethane-d 2 )δ8.78(d,J=8.8Hz,1H),8.59(d,J=8.6Hz,1H),8.51(dd,J=7.4,1.2Hz,1H),8.3 3(ddd,J=7.7,1.5,0.6Hz,1H),7.95(ddd,J=8.8,7.1,1.8Hz,1H),7.89–7.82(m, 3H),7.79(dd,J=7.6,1.8Hz,1H),7.72(ddd,J=8.6,7.3,1.4Hz,1H),7.57–7.49( m,2H),7.26(ddd,J=7.8,7.1,0.8Hz,1H),6.88(s,2H),2.50(s,6H),1.81(s,6H).

[0400] Example D1

[0401] Example 1 was tested in an OLED D1 which was produced with the following layer structure:

[0402]

[0403]

[0404] OLED D1 at 1000cd / m 2 The external quantum efficiency (EQE) of 16.7% was generated at 5.2 V. The emission maximum was at 542 nm and the FWHM was 75 nm at 5.2 V. The corresponding CIEx value was 0.387 and the corresponding CIEy value was 0.588.

[0405] Additional Examples of Inventive Organic Molecules

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

Claims

1. An organic molecule comprising a structure of formula Ib-3: in, R 5 is independently selected from the group consisting of: hydrogen; deuterium; and C1-C 40 alkyl, R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , R XI , R XII , R XIII , R XIV and R XV independently selected from the group consisting of: hydrogen; deuterium; and C1-C 40 alkyl.

2. The organic molecule according to claim 1, wherein R V and R XII Not all represent hydrogen.

3. The organic molecule according to claim 1, wherein R V , R VI , R VII , R VIII , R IX , R X , R XI and R XII independently selected from the group consisting of: hydrogen; deuterium; Me; i Pr; and t Bu.

4. The organic molecule according to claim 1, wherein R V =R XII and / or R X =R VII .

5. The organic molecule according to claim 1, comprising the following compounds:

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

7. The use according to claim 6, wherein: The optoelectronic device is selected from the group consisting of: Organic light emitting diodes; light emitting electrochemical cells; organic light emitting diode sensors; organic diodes; organic solar cells; organic transistors; organic field effect transistors; organic lasers; and down conversion components.

8. A composition comprising: (a) an organic molecule according to any one of claims 1 to 5, in the form of an emitter; and (b) an emitter and / or host material different from the organic molecule.

9. The composition according to claim 8, further comprising a dye and / or a solvent.

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

11. The optoelectronic device of claim 10, in the form of a device selected from the group consisting of an organic light emitting diode, a light emitting electrochemical cell, an organic light emitting diode sensor, an organic diode, an organic solar cell, an organic transistor, an organic field effect transistor, an organic laser, and a down conversion element.

12. The optoelectronic device according to claim 10 or 11, comprising: substrate; anode; and a cathode, wherein the anode or the cathode is disposed on the substrate; as well as The light emitting layer is disposed between the anode and the cathode and includes the organic molecule or the composition.

13. A method for manufacturing an optoelectronic device, wherein: Using an organic molecule according to any one of claims 1 to 5 or a composition according to claim 8 or 9, the method comprises the step of treating the organic molecule by vacuum evaporation or from solution.

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