Organic molecules for optoelectronic devices

Abstract

The present invention relates to a light-emitting organic molecule, particularly for application in optoelectronic devices. According to the invention, the organic molecule comprises a first chemical moiety having the structure of formula I and a second chemical moiety having the structure of formula II, where W is a single bond attachment site connecting the first chemical moiety to the second chemical moiety, and L is a linking group having the structure of formula BN-I, where the dashed line indicates the attachment site as depicted in formula I, and # indicates the attachment site between the first chemical moiety and the second chemical moiety. [Formula 1] JPEG2024513552000151.jpg2927 ...Chemical formula I [chemical 2] JPEG2024513552000152.jpg2641 ...Chemical formula II [C3] JPEG2024513552000153.jpg2222 ...Chemical formula BN-I

Description

[Technical field]

[0001] The present invention relates to light-emitting organic molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Summary of the Invention [Problem to be solved by the invention]

[0002] The problem that the present invention aims to solve is to provide molecules that are suitable for use in optoelectronic devices. [Means for solving the problem]

[0003] Such objectives are achieved by the present invention, which provides novel organic molecules.

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

[0005] According to the invention, the organic molecules exhibit a maximum emission in the sky blue, green or yellow spectral range, preferably in the green spectral range. The organic molecules exhibit a maximum emission in particular at 470-580 nm, preferably at 490-560 nm, more preferably at 500-560 nm, even more preferably at 510-550 nm, most preferably at 520-540 nm. The photoluminescence quantum yield of the organic molecules according to the invention is preferably 10% or more, more preferably 20% or more, even more preferably 30% or more, in particular 40% or more, particularly preferably 50% or more. The molecules according to the invention in particular exhibit thermally activated delayed fluorescence (TADF) materials. The use of the molecules according to the invention in optoelectronic devices, for example organic light-emitting diodes (OLEDs), leads to an even higher efficiency of the device. The corresponding OLEDs have higher stability than OLEDs with known emitter materials and similar hues and / or when using the molecules according to the invention in OLED displays, a more accurate reproduction of the naturally appearing hues, i.e. a higher resolution in the displayed images, is achieved. In particular, the molecules can be used in combination with fluorescent emitters to enable so-called hyper-fluorescence. [Brief description of the drawings]

[0006] [Figure 1] 1 is a graph showing the emission spectrum of Example 1 (10% by weight) in PMMA. [Diagram 2] 1 is a graph showing the emission spectrum of Example 2 (10 wt %) in PMMA. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] Organic molecules according to the invention The organic molecule according to the invention comprises or consists of: a first chemical moiety that comprises or consists of the structure of formula I, and [ka] ...Chemical formula I a second chemical moiety that comprises or consists of the structure of formula II, [ka] ...Chemical formula II Where: the first chemical moiety is attached to the second chemical moiety through a single bond; W is a single bond attachment site linking the first chemical moiety to the second chemical moiety; L is a bonding group having the structure of the following chemical formula BN-I, [ka] ...Chemical formula BN-I wherein the dashed line indicates the binding site represented in formula I, # indicates the site of attachment of the first chemical moiety to the second chemical moiety; Z, in each occurrence, independently, is a direct bond, CR 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3 , N.R. 3 , O, SiR 3 R 4 , S, S(O) and S(O) 2 is selected from the group consisting of R 1 and R 2 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, CN, CF 3 , phenyl, C 1 -C 5 Alkyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; C 2 -C 8 Alkenyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; C2 -C 8 Alkynyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; Optionally, R is 1 or more 6 C replaced with 6 -C 18 Aryl, and Optionally, R is 1 or more 6 C replaced with 3 -C 17 Heteroaryl, R a , R 3 and R 4 are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , C.N., F, Br, I, C 1 -C 40 Alkyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R.5 , O, S or CONR 5 is selectively substituted with C 1 -C 40 Alkoxy, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 1 -C 40 Thioalkoxy, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 2 -C 40 Alkenyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 2 -C 40 Alkynyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with Optionally, R is 1 or more 5 C replaced with 6 -C 60 Aryl, and Optionally, R is 1 or more 5 C replaced with 3 -C 57 Heteroaryl, R 5 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R 6 ) 2 , OR 6 , Si(R 6 ) 3 , B(OR 6 ) 2 , O.S.O. 2 R 6, C.F. 3 ,CN,F,Br,I, C 1 -C 40 Alkyl, This is represented by one or more substituents R 6 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is selectively substituted with C 1 -C 40 Alkoxy, This is represented by one or more substituents R 6 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is selectively substituted with C 1 -C 40 Thioalkoxy, This is represented by one or more substituents R 6 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 6 C=CR 6 , C≡C, Si(R6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is selectively substituted with C 2 -C 40 Alkenyl, This is represented by one or more substituents R 6 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is selectively substituted with C 2 -C 40 Alkynyl, This is represented by one or more substituents R 6 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 6 C=CR 6 , C≡C, Si(R 6 ) 2 , Ge(R 6 ) 2 , Sn(R 6 ) 2 , C=O, C=S, C=Se, C=NR 6 , P(=O)(R 6 ), SO, SO 2 , N.R. 6 , O, S or CONR 6 is selectively substituted with Optionally, R is 1 or more 6 C replaced with 6 -C 60 Aryl, and Optionally, R is 1 or more 6 C replaced with 3 -C 57 Heteroaryl, R 6 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, halogens, OPh, CF 3 ,C.N.,F. C 1 -C 5 Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 1 -C 5 Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 1 -C 5 Thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 2 -C 5 Alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, C 2 -C 5 Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF 3 or replaced by F, Optionally, 1 or more C 1 -C 5 C substituted with alkyl substituents 6 -C 18 Aryl, Optionally, 1 or more C 1 -C 5C substituted with alkyl substituents 3 -C 17 Heteroaryl, N(C 6 -C 18 Aryl) 2 , N(C 3 -C 17 Heteroaryl) 2 , and N(C 3 -C 17 Heteroaryl)(C 6 -C 18 aryl), Here, the substituent R a , R 3 , R 4 or R 5 are, independently of one another, one or more substituents R a , R 3 , R 4 or R 5 with the aryloxy group, selectively forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system.

[0008] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of: [ka] ...Chemical formula IIIa [ka] ...Chemical formula IIIb [ka] ...Chemical formula IIIc [ka] ...Chemical formula IIId

[0009] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IIIa and Formula IIIb.

[0010] In one embodiment, R 1 and R 2 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, CN, CF 3 , phenyl, C 1 -C 5 Alkyl, Optionally, R is 1 or more 6 C replaced with 6 -C 18 Aryl, and Optionally, R is 1 or more 6 C replaced with 3 -C 17 Heteroaryl. In one embodiment, R 1 and R 2 are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, CN, CF 3 , phenyl, C 1 -C 5 Alkyl, and Optionally, R is 1 or more 6 C replaced with 6 -C 18 Aryl.

[0011] In one embodiment, R 1 and R 2 are in each case, independently of one another, hydrogen, deuterium, methyl, CN, CF 3 and phenyl.

[0012] In one embodiment, R 1 and R 2 are, in each occurrence independently of one another, selected from the group consisting of hydrogen, methyl and phenyl.

[0013] In one embodiment, R 1 is hydrogen in each case.

[0014] In one embodiment, R 2 is hydrogen in each case.

[0015] In one embodiment, R 1 and R 2 is hydrogen in each case.

[0016] In a further embodiment of the invention, the second chemical moiety comprises or consists of the structure of formula IIa: [ka] ...Chemical formula IIa where # and R a is defined as above.

[0017] In one embodiment of the present invention, at least one R a is not hydrogen.

[0018] In one embodiment of the present invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 , where two or more adjacent substituents R a is substituted with a ring system selected from the group consisting of: [ka] where each dashed line represents one of the ring systems shown above separated by two adjacent substituents R a represents a direct bond attached to position 104, allowing the ring system depicted above to be fused to a second chemical moiety depicted in formula II.

[0019] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , One or more substituents R 5 Ph selectively substituted with One or more substituents R 5 pyridinyl optionally substituted with One or more substituents R 5 pyrimidinyl optionally substituted with One or more substituents R 5 carbazolyl optionally substituted with One or more substituents R 5 triazinyl optionally substituted with One or more substituents R 5 Selectively substituted N(Ph) 2 , where any two adjacent substituents R a are optionally joined together to form a ring system selected from the group consisting of: [ka] where X 1 is S, O or NR 5 It is.

[0020] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me,i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 , where any two adjacent substituents R a are optionally joined together to form a ring system selected from the group consisting of: [ka] Where X 1 is S, O or NR 5 It is.

[0021] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 , where any two adjacent substituents R a are optionally joined together to form a ring system selected from the group consisting of: [ka] Where X 1 is S, O or NR 5 It is.

[0022] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 , where any two adjacent substituents R a are optionally joined together to form a ring system selected from the group consisting of: [ka] .

[0023] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, N(Ph) 2 .

[0024] In a further embodiment of the invention, R a are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph.

[0025] In one embodiment of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, tBu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 , where two or more adjacent substituents R 5 or one or more substituents R a One or more substituents R adjacent to 5 is replaced by a ring system selected from the group consisting of: [ka] wherein each dashed line represents an adjacent substituent R substituted by said fused ring system. 5 , or R 5 and R a represents a direct bond connecting one of said fused ring systems to the position to which is attached.

[0026] In certain embodiments of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: hydrogen, Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, iPr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph), 2 .

[0027] In a preferred embodiment of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: hydrogen, One or more substituents R 6 C selectively substituted with 1 -C 40 Alkyl, One or more substituents R 6 C selectively substituted with 3 -C 57 Heteroaryl, and One or more substituents R 6 C selectively substituted with 6 -C 60 Aryl. In certain embodiments of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: hydrogen, One or more substituents R 6 C selectively substituted with 1 -C 40 Alkyl, and One or more substituents R 6 C selectively substituted with 6 -C 60 Aryl. In certain embodiments of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: hydrogen, One or more substituents R 6 C selectively substituted with 1 -C 4 Alkyl, and One or more substituents R 6 Optionally substituted phenyl (Ph). In certain embodiments of the present invention, R 5 are, in each occurrence, independently selected from the group consisting of: Hydrogen, Me, i Pr, t Bu, CN, CF 3 , and Me, i Pr, t Bu, CN, CF 3 and Ph optionally substituted with one or more substituents independently selected from the group consisting of Ph. In one embodiment of the invention, the second chemical moiety comprises or consists of a structure of formula IIa-1, a structure of formula IIa-2, a structure of formula IIa-3, or a structure of formula IIa-4: [ka] ...Chemical formula IIa-1 [ka] ...Chemical formula IIa-2 [ka] ...Chemical formula IIa-3 [ka] ...Chemical formula IIa-4

[0028] In further embodiments of the invention, the second chemical moiety comprises or consists of a structure of formula IIb-1, a structure of formula IIb-2, a structure of formula IIb-3, or a structure of formula IIb-4: [ka] ...Chemical formula IIb-1 [ka] ...Chemical formula IIb-2 [ka] ...Chemical formula IIb-3 [ka] ...Chemical formula IIb-4 Where: R b are, in each occurrence, independently selected from the group consisting of: deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 , CF 3 , C.N., F, Br, I, C 1 -C 40 Alkyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 1 -C 40 Alkoxy, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 1 -C 40 Thioalkoxy, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 2 -C 40 Alkenyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 2 -C 40 Alkynyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with Optionally, R is 1 or more 5C replaced with 6 -C 60 Aryl, and Optionally, R is 1 or more 5 C replaced with 3 -C 57 Heteroaryl, Otherwise the above definitions apply.

[0029] In a further embodiment of the invention, the second chemical moiety comprises or consists of a structure of formula IIc-1, a structure of formula IIc-2, a structure of formula IIc-3, or a structure of formula IIc-4, [ka] ...Chemical formula IIc-1 [ka] ...Chemical formula IIc-2 [ka] ...Chemical formula IIc-3 [ka] ...Chemical formula IIc-4 Here, the above definitions apply.

[0030] In a further embodiment of the invention, R b are, in each occurrence, independently selected from the group consisting of: Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph; Me, i Pr, t Bu, CN, CF 3 and Ph, N(Ph) 2 .

[0031] In a further embodiment of the invention, R b are, in each occurrence, independently selected from the group consisting of: Me, i Pr, t Bu, C.N., CF 3 , Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph, Me, iPr, t Bu, CN, CF 3 and Ph.

[0032] In a further embodiment of the invention, R b are, in each occurrence, independently selected from the group consisting of: Me, t Bu, Me, i Pr, t Bu, CN, CF 3 and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph, Me, i Pr, t Bu, CN, CF 3 and Ph.

[0033] In a further embodiment of the invention, R b are, in each occurrence, independently selected from the group consisting of: Me, t Bu, Me, i Pr, t Bu, CN, CF 3 Ph optionally substituted with one or more substituents independently selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph.

[0034] In one embodiment, the second chemical moiety comprises or consists of any one of the following structures: [ka] [ka] [ka] [ka] JPEG2024513552000032.jpg56123 [ka] [ka] [ka] [ka] where the above definitions apply to #, Z, and R a , R 3 , R 4 and R 5 This applies to.

[0035] In one embodiment, R a and R 5 are in each case independently of one another hydrogen (H), methyl (Me), i-propyl (CH(CH 3 ) 2 )( i Pr), t-Butyl ( t Bu), Phenyl (Ph), CN, CF 3 and diphenylamine (NPh 2).

[0036] In one embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of: [ka] ...Chemical formula IVa [ka] ...Chemical formula IVb [ka] ...Chemical formula IVc [ka] ...Chemical formula IVd .

[0037] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula IVa and Formula IVb.

[0038] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formula IVa-1, formula IVb-1, formula IVc-1, and formula IVd-1: [ka] Chemical formula IVa-1 [ka] Chemical formula IVb-1 [ka] Chemical formula IVc-1 [ka] Chemical formula IVd-1.

[0039] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of: Va, Vb, Vc, and Vd: [ka] ...Chemical formula Va [ka] ...Chemical formula Vb [ka] ...Chemical formula Vc [ka] ...Chemical formula Vd .

[0040] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula Va and Formula Vb.

[0041] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of: Formula Va-1, Formula Vb-1, Formula Vc-1, and Formula Vd-1: [ka] ...Chemical formula Va-1 [ka] ...Chemical formula Vb-1 [ka] Vc-1 [ka] ...Chemical formula Vd-1.

[0042] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of: Formula Va-2, Formula Vb-2, Formula Vc-2, and Formula Vd-2: [ka] ...Chemical formula Va-2 [ka] ...Chemical formula Vb-2 [ka] ...Chemical formula Vc-2 [ka] ...Chemical formula Vd-2.

[0043] In one embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of: [ka] ...Chemical formula VIa [ka] ...Chemical formula VIb [ka] ...Chemical formula VIc [ka] ...Chemical formula VId.

[0044] In a preferred embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of Formula VIa and Formula VIb.

[0045] In one embodiment of the present invention, the organic molecule comprises or consists of a structure selected from the group consisting of formula VIa-1, formula VIb-1, formula VIc-1, and formula VId-1, where R b is defined as above: [ka] ...Chemical formula VIa-1 [ka] ...Chemical formula VIb-1 [ka] ...Chemical formula VIc-1 [ka] ...Chemical formula VId-1 .

[0046] In one embodiment of the invention, the organic molecule comprises or consists of a structure selected from the group consisting of formula VIa-2, formula VIb-2, formula VIc-2, and formula VId-2, where R b is defined as above: [ka] ...Chemical formula VIa-2 [ka] ...Chemical formula VIb-2 [ka] ...Chemical formula VIc-2 [ka] ...Chemical formula VId-2 .

[0047] In particular embodiments of the organic molecule, R b are, in each occurrence, independently selected from the group consisting of: Deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , O.S.O. 2 R 5 , C.F. 3 ,CN,F,Br,I, C 1 -C 40 Alkyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR5 is selectively substituted with C 1 -C 40 Alkoxy, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 1 -C 40 Thioalkoxy, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 2 -C 40 Alkenyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with C 2 -C 40 Alkynyl, This is represented by one or more substituents R 5 is selectively substituted with Here, one or more non-adjacent CH 2 The group is R 5 C=CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C=O, C=S, C=Se, C=NR 5 , P(=O)(R 5 ), SO, SO 2 , N.R. 5 , O, S or CONR 5 is selectively substituted with Optionally, R is 1 or more 5 C replaced with 6 -C 60 Aryl, and Optionally, R is 1 or more 5 C replaced with 3 -C 57 Heteroaryl.

[0048] definition The term "layer" as used herein refers broadly to a body or sheet-like mass having a planar shape. An optoelectronic device is composed of multiple layers.

[0049] In the context of the present invention, an emissive layer (EML) is a layer of an optoelectronic device, where emission from said layer is observed upon application of a voltage and current to the device. One skilled in the art will appreciate that emission from an optoelectronic device is due to emission from at least one EML. A skilled artisan will appreciate that emission from an EML is typically not due (predominantly) to all materials contained in the EML, a particular emitter material.

[0050] In the context of the present invention, an "emitter material" (also referred to as "emitter") is a material that emits light when included in an emissive layer (EML) of an optoelectronic device under given voltage and electrical conditions. A current is applied to the device. Emitter materials are generally "emissive dopant" materials. A dopant material (whether emissive or not) is a material that is incorporated into a matrix material, referred to herein as a host material. Here, the host material, when included in an optoelectronic device such as an OLED comprising at least one organic molecule according to the present invention, is generally a H B It is called.

[0051] In the context of the present invention, the term "cyclic group" is understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0052] In the context of the present invention, when referring to a chemical structure, the term "ring" is understood in the broadest sense as any monocyclic moiety. In the same respect, when referring to a chemical structure, the term "ring" is understood in the broadest sense as any bicyclic or polycyclic moiety.

[0053] In the context of the present invention, "ring system" is also understood in the broadest sense as any monocyclic, bicyclic or polycyclic moiety.

[0054] In the context of this invention, the term "ring atom" refers to any atom that is part of the cyclic core of a ring or ring system and is not part of an acyclic substituent optionally attached to the cyclic core.

[0055] In the context of the present invention, the term "carbocycle" is understood in its broadest sense as any cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen or any other substituent as defined in certain embodiments of the present invention. The term "carbocyclic" is also understood as an adjective and refers to a cyclic group whose cyclic core structure contains only carbon atoms which may be substituted with hydrogen or any other substituent as defined in certain embodiments of the present invention.

[0056] In the context of the present invention, the term "heterocycle" is understood in the broadest sense as any cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The term "heterocyclic" is also understood as an adjective and refers to a cyclic group whose cyclic core structure contains not only carbon atoms but also at least one heteroatom. The heteroatoms can be the same or different in each case, unless otherwise specified in a specific embodiment, and can be individually selected from the group consisting of B, Si, N, O, S and Se, more preferably B, N, O and S, most preferably N, O and S. It goes without saying that all carbon atoms or heteroatoms contained in a heterocycle in the context of the present invention can be substituted with hydrogen or any other substituent defined in a specific embodiment of the present invention.

[0057] One of ordinary skill in the art can recognize that any cyclic group (ie, any carbocyclic and heterocyclic ring) may be aliphatic, aromatic or heteroaromatic.

[0058] In the context of the present invention, when referring to a cyclic group (i.e., ring, ring system, carbocyclic ring, heterocyclic ring), the term "aliphatic" includes one or more ring atoms that are not part of an aromatic or heteroaromatic ring or ring system of the cyclic core structure (not including optional attached substituents). Preferably, most of the ring atoms, more preferably all of the ring atoms in the aliphatic cyclic group are not part of an aromatic or heteroaromatic ring or ring system (e.g., in cyclohexane or piperidine). Here, when referring to an aliphatic ring or ring system in general, no distinction is made between a carbocyclic group and a heterocyclic group, and the term "aliphatic" is also used as an adjective to describe a carbocyclic or heterocyclic ring to indicate whether a heteroatom is included in the aliphatic ring group.

[0059] As will be understood by the skilled artisan, the terms "aryl" and "aromatic" are understood in the broadest sense to refer to any monocyclic, bicyclic or polycyclic aromatic moiety, i.e., a ring group in which all ring atoms are part of an aromatic ring system, preferably as part of the same aromatic ring system. However, throughout this application, the terms "aryl" and "aromatic" are restricted to monocyclic, bicyclic or polycyclic aromatic moieties in which all aromatic ring atoms are carbon atoms. In contrast, in this application, the terms "heteroaryl" and "heteroaromatic" refer to any monocyclic, bicyclic or polycyclic aromatic moiety in which one or more aromatic carbon ring atoms are replaced by a heteroatom (i.e., not carbon). Unless otherwise stated in a particular embodiment of the present invention, at least one heteroatom in a "heteroaryl" or "heteroaromatic" may be the same or different in each case and may be individually selected from the group consisting of N, O, S and Se, more preferably N, O and S. One of ordinary skill in the art will appreciate that the adjectives "aromatic" and "heteroaromatic" are also used to describe any cyclic group (i.e., any ring system), i.e., an aromatic cyclic group (i.e., an aromatic ring system) is an aryl group, and a heteroaromatic cyclic group (i.e., a heteroaromatic ring system) is a heteroaryl group.

[0060] Unless otherwise specified in a particular embodiment of the present invention, in the present application, an aryl group preferably comprises 6 to 60 aromatic ring atoms, more preferably 6 to 40 aromatic ring atoms, even more preferably 6 to 18 aromatic ring atoms. Unless otherwise specified in a particular embodiment of the present invention, in the present application, a heteroaryl group preferably comprises 5 to 60 aromatic ring atoms, more preferably 5 to 40 aromatic ring atoms, even more preferably 5 to 20 aromatic ring atoms, at least one of which is a heteroatom, preferably selected from N, O, S and Se, more preferably N, O and S. When one or more heteroatoms comprise a heteroaromatic group, all heteroatoms are preferably selected, independently of one another, from N, O, S and Se, more preferably N, O and S.

[0061] In the context of the present invention, for both aromatic and heteroaromatic groups (e.g., aryl or heteroaryl substituents), the number of aromatic ring carbon atoms is indicated by a subscript number in the definition of the particular substituent, e.g., "C 6 -C 60 The term "aryl" is used in the form "aryl" which means that each aryl substituent contains from 6 to 60 aromatic carbon ring atoms. The same subscript numbers are used to indicate the number of carbon atoms permitted in all other types of substituents, whether aliphatic, aromatic, or heteroaromatic. For example, "C 1 -C 40 The term "alkyl" refers to an alkyl substituent containing from 1 to 40 carbon atoms.

[0062] Preferred examples of aryl groups include benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, or combinations of these groups.

[0063] Preferred examples of heteroaryl groups are furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; pyrrole, indole, isoindole, carbazole, indolocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, azole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-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, 1,2,4,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or combinations of these groups.

[0064] The term "arylene" as used throughout this application refers to a divalent aryl substituent that possesses two attachment sites and serves as a linker structure to another molecular structure. In the same vein, the term "heteroarylene" refers to a divalent aryl substituent that possesses two attachment sites and serves as a linker structure to another molecular structure.

[0065] In the context of the present invention, when referring to an aromatic or heteroaromatic ring system, the term "fused" means that the "fused" aromatic or heteroaromatic rings share at least one bond that is part of both ring systems. For example, naphthalene (or naphthyl when referred to as a substituent) or benzothiophene (or benzothiophenyl when referred to as a substituent) are considered as fused aromatic ring systems in the context of the present invention, where the two benzene rings (in the case of naphthalene) or thiophene and benzene (in the case of benzothiophene) share one bond. Sharing a bond in such a context is also understood to include sharing the two atoms that constitute each bond, and a fused aromatic or heteroaromatic ring system is also understood as one aromatic or heteroaromatic system. It is also understood that one or more bonds are shared by the aromatic or heteroaromatic rings that constitute the fused aromatic or heteroaromatic ring system (e.g., in pyrene). An aliphatic ring system may also be fused, which will be understood to have the same meaning as an aromatic or heteroaromatic ring system, except that a fused aliphatic ring system is not aromatic. An aromatic or heteroaromatic ring system may also be fused (i.e., share at least one bond) with an aliphatic ring system.

[0066] In the context of this invention, the term "condensed" ring system has the same meaning as a "fused" ring system.

[0067] In certain embodiments of the invention, adjacent substituents attached to a ring or ring system can form a further monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system fused to the aromatic or heteroaromatic ring or ring system to which said substituents are attached. Optionally, the fused ring system so formed is also understood to be larger (meaning containing more ring atoms) than the aromatic or heteroaromatic ring or ring system to which the adjacent substituents are attached. In that case (and when such a number is provided), the "total" number of ring atoms contained in the fused ring system must be understood to be the sum of the ring atoms contained in the aromatic or heteroaromatic ring or ring system. Although adjacent substituents are bonded and the ring atoms of the additional ring system are formed by the adjacent substituents, the ring atoms shared by the fused rings are counted once, not twice. For example, a benzene ring can have two adjacent substituents forming yet another benzene ring, such that a naphthalene core is formed. The naphthalene core will contain 10 ring atoms, since two carbon atoms are shared by the two benzene rings and counted only once, not twice. In this context, the term "adjacent substituents" means substituents that are attached to the same or adjacent atoms.

[0068] Generally, in the context of the present invention, the term "adjacent substituents" or "adjacent groups" means substituents or groups which are attached to the same or adjacent atoms.

[0069] In the context of the present invention, the term "alkyl group" is understood in the broadest sense as any linear, branched or cyclic alkyl substituent. In particular, the term "alkyl" refers to the substituents methyl (Me), ethyl (Et), n-propyl (N-propyl ... n Pr), i-propyl ( i Pr), cyclopropyl, n-butyl ( n Bu), i-Butyl ( i Bu), s-Butyl ( s Bu), t-Butyl ( tBu), cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n -octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo[2,2,2]octyl, 2-bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl, 1,1-dimethyl-n-hept-1-yl, 1,1-dimethyl-n-oct-1-yl, 1,1-dimethyl-n- des-1-yl, 1,1-dimethyl-n-dodec-1-yl, 1,1-dimethyl-n-tetradec-1-yl, 1,1-dimethyl-n-hexades-1-yl, 1,1-dimethyl-n-octadec-1-yl, 1,1-diethyl-n-hex-1-yl, 1,1-diethyl-n-hept-1-yl, 1,1-diethyl-n-oct-1-yl, 1,1-diethyl-n-dec-1-yl, 1,1-diethyl-n-dodec- 1-yl, 1,1-diethyl-n-tetradec-1-yl, 1,1-diethyl-n-hexadec-1-yl, 1,1-diethyl-n-octadec-1-yl, 1-(n-propyl)-cyclohex-1-yl, 1-(n-butyl)-cyclohex-1-yl, 1-(n-hexyl)-cyclohex-1-yl, 1-(n-octyl)-cyclohex-1-yl and 1-(n-decyl)-cyclohex-1-yl.

[0070] For example, in s-butyl, s-pentyl, and s-hexyl, the "s" means "secondary", i.e., s-butyl, s-pentyl, and s-hexyl are the same as sec-butyl, sec-pentyl, and sec-hexyl, respectively. For example, in t-butyl, t-pentyl, and t-hexyl, the "t" means "tertiary", i.e., t-butyl, t-pentyl, and t-hexyl are the same as tert-butyl, tert-pentyl, and tert-hexyl, respectively.

[0071] As used throughout this specification, the term "alkenyl" includes linear, branched and cyclic alkenyl substituents. The term "alkenyl group" includes, for example, the substituents ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.

[0072] As used throughout this specification, the term "alkynyl" includes linear, branched and cyclic alkynyl substituents. The term "alkynyl group" includes, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.

[0073] As used throughout this specification, the term "alkoxy" includes linear, branched and cyclic alkoxy substituents. The term "alkoxy group" includes, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy and 2-methylbutoxy.

[0074] The term "thioalkoxy" as used throughout this specification includes linear, branched and cyclic thioalkoxy substituents, where the O in the exemplary alkoxy group is replaced with an S.

[0075] The term "halogen" (or, when referring to a substituent in chemical nomenclature, "halo") as used throughout this specification is also understood in its broadest sense to be any atom of an element of the seventh main group (i.e., group 17) of the Periodic Table of the Elements, preferably fluorine, chlorine, bromine or iodine.

[0076] When a molecular fragment is described as being attached to a substituent or other moiety, the name may be described as just the fragment (e.g., naphthyl, dibenzofuryl) or as the whole molecule (e.g., naphthalene, dibenzofuran). As used herein, the above modes of describing a substituent or attached fragment are considered equivalent.

[0077] In addition, in this application, "C 6 -C 60 aryl" or "C 1 -C 40 Whenever a substituent such as "alkyl" is referred to without a name indicating the point of attachment within that substituent, this means that the respective substituent may be attached via any atom. For example, "C 6 -C 60 An "aryl" substituent is attached via any 6 to 60 aromatic carbon atoms and is defined as "C 1 -C 40 An "alkyl" substituent is attached via any 1-40 aliphatic carbon atoms, while a "2-cyanophenyl" substituent is attached only in a manner such that its C-N group is adjacent to the site of attachment in a manner that allows for accurate chemical nomenclature.

[0078] In the context of the present invention, whenever a substituent such as "butyl", "biphenyl" or "terphenyl" is mentioned without further specification, this means that any isomer of the respective substituent is acceptable for that particular substituent. In this regard, for example, the term "butyl" as a substituent includes n-butyl, s-butyl, t-butyl and iso-butyl as substituents. Similarly, the term "biphenyl" as a substituent includes ortho-biphenyl, meta-biphenyl or para-biphenyl, where ortho, meta and para are defined with respect to the point of attachment of the biphenyl substituent to the respective chemical moiety bearing the biphenyl substituent. Similarly, the term "terphenyl" includes as substituents 3-ortho-terphenyl, 4-ortho-terphenyl, 4-meta-terphenyl, 5-meta-terphenyl, 2-para-terphenyl or 3-para-terphenyl, where ortho, meta and para indicate the positions of the two Ph moieties in the terphenyl group relative to each other, and "2-", "3-", "4-" and "5-" indicate the attachment positions of the terphenyl substituent to the respective chemical moiety bearing the terphenyl substituent, as known to the skilled artisan.

[0079] It is understood that all of the groups, and indeed all chemical moieties, defined above, whether cyclic or acyclic, aliphatic, aromatic or heteroaromatic, may be further substituted by the specific embodiments described herein.

[0080] In this embodiment, where groups are defined differently from the general definition given herein, the definition in this embodiment applies.

[0081] All hydrogen atoms (H) contained in any structure referred to in this application are also replaced, in each case independently of one another, with deuterium (D), unless specifically stated otherwise. The replacement of hydrogen with deuterium is common practice and will be apparent to those skilled in the art.

[0082] When comparing experimental or calculated data, values ​​must be determined by the same methodology. For example, a specified method must be used to determine the experimental ΔE ST is determined to be less than 0.4 eV, the comparison is only valid if the same specific method involving the same conditions is used. As a specific example, a comparison of the photoluminescence quantum yield (PLQY) of different compounds is only valid if the PLQY determinations are performed using the same protocol under the same reaction conditions (e.g., measurements at room temperature on 10% PMMA film). Also, the calculated energy values ​​are determined using the same calculation method (same functions and same standard settings).

[0083] Hyperfluorescence is a concept related to light emission from optoelectronic devices, especially OLEDs, where at least one emissive layer comprises one or more TADF materials and one or more fluorescent emitters. In hyperfluorescence, at least one TADF material can convert a triplet excited state to a singlet excited state by reverse-intersystem-crossing (RISC) and emit light after transferring the excitation energy to at least one fluorescent emitter. This allows for the harvesting of triplet excitons for efficient fluorescence generation.

[0084] Optoelectronic devices comprising organic molecules according to the invention A further aspect of the invention relates to an optoelectronic device comprising an organic molecule according to the invention.

[0085] In one embodiment of an optoelectronic device comprising an organic molecule according to the invention, the organic molecule is selected from the group consisting of: Organic Light Emitting Diode (OLED) Light-emitting electrochemical cells OLED sensors, especially gas and vapor sensors that are not completely isolated from the outside Organic diode ·Organic solar cells Organic transistors Organic field-effect transistors Organic Lasers Down conversion element.

[0086] The light-emitting electrochemical cell consists of three layers: a cathode, an anode and an active layer comprising the organic molecules according to the invention.

[0087] In a preferred embodiment, the optoelectronic device comprising the organic molecules according to the invention is 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.

[0088] In a more preferred embodiment, the optoelectronic device comprising the organic molecules according to the present invention is an organic light emitting diode (OLED).

[0089] In one embodiment, the optoelectronic device comprising the organic molecules according to the invention is an OLED having the following layer structure: 1. Substrate 2. Anode layer A 3. Hole injection layer (HIL) 4. Hole transport layer (HTL) 5.Electron blocking layer (EBL) 6. Emitting layer (EML) 7. Hole Blocking Layer (HBL) 8.Electron transport layer (ETL) 9.Electron injection layer (EIL) 10. Cathode layer C

[0090] Here, the OLED (having an inverted stacked layer structure) optionally includes each layer except for the anode layer A, the cathode layer C, and the light-emitting layer EML, and different layers are combined, and the OLED also includes one or more layers of each layer type defined above.

[0091] Optoelectronic devices comprising at least one organic molecule according to the present invention may also optionally include one or more protective layers to protect the device from damaging exposure to harmful substances in the environment including, for example, moisture, vapors and / or gases.

[0092] In one embodiment of the present invention, the optoelectronic device comprising the organic molecules according to the present invention is an OLED having the following inverted layer structure: 1. Substrate 2. Cathode layer C 3.Electron injection layer (EIL) 4.Electron transport layer (ETL) 5. Hole Blocking Layer (HBL) 6. Light-emitting layer B 7.Electron blocking layer (EBL) 8. Hole transport layer (HTL) 9. Hole injection layer (HIL) 10. Anode layer A

[0093] Here, the OLED may optionally include each layer except for the anode layer A, the cathode layer C, and the light-emitting layer EML, and different layers may be combined, and the OLED may include one or more layers of each layer type defined above.

[0094] The organic molecules according to the invention (according to the above-mentioned embodiments) can be used in various layers depending on the exact structure and substitution. For application, in each layer of an optoelectronic device, in particular an OLED, the fraction of the organic molecules according to the invention is 0.1-99% by weight (weight percentage), more particularly 1-80% by weight. In an alternative embodiment, in each layer, the proportion of the organic molecules is 100% by weight.

[0095] In one embodiment, the optoelectronic device comprising the organic molecules according to the present invention is an OLED that can have a stacked structure. In said structure, individual units are stacked on top of each other, unlike the common arrangement in which OLEDs are arranged side by side. Mixed light is generated by the OLED that exhibits a stacked structure, and in particular, white light is generated by stacking a blue OLED, a green OLED and a red OLED. The OLED that exhibits a stacked structure may also include a charge generation layer (CGL), which is generally located between two OLED subunits and is generally configured as an n-doped layer and a p-doped layer. Generally, the n-doped layer of one CGL is located closer to the anode layer.

[0096] In one embodiment, the optoelectronic device comprising the organic molecules according to the present invention is an OLED comprising two or more light-emitting layers between an anode and a cathode.In particular, the so-called tandem OLED comprises three light-emitting layers, where one light-emitting layer emits red light, one light-emitting layer emits green light, and one light-emitting layer emits blue light, and may optionally comprise additional layers between each light-emitting layer, such as a charge generation layer, a charge blocking layer, or a charge transport layer.In a further embodiment, the light-emitting layers are stacked adjacent to each other.In a further embodiment, the tandem OLED comprises a charge generation layer between each two light-emitting layers.Also, adjacent light-emitting layers or light-emitting layers separated by a charge generation layer can be merged.

[0097] In one embodiment, an optoelectronic device comprising an organic molecule according to the invention is also an essentially white optoelectronic device, meaning that the device emits white light. For example, such a white optoelectronic device may also comprise at least one (deep) blue emitter molecule and one or more emitter molecules emitting green and / or red light. There may then be selective energy transfer between the two or more molecules, as explained later in this text.

[0098] In the case of an optoelectronic device comprising an organic molecule according to the invention, at least one organic molecule according to the invention is included in the light-emitting layer (EML) of the optoelectronic device, most preferably in the EML of an OLED. However, the organic molecule according to the invention is also used, for example, in an electron transport layer (ETL) and / or an electron blocking layer (EBL) or an exciton blocking layer and / or a hole transport layer (HTL) and / or a hole blocking layer (HBL). For application, the fraction of the organic molecule according to the invention in each layer of the optoelectronic device, in particular an OLED, is 0.1-99% by weight, more particularly 1-80% by weight. In an alternative embodiment, in each layer, the proportion of the organic molecule is 100% by weight.

[0099] The selection criteria of materials suitable for the individual layers of optoelectronic devices, in particular OLEDs, form part of the common knowledge of the person skilled in the art. The state of the art shows many substances used for the individual layers, informing which substances are suitable for use alongside each other. It is understood that any substance used in the state of the art can also be used in optoelectronic devices comprising organic molecules according to the invention. Below, preferred examples of substances for the individual layers will be given. As mentioned above, it is understood that this does not mean that all types of layers listed below must be present in an optoelectronic device comprising at least one organic molecule according to the invention. Furthermore, it is understood that an optoelectronic device comprising at least one organic molecule according to the invention comprises one or more of the respective layers listed below, such as for example two or more light-emitting layers (EMLs). It is also understood that two or more layers of the same type (for example two or more EMLs, or two or more HTLs) do not necessarily comprise the same substances, or even more preferably the same substances in the same proportions. Also, an optoelectronic device comprising at least one organic molecule according to the invention does not necessarily comprise all the types of layers listed below, where an anode layer, a cathode layer and an emissive layer are generally present in all cases.

[0100] The substrate is made of any material or composition of materials. Mostly, a glass slide is used as the substrate. Alternatively, a thin metal layer (e.g. copper, gold, silver or aluminum film) or a plastic film or a plastic slide can be used, which allows a higher level of flexibility. The anode layer A is made of a material that allows obtaining an almost (essentially) transparent film. To allow light emission from the OLED, at least one of the two electrodes must be (essentially) transparent, so that either the anode layer A or the cathode layer C is transparent. Preferably, the anode layer A is rich in or consists of transparent conductive oxides (TCOs). Such anode layers A may, for example, comprise indium tin oxide, aluminum zinc oxide, fluorine doped tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene.

[0101] Preferably, the anode layer A is (essentially) indium tin oxide (ITO) (e.g., (InO 3 ) 0.9 (SnO 2 ) 0.1 The roughness of the anode layer A due to the transparent conducting oxide (TCO) is also mitigated by using a hole injection layer (HIL). The HIL also facilitates the injection of similar charge carriers (i.e. holes) in that the transport of similar charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) is made of poly-3,4-ethylenedioxythiophene (PEDOT), polystyrenesulfonic acid (PSS), MoO 2 , V 2 O 5, CuPC or CuI, in particular a mixture of PEDOT and PSS. The hole injection layer (HIL) can also prevent diffusion of metals from the anode layer A into the hole transport layer (HTL). For example, the HIL can be poly-3,4-ethylenedioxythiophene:polystyrenesulfonate (PEDOT:PSS), poly-3,4-ethylenedioxythiophene (PEDOT), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (mMTDATA), 2,2',7,7'-tetrakis(n,n-diphenylamino)-9,9'-spirobifluorene (Spiro-TAD), N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine (DNTPD), N,N'-nis-(1-naphthalene-2-yl)phenylamine (NAPH), N,N'-bis ... It is also composed of N,N'-triphenyl-N,N'-bis-(1,1'-biphenyl)-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), N,N,N',N'-tetrakis(4-methoxyphenyl)benzidine (MeO-TPD), 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) and / or N,N'-diphenyl-N,N'-bis-(1-naphthyl)-9,9'-spirobifluorene-2,7-diamine (Spiro-NPD).

[0102] Adjacent to the anode layer A or the hole injection layer (HIL) is generally a hole transport layer (HTL). Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazoles are also 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) is also an electron blocking layer (EBL). Preferably, the hole transport compound has a triplet state T1 with a relatively high energy level. For example, the hole transport layer (HTL) may be tris(4-carbazolyl-9-ylphenyl)amine (TCTA), poly(4-butylphenyl-diphenylamine) (poly-TPD), poly(4-butylphenyl-diphenylamine) (α-NPD), 4,4′-cyclohexylidene-bis[N,N-bis(4-methylphenyl)benzenamine] (TAPC), 4,4′,4″-tris[2-naphthyl(phenyl)-amino]triphenylamine (2-TNATA), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN, and / or The HTL may also include star-shaped heterocycles such as 9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole (TrisPcz). The HTL may also include a p-doped layer consisting of an inorganic or organic dopant in an organic hole-transporting matrix. The inorganic dopants may be transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide. The organic dopants may be tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), copper-pentafluorobenzoate (Cu(I)pFBz) or transition metal complexes can be used.

[0103] EBLs may include, for example, 1,3-bis(carbazol-9-yl)benzene (mCP), TCTA, 2-TNATA, 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), tris-Pcz, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), and / or N,N'-dicarbazolyl-1,4-dimethylbenzene (DCB).

[0104] Adjacent to the hole transport layer (HTL) or (if present) the electron blocking layer (EBL) is typically the light emitting layer (EML). The light emitting layer (EML) contains at least one light emitting molecule (i.e., emitter material). The EML typically further contains one or more host materials (also called matrix materials). For example, the host material may be 4,4'-bis-(N-carbazolyl)-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), bis[2-(diphenylphosphino)phenyl]etheroxide (DPEPO), 9-[3-(dibenzofuran-2-yl)phenyl]-9H- carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T) and / or 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST). As known to those skilled in the art, host materials should generally be selected to exhibit a first (i.e., lowest) excited triplet state (T1) and a first (i.e., lowest) excited singlet state (S1) energy level that is higher in energy than the first (i.e., lowest) excited triplet state (T1) and the first (i.e., lowest) excited singlet state (S1) energy level of at least one emissive molecule incorporated into the respective host material.

[0105] As mentioned above, in the context of the present invention, it is preferred that at least one EML of an optoelectronic device comprises at least one molecule according to the invention. Preferred compositions of EMLs of optoelectronic devices comprising at least one organic molecule according to the invention are explained in more detail in the following sections of the text (see below).

[0106] Adjacent to the light-emitting layer (EML) may be an electron-transporting layer (ETL). Any electron transporter may be used here. Exemplarily, electron-deficient compounds such as benzimidazole, pyridine, triazole, triazine, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxides, and sulfones may be used. The electron transporter may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi). The ETL may be 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline) (Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,7-di(2,2'-bipyridin-5-yl)triphenyl (BPyTP2), dibenzo[b,d]thiophen-2-yltriphenylsilane (Sif87), dibenzo[b,d]thiophen-2-yl)diphenylsilane (Sif88), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) and / or 4,4'-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl (BTB). Optionally, the ETL is doped with a material such as 8-hydroxyquinolinolatolithium (Liq). The electron transport layer (ETL) can also block holes. Alternatively, a hole blocking layer (HBL) is typically introduced between the EML and the ETL.

[0107] The hole blocking layer (HBL) may be, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline=bathocuproine (BCP), 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 9,9'-(5-(6-([1,1'-biphenyl]-3-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum (BAlq), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), aluminum-tris(8-hydroxyquinoline)(Alq 3 ), diphenyl-4-triphenylsilylphenyl-phosphine oxide (TSPO1), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), 2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine (T3T), 2,4,6-tris(9,9'-spirobifluoren-2-yl)-1,3,5-triazine (TST) and / or 1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazol-9-yl)benzene (TCB / TCP).

[0108] Adjacent to the electron transport layer (ETL) may be a cathode layer C. The cathode layer C may, for example, comprise or consist of a metal (e.g. Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W or Pd) or a metal alloy. For practical reasons, the cathode layer C may also consist of an (essentially) opaque metal such as Mg, Ca or Al. Alternatively, or in addition, the cathode layer C may also comprise graphite and / or carbon nanotubes (CNTs). Alternatively, the cathode layer C may also comprise or consist of nanoscale silver wires.

[0109] The OLED may optionally further include a protective layer (also called an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer C. The layer may be any of lithium fluoride, cesium fluoride, silver, 8-hydroxyquinolinolatolithium (Liq), Li 2 O, BaF 2 , MgO and / or NaF.

[0110] Optionally, the electron transport layer (ETL) and / or the hole blocking layer (HBL) also comprise one or more host compounds.

[0111] As used herein, unless more specifically defined in a particular context, the hue designations of emitted and / or absorbed light are as follows: Purple: >380~420nm wavelength range Deep blue: wavelength range >420~480nm Sky blue: Wavelength range >480~500nm Green: >500~560nm wavelength range Yellow: >560~580nm wavelength range Orange: >580~620nm wavelength range Red: >620~800nm ​​wavelength range Associated with the emitter molecule, such hues exhibit maximum emission, so for example, a deep blue emitter has a maximum emission in the range >420-480 nm, a sky blue emitter has a maximum emission in the range >480-500 nm, a green emitter has a maximum emission in the range >500-560 nm, and a red emitter has a maximum emission in the range >620-800 nm.

[0112] The deep blue emitter may preferably have a maximum emission of less than 475 nm, more preferably less than 470 nm, even more preferably less than 465 nm, or even more preferably less than 460 nm. It is generally 420 nm or more, preferably 430 nm or more, more preferably 440 nm or more, or even more preferably 450 nm or more. In one embodiment, the organic molecules according to the invention generally exhibit a maximum emission of 420-500 nm, more preferably 430-490 nm, even more preferably 440-480 nm, and most preferably 450-470 nm, measured at room temperature (i.e. (about) 20° C.) from a spin-coated film containing 10% by weight of the organic molecules according to the invention in poly(methyl methacrylate) (PMMA).

[0113] Yet another embodiment relates to an OLED comprising at least one organic molecule according to the present invention and emitting light having CIEx and CIEy color coordinates close to the CIEx (=0.131) and CIEy (=0.046) color coordinates of primary blue (CIEx=0.131 and CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD (Ultra High Definition) displays, e.g. UHD-TV. Thus, a further aspect of the present invention relates to an OLED comprising one or more organic molecules according to the present invention, the emission of which exhibits a CIEx colour coordinate of 0.02 to 0.30, preferably 0.03 to 0.25, more preferably 0.05 to 0.20, even more preferably 0.08 to 0.18 or even more preferably 0.10 to 0.15 and / or a CIEy colour coordinate of 0.00 to 0.45, preferably 0.01 to 0.30, more preferably 0.02 to 0.20, even more preferably 0.03 to 0.15 or even more preferably 0.04 to 0.10.

[0114] Yet another embodiment has a luminance of 1000 cd / m 2and / or has an external quantum efficiency of 8% or more, preferably 10% or more, more preferably 13% or more, even more preferably more than 15%, or even more preferably more than 20%, and / or has a maximum emission of 420 nm to 500 nm, preferably 430 nm to 490 nm, more preferably 440 nm to 480 nm, and most preferably 450 nm to 470 nm, and / or has a maximum emission of 500 cd / m 2 The present invention relates to an OLED that exhibits an LT80 value of 100 hours or more, preferably 200 hours or more, more preferably 400 hours or more, even more preferably 750 hours or more, or even more preferably 1000 hours or more.

[0115] The green emitter material may preferably have an emission maximum of 500-560 nm, more preferably 510-550 nm, even more preferably 520-540 nm. In a preferred embodiment, the organic molecules according to the invention generally exhibit an emission maximum of 500-560 nm, more preferably 510-550 nm, most preferably 520-540 nm, measured at room temperature (i.e. (about) 20° C.) from a spin-coated film comprising 10% by weight of the organic molecules according to the invention in poly(methyl methacrylate) (PMMA).

[0116] Yet another embodiment relates to an OLED comprising at least one organic molecule according to the present invention and emitting light having CIEx and CIEy color coordinates close to the CIEx (=0.170) and CIEy (=0.797) color coordinates of primary green (CIEx=0.170 and CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), which is suitable for use in UHD displays, e.g., UHD-TV. The term "close" in this paragraph refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. While in commercial applications, a top light-emitting element (where the top electrode is transparent) is typically used, the test element used throughout the present invention refers to a bottom light-emitting element (where the bottom electrode and substrate are transparent). Thus, a further aspect of the present invention relates to an OLED whose emission exhibits a CIEx colour coordinate of 0.10 to 0.45, preferably 0.10 to 0.35, more preferably 0.10 to 0.30, even more preferably 0.10 to 0.25 or even more preferably 0.15 to 0.20, and / or a CIEy colour coordinate of 0.60 to 0.92, preferably 0.65 to 0.90, more preferably 0.70 to 0.88, even more preferably 0.75 to 0.86 or even more preferably 0.79 to 0.84.

[0117] Yet another preferred embodiment has a luminance of 14500 cd / m 2 and / or has an external quantum efficiency of more than 10%, preferably more than 13%, more preferably more than 15%, even more preferably more than 17%, or even more preferably more than 20%; and / or has a maximum emission of 500-560 nm, preferably 510-550 nm, more preferably 520-540 nm, and / or has a maximum emission of 14,500 cd / m 2 The present invention relates to an OLED that exhibits a LT97 value of 100 h or more, preferably 250 h or more, more preferably 500 h or more, even more preferably 750 h or more, or even more preferably 1000 h or more.

[0118] Yet another preferred embodiment concerns an OLED comprising one or more organic molecules according to the invention and emitting at a well-defined color point. Preferably, the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)). In a preferred embodiment, the OLED comprising at least one organic molecule according to the invention emits light with a FWHM of the main emission peak of less than 0.50 eV, preferably less than 0.48 eV, more preferably less than 0.45 eV, more preferably less than 0.43 eV, more preferably less than 0.40 eV, more preferably less than 0.35 eV, more preferably less than 0.30 eV, or more preferably less than 0.25 eV.

[0119] According to the present invention, optoelectronic devices comprising one or more organic molecules according to the present invention can be used, for example, as displays, light sources for lighting applications, and as light sources for medical and / or cosmetic applications (eg phototherapy).

[0120] Combination of organic molecules and additional substances according to the present invention It forms part of general knowledge for a person skilled in the art that any layer within an optoelectronic device, here preferably an OLED, in particular the light-emitting layer (EML), may consist of a single material or a combination of different materials.

[0121] For example, those skilled in the art will understand that an EML is composed of a single material that emits light when a voltage (and current) is applied to the device. However, those skilled in the art will appreciate that in the EML of an optoelectronic device (here, preferably an OLED), different materials may be present, in particular one or more host materials (i.e., matrix materials; here, when included in an optoelectronic device comprising at least one organic molecule according to the present invention, the host material H B It will be appreciated that it is advantageous to combine one or more dopant materials, at least one of which emits light (i.e., an emitter material), with one or more dopant materials, at least one of which emits light upon application of a voltage and current to the device.

[0122] In a preferred embodiment of the use of the organic molecules according to the invention in an optoelectronic device, said optoelectronic device comprises one or more organic molecules according to the invention in the EML, or in a layer directly adjacent to the EML, or in one or more of these layers.

[0123] In a preferred embodiment of the use of the organic molecules according to the invention in an optoelectronic device, said optoelectronic device is an OLED and comprises one or more organic molecules according to the invention in the EML, or in a layer directly adjacent to the EML, or in one or more of these layers.

[0124] In a more preferred embodiment of the use of the organic molecules according to the invention in an optoelectronic device, said optoelectronic device is an OLED, which comprises one or more organic molecules according to the invention in an EML. The skilled person will understand that this means that at least one organic molecule according to the invention is, for example, in the host material H of the respective EML. B (i.e., a matrix material), or at least one host material H B It is understood that the term "optoelectronic device" means that the dopant (material) can be used as an emissive (i.e., an emitter material) or non-emissive (i.e., does not emit light when a voltage and current is applied to the optoelectronic device).

[0125] In one embodiment of an optoelectronic device, preferably an OLED, comprising one or more organic molecules according to the invention, one or more, preferably each, organic molecule according to the invention is used as an emitter material in the emissive layer EML, i.e. it emits light when a voltage (and current) is applied across the device.

[0126] In another embodiment of an optoelectronic device, preferably an OLED, comprising one or more organic molecules according to the invention, the one or more, preferably each, organic molecule according to the invention is present in the emissive layer EML but does not emit light when a voltage (and current) is applied to the device, i.e. in that case the at least one organic molecule according to the invention is not a host material H Bor non-emissive dopants, both of which are known to those skilled in the art.

[0127] In one embodiment of an optoelectronic device, preferably an OLED, comprising one or more organic molecules according to the present invention, the one or more organic molecules according to the present invention are included in one or more EMLs. Those skilled in the art will appreciate that this means that the one or more organic molecules according to the present invention are either emitter materials (i.e., emissive dopant materials) in the EMLs or host materials H in the EMLs. B or both are non-emissive dopant materials in the EML, or the organic molecules are, independently of each other, a host material H B , is understood to mean selected from emitter materials (i.e., luminescent dopant materials) or non-luminescent dopant materials.

[0128] As known to those skilled in the art, for example, in an organic light emitting diode (OLED), emission from an emitter material (i.e., an emissive dopant) includes fluorescence from an excited singlet state (generally the lowest excited singlet state S1) and phosphorescence from an excited triplet state (generally the lowest excited triplet state T1).

[0129] Fluorescent emitter F can emit light at room temperature (i.e., (about) 20° C.) upon electronic excitation (e.g., in an optoelectronic device), and the emissive excited state is a singlet state. Fluorescent emitters generally exhibit immediate (i.e., direct) fluorescence on the nanosecond time scale when initial electronic excitation (e.g., by electron-hole recombination) provides an excited singlet state of the emitter.

[0130] In the context of the present invention, a delayed fluorescent material is a material that can reach an excited triplet state (generally the lowest excited triplet state T1) to an excited singlet state (generally the lowest excited singlet state S1) by reverse intersystem crossing (RISC; i.e., up-intersystem crossing or reverse intersystem crossing) and can emit light when returning from the excited singlet state (generally S1) thus reached to the electronic ground state. The time scale (generally in the microsecond range) at which the observed fluorescence emission occurs after RISC from an excited triplet state (generally T1) to an excited singlet state (generally S1) is slower than the time scale (generally in the nanosecond range) at which direct (i.e., immediate) fluorescence occurs, and is therefore referred to as delayed fluorescence (DF). When RISC from an excited triplet state (generally from T1) to an excited singlet state (generally to S1) occurs via thermal activation and the excited singlet state thus filled emits light (delayed fluorescence emission), the process is referred to as thermally activated delayed fluorescence (TADF). Therefore, a TADF material is a material that can emit thermally activated delayed fluorescence (TADF) as described above. The lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ) and the energy difference ΔE ST It is known to those skilled in the art that the switching from the lowest excited singlet state to the lowest excited triplet state by RISC occurs with high efficiency if ΔE ST It forms part of the general knowledge of the person skilled in the art that TADF materials have a value (see below). As known to the person skilled in the art, a TADF material is not simply a material capable of RISC on its own from an excited triplet state to an excited singlet state with subsequent emission of TADF as described above. A TADF material is in fact a material that is composed of two types of materials, preferably two host materials H B More preferably, the p-host material H P and n-host material H N It is known to those skilled in the art that the exciplex formed is (see below).

[0131] The (thermally activated) delayed fluorescence evolution is analyzed, for example, based on decay curves obtained from time-resolved (i.e., transient) photoluminescence (PL) measurements. For this, spin-coated films of 1-10 wt. %, in particular 10 wt. %, of each emitter (i.e., the assumed TADF material) in poly(methyl methacrylate) (PMMA) are used as samples. The analysis is performed, for example, using an FS5 fluorescence spectrometer from Edinburgh Instruments. A nitrogen atmosphere is maintained while the sample PMMA film is placed in a cuvette and measured. Data collection is performed using the well-established Time Correlated Single Photon Counting (TCSPC, see below) technique. Measurements can be performed and combined in four time domains (200 ns, 1 μs, 20 μs and even longer measurement periods of >80 μs) in order to collect the entire decay dynamics over several orders of magnitude in time and signal intensity (see below).

[0132] The TADF material preferably satisfies the following two conditions in relation to the overall damping dynamics mentioned above: (i) the damping dynamics exhibit two time domains, one in the nanosecond (ns) range and the other in the microsecond (μs) range; and (ii) The emission spectral morphology is consistent in the two time domains. Here, the portion of the light emitted in the first decay region is taken as immediate fluorescence, and the portion of the light emitted in the second decay region is taken as delayed fluorescence. The ratio of delayed to immediate fluorescence is expressed in the form of the so-called n-value, which is calculated by integrating the respective photoluminescence decays over time according to the following equation:

number

[0133] In the context of the present invention, TADF materials preferably have an n>0.05, more preferably an n>0.1, even more preferably an n>0.15, particularly preferably an n>0.15, particularly preferably an n>0.20, or even more preferably an n>0.25.

[0134] In a preferred embodiment, the organic molecules according to the invention exhibit an n value (ratio of delayed to immediate fluorescence) greater than 0.05 (n>0.05).

[0135] In the context of the present invention, the TADF material E B is the lowest excited singlet state energy level E(S1 E ) and the lowest excited triplet state energy level E(T1 E ) corresponds to the energy difference ΔE ST The TADF material E is characterized by exhibiting a value of less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, or even more preferably less than 0.05 eV. B ΔE ST The method for determining the value is explained later in this text.

[0136] In a preferred embodiment, the organic molecule according to the present invention is a TADF material E as defined herein. B and ΔE corresponds to the energy difference between the lowest excited singlet state energy level and the lowest excited triplet state energy level. ST values ​​of less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.13 eV, or even more preferably less than 0.07 eV. In the paragraph on compositions comprising at least one organic molecule according to the invention (see below), one or more TADF substances E different from the organic molecule according to the invention may be B The skilled artisan will recognize that any TADF material disclosed in the state of the art is a suitable TADF material in this context. BThose skilled in the art will also understand that the TADF material E B However, it is understood that TADF materials are generally designed so that the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) are largely spatially separated by the (electron) donor group and (electron) acceptor group, respectively. The groups are generally bulky (i.e., sterically required) or are twisted by being bonded via a spiro junction, reducing the spatial overlap of the HOMO and LUMO. However, minimizing the spatial overlap of the HOMO and LUMO has the disadvantage that the photoluminescence quantum yield (PLQY) of the TADF material is also reduced. Therefore, in practice, taking into account both of these two effects, ΔE ST and achieve a high PLQY.

[0137] One common approach for TADF material design is to covalently link one or more HOMO-distributed (electron) donor moieties and one or more LUMO-distributed (electron) acceptor moieties to the same bridge, referred to herein as a linker group. B may, for example, contain two or three linker groups attached to the same acceptor moiety, and additional donor and acceptor moieties may be attached to each of the two or three linker groups.

[0138] Also, one or more donor moieties and one or more acceptor moieties can be directly attached to one another (without the presence of a linker group).

[0139] Typical donor moieties are derivatives of diphenylamine, indole, carbazole, acridine, phenoxazine and related structures. In particular, aliphatic, aromatic or heteroaromatic ring systems can be condensed to the aforementioned donor precursors to reach, for example, indolocarbazoles.

[0140] Derivatives of benzene, biphenyl, and to some extent terphenyl, are common linker groups.

[0141] Nitrile groups are very common acceptor moieties in TADF materials, well-known examples of which include: (i) Carbazolyldicyanobenzene compounds 2CzPN (4,5-di(9H-carbazol-9-yl)phthalonitrile), DCzIPN (4,6-di(9H-carbazol-9-yl)isophthalonitrile), 4CzPN (3,4,5,6-tetra(9H-carbazol-9-yl)phthalonitrile), 4CzIPN (2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile), 4CzTPN (2,4,5,6-tetra(9H-carbazol-9-yl)terephthalonitrile) and their derivatives, (ii) Carbazolylcyanopyridine compounds 4CzCNPy (2,3,5,6-tetra(9H-carbazol-9-yl)-4-cyanopyridine) and its derivatives, (iii) Carbazolylcyanobiphenyl compounds CNBPCz (4,4',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2'-dicarbonitrile), CzBPCN (4,4',6,6'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-3,3'-dicarbonitrile), DDCzIPN (3,3',5,5'-tetra(9H-carbazol-9-yl)-[1,1'-biphenyl]-2,2',6,6'-tetracarbonitrile) and their derivatives, wherein in these materials one or more of the nitrile groups is substituted with fluorine (F) or trifluoromethyl (CF 3 ) can also be substituted. Nitrogen heterocycles such as triazine, pyrimidine, triazole, oxadiazole, thiadiazole, heptazine, 1,4-diazatriphenylene, benzothiazole, benzoxazole, quinoxaline, and diazafluorene derivatives are also well-known acceptor moieties used in TADF molecular constructions. For example, known examples of TADF molecules containing triazine acceptors include PIC-TRZ (7,7'-(6-([1,1'-biphenyl]-4-yl)-1,3,5-triazine-2,4-diyl)bis(5-phenyl-5,7-dihydroindolo[2,3-b]carbazole)), mBFCzTrz (5-(3-(4,6-diphenyl-1,3,5-triazin-2-yl))phenyl)-5H-benzofuro[3,2-c]carbazole), and DCzTrz (9,9'-(5-(4,6-diphenyl-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole)). Another group of TADF materials includes diaryl ketones such as benzophenone or (heteroaryl)aryl ketones such as 4-benzoylpyridine, 9,10-anthraquinone, 9H-xanthen-9-one and their derivatives as acceptor moieties to which donor moieties (mainly carbazolyl substituents) are attached. Examples of such TADF molecules include BPBCz (bis(4-(9'-phenyl-9H,9'H-[3,3'-bicarbazol]-9-yl)phenyl)methanone), mDCBP ((3,5-di(9H-carbazol-9-yl)phenyl)(pyridin-4-yl)methanone), AQ-DTBu-Cz (2,6-bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)anthracene-9,10-dione), and MCz-XT (3-(1,3,6,8-tetramethyl-9H-carbazol-9-yl)-9H-xanthen-9-one), respectively. Sulfoxides, particularly diphenyl sulfoxides, are also commonly used as acceptor moieties for the construction of TADF materials; well-known examples include 4-PC-DPS (9-phenyl-3-(4-(phenylsulfonyl)phenyl)-9H-carbazole), DitBu-DPS (9,9'-(sulfonylbis(4,1-phenylene))bis(9H-carbazole)), and TXO-PhCz (2-(9-phenyl-9H-carbazol-3-yl)-9H-thioxanthen-9-one 10,10-dioxide).

[0142] The fluorescent emitter F may also exhibit a TADF as defined herein, and more preferably a TADF material E as defined herein. B As a result, the small FWHM emitter S as defined herein is understood to be B is the TADF material E as defined herein B It may or may not be so.

[0143] Phosphorescence, i.e., emission from an excited triplet state (typically the lowest excited triplet state T1), is a spin-forbidden process. As known to those skilled in the art, phosphorescence can be enhanced by utilizing (intramolecular) spin-orbit interactions (the so-called (internal) heavy atom effect). In the context of the present invention, the phosphorescent material P B is a phosphorescent emitter capable of emitting phosphorescence at room temperature (i.e., (approximately) 20° C.).

[0144] Here, the phosphorescent material P B It is preferred that the phosphor P contains at least one atom of an element having a nominal atomic weight greater than that of calcium (Ca). More preferably, in the context of the present invention, the phosphor P B contains transition metal atoms, particularly transition metal atoms of elements having a standard atomic weight greater than that of zinc (Zn). B The transition metal atoms preferably present in exist in any oxidation state (and can also exist as ions of the respective elements).

[0145] Phosphorescent material P used in organic electroluminescence devices B It is common knowledge for a person skilled in the art that the phosphorescent material P is Ir, Pd, Pt, Au, Os, Eu, Ru, Re, Ag and Cu, preferably Ir, Pt and Pd in ​​the context of the present invention, more preferably a complex of Ir and Pt. A person skilled in the art will understand what material is phosphorescent material P in optoelectronic devices. B Those skilled in the art are also familiar with the principles of designing phosphorescent complexes for use as phosphorescent materials in optoelectronic devices and know how to tune the emission of the complexes through structural variations.

[0146] Those skilled in the art will recognize that the phosphorescent material P used in optoelectronic devices B In this connection, the skilled artisan will be aware of what materials are suitable as phosphorescent materials P and how to synthesize them. B The principles of designing phosphorescent complexes for use as photocatalysts are well understood and methods for tuning the emission of the complexes through structural changes are known.

[0147] Phosphorescent substances P that can be used with the organic molecules according to the invention B Non-limiting examples of (for example in the form of compositions or in the EML of optoelectronic devices, see below) are disclosed in the state of the art. For example, the following metal complexes can be used as phosphorescent materials P that can be used with the organic molecules according to the invention: B Is: [ka]

[0148] In the context of the present invention, a small full width at half maximum (FWHM) emitter S Bis any emitter (i.e., emitter material) having an emission spectrum exhibiting a FWHM of 0.35 eV or less (≦0.35 eV), preferably 0.30 eV or less (≦0.30 eV), especially 0.25 eV or less (≦0.25 eV). Unless otherwise specified, this is determined based on the emission spectrum of each emitter at room temperature (i.e., (about) 20° C.), typically measured at 1-5 wt %, especially 2 wt %, of the emitter weight in poly(methyl methacrylate) (PMMA). Alternatively, a small FWHM emitter S B The emission spectra of the emitters S are typically measured at room temperature (i.e., (approximately) 20 °C) in dichloromethane or toluene at 0.001–0.2 mg / mL. B can be measured in a solution.

[0149] Small FWHM emitter S B are fluorescent emitters F, phosphorescent emitters (e.g., phosphorescent materials P B ) and / or TADF emitters (e.g., TADF material E B The organic molecule according to the present invention, the aforementioned TADF material E B and phosphorescent material P B In the case of B or P B are recorded from each of the spin-coated films.

[0150] As known to those skilled in the art, the emitter (e.g., a small FWHM emitter S B The full width at half maximum (FWHM) of the emission spectrum (fluorescence spectrum for fluorescent emitters and phosphorescence spectrum for phosphorescent emitters) is easily determined from the respective emission spectrum (fluorescence spectrum for fluorescent emitters and phosphorescence spectrum for phosphorescent emitters). All reported FWHM values ​​generally refer to the main emission peak (i.e., the peak with the highest intensity). Means of determining the FWHM (here preferably reported in electron volts, eV) are part of the common knowledge of the skilled artisan. For example, if the main emission peak of an emission spectrum is found to be between two wavelengths λ taken in nanometers (nm) from the emission spectrum, then the FWHM can be calculated by multiplying the FWHM by 100%. 1 and λ 2When half the maximum emission is reached (i.e., 50% of the maximum emission intensity) at , the FWHM in electron volts (eV) is typically determined using the following equation:

number

[0151] In the context of the present invention, a small FWHM emitter S B is an organic emitter, which in the context of the present invention means that it does not contain any transition metal. Preferably, in the context of the present invention, a small FWHM emitter S B is composed primarily of the elements hydrogen (H), carbon (C), nitrogen (N) and boron (B), but can also contain, for example, oxygen (O), silicon (Si), fluorine (F) and bromine (Br).

[0152] Also, in the context of the present invention, a small FWHM emitter S B is preferably a fluorescent emitter F which may or may not further exhibit TADF.

[0153] Preferably, in the context of the present invention, a small FWHM emitter S B meets at least one of the following requirements: (i) Boron (B)-containing emitters, which have the respective small FWHM emitters S B At least one atom in the (ii) contain a polycyclic aromatic or heteroaromatic core structure, where at least two aromatic rings are fused together (eg, anthracene, pyrene or aza derivatives thereof). More preferably, in the context of the present invention, a small FWHM emitter S B meets at least one of the following requirements: (i) Boron (B)-containing emitters, which have the respective small FWHM emitters S B At least one atom in the (ii) Contains a pyrene core structure. Most preferably, in the context of the present invention, a small FWHM emitter S B are boron (B)-containing emitters, which are the small FWHM emitters S B This means that at least one atom in is boron (B). Those skilled in the art will recognize that a small FWHM emitter S that meets the aforementioned requirements or preferred characteristics may be B We know how to design. In the context of the present invention, a small FWHM emitter S B A class of fluorescent emitters F suitable as are the well-known 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) based materials, whose structural features and applications in optoelectronic devices have been discussed in detail and are common knowledge to those skilled in the art. The state of the art also shows how such materials can be synthesized and how to arrive at emitters with specific emission hues.

[0154] Those skilled in the art will also recognize that the BODIPY basic structure shown below is [ka] For example, they are well aware that intermolecular π-π interactions and the associated self-quenching make them less than ideally suited as emitters in optoelectronic devices.

[0155] Alternative emitter materials for optoelectronic devices have bulky (i.e., sterically demanding) groups as substituents attached to the aforementioned BODIPY core structure. Such bulky groups can be, for example, aryl, heteroaryl, alkyl or alkoxy substituents (among many others) or fused polyaromatic or heteroaromatic groups, any of which may be optionally substituted. The selection of suitable substituents on the BODIPY core will be apparent to one skilled in the art and can be readily derived from the state of the art, as well as the numerous synthetic routes that have been established for the synthesis and subsequent modification of such molecules.

[0156] In the context of the present invention, a small FWHM emitter S B Examples of suitable BODIPY emitters are shown below: [ka] [ka] [ka] [ka]

[0157] In addition, one or both of the fluorine substituents attached to the central boron atom of the BODIPY core structure may be attached via an oxygen atom, preferably fluorine (F) or trifluoromethyl (CF 3 It is known to those skilled in the art that by substituting alkoxy or aryloxy groups selectively substituted with electron-withdrawing substituents such as aryloxy, ... B does not mean: [ka]

[0158] Those skilled in the art will appreciate that virtually all BODIPY-based emitters and their derivatives used in the state of the art, e.g. as fluorescent emitters F, have a particularly small FWHM emitter S B It is understood that any of the above may be used with the organic molecules according to the present invention.

[0159] In the context of the present invention, a small FWHM emitter S BAnother class of molecules suitable for providing a charge-transfer (Pt) emitter are near-range-charge-transfer (NRCT) emitters.

[0160] Typical NRCT emitters have been described in the literature as exhibiting a delayed component in the time-resolved photoluminescence spectrum, indicating short-range HOMO-LUMO separation.

[0161] A typical NRCT emitter exhibits only one emission band in the emission spectrum, whereas a typical fluorescent emitter exhibits multiple unique emission bands due to vibrational progression.

[0162] Those skilled in the art will appreciate that a small FWHM emitter S in the context of the present invention B It is now known how to design and synthesize suitable NRCT emitters.

[0163] A small FWHM emitter S as defined herein B and additional fluorescent emitters F (see below) that can be used with the organic molecules according to the invention are boron-containing emitters as shown below: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] Here, this means that only the materials shown are small FWHM emitters S in the context of the present invention. B It is not meant to be used as a

[0164] Small FWHM emitter S B Another group of fluorescent emitters F that can be used as small FWHM emitters S in the context of the present invention are boron-containing emitters that contain exactly one direct BN bond. B It is understood that the small FWHM emitter S B A non-limiting example is a boron-containing emitter that contains exactly one direct BN bond that includes or consists of the following structure: [ka] The structures may be further substituted, and the structural units and / or substituents may be linked to form fused ring systems.

[0165] Small FWHM emitter S B Specific non-limiting examples of emitters that can be used are: [ka]

[0166] One approach to designing fluorescent emitters F relies on the use of fluorescent polycyclic aromatic or heteroaromatic core structures. The latter, in the context of the present invention, is any structure comprising one or more aromatic or heteroaromatic rings, preferably two or more of said rings, which are more preferably fused to each other or linked via one or more direct bonds or bond atoms. That is, the fluorescent core structure comprises at least one, and preferably only one, rigid conjugated π-system.

[0167] A person skilled in the art knows how to select a fluorescent core structure for a fluorescent emitter F. Non-limiting examples of common fluorescent core structures for fluorescent emitters F are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0168] In the present context, the term "fluorescent core structure" indicates that any molecule comprising said core can potentially be used as a fluorescent emitter F. The skilled artisan will know that the core structure of such a fluorescent emitter F may be optionally substituted and what substituents are suitable in connection therewith.

[0169] As known to those skilled in the art, the host material H of the EML B is a host material H that can transport electrons or positive charges through the EML. B Those skilled in the art will appreciate that the host material H contained in the EML of an optoelectronic device (e.g., an OLED) can transfer excitation energy to at least one emitter material doped in the EML. B Those skilled in the art will also appreciate that any host material H generally does not significantly contribute to the emission of light from the device upon application of voltage and current. B However, the p-host H P , n-host H showing high electron mobility N or an ambipolar host material H that exhibits both high hole mobility and high electron mobility BP It is known for a fact that.

[0170] As known to those skilled in the art, the EML also contains at least one p-host H P and one n-host H N In particular, the EML comprises exactly one emitter material according to the invention and a n-host H N 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T) as p-host H PThe present invention also includes a mixed host system comprising a host selected from CBP, mCP, mCBP, 4,6-diphenyl-2-(3-(triphenylsilyl)phenyl)-1,3,5-triazine, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0171] The EML contains at least one p-host H P and one n-host H N This includes so-called mixed host systems, where there are n-hosts H N contains groups derived from pyridine, pyrimidine, benzopyrimidine, 1,3,5-triazine, 1,2,4-triazine and 1,2,3-triazine, and the p-host H P includes radicals derived from indole, isoindole and preferably carbazole.

[0172] A person skilled in the art knows what materials are suitable host materials for use in organic electroluminescent devices. Any host material used in the state of the art is considered a suitable host material H in the context of the present invention. B It is understood that

[0173] In the context of the present invention, the p-host material H P Substance H B Non-limiting examples are listed below: [ka] [ka] [ka] [ka] [ka] [ka]

[0174] In the context of the present invention, the n-host material H N Substance H B Non-limiting examples are listed below: [ka] [ka] [ka]

[0175] Those skilled in the art will appreciate that any materials contained in the same layer, particularly the same EML, as well as materials in adjacent layers that are in close proximity at the interface between those adjacent layers, can form exciplexes together. Those skilled in the art will appreciate that exciplex-forming material pairs, particularly p-host H P and n-host H N It is known how to select pairs of materials, as well as selection criteria for the two components of the material pair, including HOMO and / or LUMO energy requirements. That is, when exciplex formation is desired, one component, e.g., the p-host material H P The HOMO of the n-host material H N The HOMO of the host material H is at least 0.20 eV higher in energy than the HOMO of the host material H. P The LUMO of the n-host material H NThe exciplex has an energy at least 0.20 eV higher than the LUMO of the exciplex. It is common knowledge for those skilled in the art that if an exciplex is present in the EML of an optoelectronic device, especially an OLED, the exciplex has the function of an emitter material and can emit light when a voltage and a current are applied to the device. As is known from the state of the art and generally, an exciplex can also be non-emissive and, for example, when it is included in the EML of an optoelectronic device, it can transfer excitation energy to a light-emitting material.

[0176] Compositions Comprising One or More Organic Molecules According to the Invention An aspect of the present invention relates to a composition comprising one or more organic molecules according to the present invention. An aspect of the present invention relates to the use of said composition in an optoelectronic device, preferably an OLED, in particular in the EML of said device.

[0177] Hereinafter, when describing the above compositions, the content of a specific substance in each composition may be referred to in the form of a percentage. It should be noted that unless otherwise specified in a particular embodiment, all percentages refer to weight percentages, which have the same meaning as weight percentages or weight % ((weight / weight), (w / w), weight %). For example, when the content of one or more organic molecules according to the present invention is illustratively referred to as 30% in a particular composition, this is understood to mean that the total weight of one or more organic molecules according to the present invention (i.e., all of those molecules combined) is 30% by weight, i.e., 30% of the total weight of the respective composition. By providing the preferred content of a component in weight %, it is understood that each time a composition is specified, the total content of all components adds up to 100% by weight (i.e., the total weight of the composition).

[0178] In the following description of embodiments of the invention relating to compositions comprising at least one organic molecule according to the invention, reference will be made to energy transfer processes occurring between components in the compositions when they are used in an optoelectronic device, preferably in the EML of an optoelectronic device, most preferably in the EML of an OLED. Those skilled in the art will appreciate that such excitation energy transfer processes can improve the luminous efficiency when the compositions are used in the EML of an optoelectronic device.

[0179] Those skilled in the art will understand that, for the excitation energy transfer to occur (efficiently), there is preferably a spectral overlap between the emission spectrum of the energy donor and the absorption spectrum of the energy acceptor. Those skilled in the art will also understand that the intended energy donor must have a higher excited state energy level than the intended energy acceptor, i.e., the energy level E(S1)(donor) of the lowest excited singlet state S1(donor) of the energy donor and / or the energy level E(T1)(donor) of the lowest excited triplet state T1(donor) of the energy donor is preferably higher in energy than the energy level E(S1)(acceptor) of the lowest excited singlet state S1(acceptor) of the energy acceptor and / or the energy level E(T1)(acceptor) of the lowest excited triplet state T1(acceptor) of the energy acceptor. The selection of a substance that satisfies the above-mentioned preferred criteria can be easily achieved based on the standard knowledge of those skilled in the art without the inventive step. Experimental details on how to determine excited state energies and how to record absorption and emission spectra are provided later in the text.

[0180] When describing a composition comprising at least one organic molecule according to the present invention, it will also be noted that certain substances are "different" from other substances, meaning that substances that are "different" from one another do not have identical chemical structures.

[0181] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) optionally, one or more host substances H different from the organic molecules of (a); B , (c) one or more TADF substances E that are selectively different from the organic molecules of (a); B , (d) selectively, one or more phosphorescent substances P different from the organic molecules of (a); B , (e) a TADF material E selectively different from the organic molecule of (a) and (c); B one or more fluorescent emitters F different from (f) optionally one or more solvents and / or dyes; wherein any of the substances (a) to (e) (substances of the same group as defined above and / or substances of different groups as defined above) selectively form one or more exciplexes; wherein at least one of the substances (a) and / or (c) and / or (d), and / or at least one exciplex, is an emitter substance if the fluorescent emitter F of (e) is absent from the composition.

[0182] One or more organic molecules according to the invention and (optionally) one or more host materials H B A composition comprising One embodiment of the composition according to the invention comprises one or more organic molecules according to the invention and, optionally, one or more host substances H structurally different from the molecules of the invention. B The present invention relates to a composition comprising:

[0183] Preferably, at least one, and preferably each, emitter material of said compositions emits light with an emission maximum of >500-560 nm, more preferably 510-550 nm, even more preferably 520-540 nm in an emission spectrum recorded from a spin-coated film of 10 wt. % of each emitter in poly(methyl methacrylate) (PMMA) at room temperature (i.e. (about) 20° C.). If present, at least one, and preferably each, host material H Bis at least one, preferably the lowest excited singlet state S1 (H B When present, at least one, and preferably each, host material H B is preferably capable of transferring excitation energy to at least one, preferably each, emitter substance. The excitation energy can also be transferred between different organic molecules according to the invention, where it is particularly preferred that the excitation energy is transferred to at least one, preferably each, emitter substance.

[0184] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) one or more host substances H different from the organic molecules of (a) B , and (c) optionally one or more solvents.

[0185] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention, and (b) one or more host substances H different from the organic molecules of (a) B , Here, the host material H in the composition B is higher than the fraction (wt. %) of the organic molecules according to the invention, and preferably the fraction (wt. %) of the host material H in the composition B is twice as high as the fraction (% by weight) of the organic molecules according to the invention.

[0186] In one embodiment, the composition comprises or consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 5 to 99% by weight, preferably 30 to 95% by weight, in particular 40 to 90% by weight, of one or more host substances H different from the organic molecules of (a). B , and (c) 0 to 94% by weight, preferably 0 to 65% by weight, in particular 0 to 50% by weight, of one or more solvents, Here, materials in groups (a)-(c) add up to 100% by weight in certain embodiments.

[0187] A composition comprising at least one organic molecule according to the invention together with at least one (additional) fluorescent emitter F. A preferred embodiment of the composition relates to a composition comprising at least one organic molecule according to the invention, wherein at least one fluorescent emitter F (as defined above) is not a molecule of the invention (i.e. the organic molecule according to the invention is the fluorescent emitter and an additional fluorescent emitter F can be present in the composition).

[0188] In this case, any organic molecule according to the invention and at least one (additional) fluorescent emitter F can play the role of an emitter material, but preferably, when used in the EML of an optoelectronic device, the emission from the composition is mainly (i.e. more than 50%, preferably more than 60%, more preferably more than 70%, even more preferably more than 80% or even more preferably more than 90%) attributable to at least one, preferably exactly one, (additional) fluorescent emitter F, which is structurally different from the molecule of the invention. Furthermore, the excitation energy is preferably differentiated between the different materials in the composition, in particular between at least one, preferably each host material H B At least one, preferably each, TADF material E B and to at least one, preferably each (additional) fluorescent emitter F substance. The excitation energy is also preferably transferred between substances in the composition selected from: at least one organic molecule according to the invention and at least one (additional) fluorescent emitter F, in particular from at least one, preferably each organic molecule according to the invention to at least one, preferably each (additional) fluorescent emitter F. At least one, preferably each (additional) fluorescent emitter F is dissolved in a solvent at room temperature (i.e. (approximately) 20° C.) at 1-5% by weight, preferably 2% by weight, of each S in poly(methyl methacrylate) (PMMA). BA small FWHM emitter S in the context of the present invention emits green light with an emission maximum of >500-560 nm, more preferably 510 nm-550 nm, even more preferably 520-540 nm in the recorded emission spectrum from a spin-coated film of B It is particularly preferred that:

[0189] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) optionally, one or more host substances H different from the organic molecules of (a); B , (c) one or more fluorescent emitters F different from the organic molecules of (a), and (d) optionally one or more solvents; wherein at least one, preferably each, fluorescent emitter F of group (c) is present at room temperature (i.e. (approximately) 20° C.) in poly(methyl methacrylate) (PMMA) at 1-5 wt. %, preferably 2 wt. %, of each S B A small FWHM emitter S in the context of the present invention preferably emits green light with an emission maximum of >500-560 nm, more preferably 510-550 nm, even more preferably 520-540 nm in the recorded emission spectrum from a spin-coated film of B It is.

[0190] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention, and (c) one or more fluorescent emitters F different from the organic molecules of (a); Here, the fraction (wt %) of the organic molecules of group (a) is higher than the fraction (wt %) of the fluorescent emitter F of group (c), preferably the fraction (wt %) of the organic molecules of group (a) is at least 5 times higher than the fraction (wt %) of the fluorescent emitter F of group (c).

[0191] In one embodiment, the composition comprises or consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 30 to 98.9% by weight, preferably 48 to 94.5% by weight, in particular 65 to 89% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, in particular 1 to 5% by weight, of one or more (additional) fluorescent emitters F different from the organic molecules of (a), and (d) optionally 0 to 68.9% by weight, preferably 0 to 46.5% by weight, in particular 0 to 24% by weight, of one or more solvents, wherein at least one, preferably each, fluorescent emitter F of (c) is present at room temperature (i.e. (about) 20° C.) in poly(methyl methacrylate) (PMMA) at 1-5 wt %, preferably 2 wt %, of each S B A small FWHM emitter S in the context of the present invention preferably emits green light with an emission maximum of >500-560 nm, more preferably 510-550 nm, even more preferably 520-540 nm in the recorded emission spectrum from a spin-coated film of B and Here, in certain embodiments, the total weight of materials in groups (a)-(d) is 100% by weight.

[0192] At least one (additional) TADF substance E B and at least one organic molecule according to the present invention. Another preferred embodiment of the composition comprises at least one organic molecule according to the invention and at least one TADF substance E that is not a molecule of the invention, i.e. structurally different. B (as defined above).

[0193] In this case, at least one organic molecule according to the invention and at least one TADF substance E B Any material selected from the group can act as an emitter material. Furthermore, the excitation energy can be transmitted between different materials in the composition, in particular between at least one, and preferably each, of the host materials HB From at least one, preferably each TADF material E B and / or to at least one, preferably each, organic molecule according to the invention. The excitation energy is also transferred to at least one organic molecule according to the invention and to at least one TADF material E B It is particularly preferred to transfer at least one, preferably each emitter material, between the substances in the composition selected from one or more organic molecules according to the invention and one or more TADF substances E acting as emitter substances emitting green light with an emission maximum of >500-560 nm, more preferably 510-550 nm, even more preferably 520-540 nm in the emission spectrum recorded at room temperature (i.e. (approximately) 20° C.) from a spin-coated film of 10 wt. % emitter in poly(methyl methacrylate) (PMMA). B One or more substances selected from the following are preferred:

[0194] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) optionally, one or more host substances H different from the organic molecules of (a); B , (c) one or more TADF substances E different from the organic molecules of (a); B , and (d) optionally one or more solvents.

[0195] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention, and (c) one or more TADF substances E different from the organic molecules of (a); B , Here, TADF material E of group (c) B The fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the TADF material E of group (c). B is at least two times higher than the fraction (wt %) of the organic molecules of group (a).

[0196] In one embodiment, the composition comprises or consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.9% by weight, preferably 20 to 94.5% by weight, in particular 40 to 89% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.1 to 50% by weight, preferably 0.5 to 40% by weight, in particular 1 to 30% by weight of one or more TADF substances E different from the organic molecules of (a). B , and (d) 0 to 98.9% by weight, preferably 20 to 74.5% by weight, in particular 30 to 49% by weight, of one or more solvents, wherein at least one of (a) and / or (c) is an emitter material; In certain embodiments, the total weight of materials from groups (a)-(c) is 100% by weight.

[0197] At least one (additional) TADF substance E B and a composition comprising at least one organic molecule according to the invention together with at least one (additional) fluorescent emitter F. Yet another preferred embodiment of the composition comprises one or more organic molecules according to the invention, one or more TADF substances E which are not organic molecules according to the invention. B (as defined above) and one or more (additional) fluorescent emitters F (as defined above) which are not molecules of the invention.

[0198] In this case, at least one organic molecule according to the invention, at least one (additional) TADF substance E BAny substance selected from and at least one (additional) fluorescent emitter F can perform the role of an emitter substance. However, preferably, when used in an EML of an optoelectronic device, the emission from the composition is mainly (i.e., 50% or more, preferably 60% or more, more preferably 70% or more, even more preferably 80% or more, or even more preferably 90% or more) attributable to at least one, preferably exactly one (additional) fluorescent emitter F which is not a molecule of the invention. At least one, preferably each (additional) fluorescent emitter F is preferably present in a concentration of 1-5% by weight, preferably 2% by weight, of each S in poly(methyl methacrylate) (PMMA) at room temperature (i.e., (about) 20° C.). B A small FWHM emitter S in the context of the present invention emits green light with an emission maximum of >500-560 nm, more preferably 510 nm-550 nm, even more preferably 520-540 nm in the recorded emission spectrum from a spin-coated film of B It is particularly preferred that the excitation energy is preferably different between the different substances in the composition, in particular between at least one, preferably each, of the host substances H B At least one, preferably each, TADF material E B and to at least one, preferably each, (additional) fluorescent emitter substance F. The excitation energy is also preferably transferred between substances in the composition selected from: at least one organic molecule according to the invention, at least one (additional) TADF substance E B and at least one (additional) fluorescent emitter F, in particular at least one, preferably each organic molecule according to the invention and / or at least one, preferably each (additional) TADF substance E B to at least one, and preferably each, (additional) fluorescent emitter F.

[0199] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) optionally, one or more host substances H different from the organic molecules of (a); B , (c) one or more (additional) TADF substances E different from the organic molecules of (a); B , (d) The TADF material E in (c) is different from the organic molecule in (a). B one or more (additional) fluorescent emitters F different from (e) optionally one or more solvents; wherein at least one, preferably each, fluorescent emitter F of (d) is present at room temperature (i.e. (about) 20° C.) in poly(methyl methacrylate) (PMMA) at 1-5 wt %, preferably 2 wt %, of each S B A small FWHM emitter S in the context of the present invention emits green light with an emission maximum of >500-560 nm, more preferably 510-550 nm, even more preferably 520-540 nm in the recorded emission spectrum from a spin-coated film of B It is.

[0200] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (c) one or more TADF substances E different from the organic molecules of (a); B , and (d) The TADF material E in (c) is different from the organic molecule in (a). B one or more fluorescent emitters F distinct from Here, TADF material E of group (c) B The fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the TADF material E of group (c). B is at least two times higher than the fraction (wt. %) of the organic molecules of group (a); Here, the fraction (wt %) of the organic molecules of group (a) is higher than the fraction (wt %) of the fluorescent emitter F of group (d), and preferably, the fraction (wt %) of the organic molecules of group (a) is at least two times higher than the fraction (wt %) of the fluorescent emitter F of group (d).

[0201] In one embodiment, the composition comprises or consists of: (a) 1 to 50% by weight, preferably 5 to 40% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.8% by weight, preferably 0 to 94% by weight, in particular 0 to 88% by weight, of one or more host substances H different from the organic molecules of (a). B , (c) 0.1 to 98.9% by weight, preferably 0.5 to 94.5% by weight, in particular 1 to 89% by weight, of one or more TADF substances E different from the organic molecules of (a). B , (d) 0.1 to 20 wt. %, preferably 0.5 to 12 wt. %, in particular 1 to 5 wt. % of the TADF material E of (c), which is different from the organic molecules of (a). B one or more (additional) fluorescent emitters F different from (e) 0 to 98.8% by weight, preferably 0 to 94% by weight, in particular 0 to 88% by weight, of one or more solvents, wherein at least one, preferably each (additional) fluorescent emitter F (i.e., substance (d)) is present at room temperature (i.e., (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt. %, preferably 2 wt. %, of each S B A small FWHM emitter S in the context of the present invention emits green light with an emission maximum in the recorded emission spectrum between 500 and 560 nm, more preferably between 510 and 550 nm, and even more preferably between 520 and 540 nm from a spin-coated film of B It is.

[0202] In certain embodiments, the total weight of materials in groups (a)-(e) is 100% by weight.

[0203] At least one phosphorescent material P B and at least one organic molecule according to the present invention. Yet another preferred embodiment of the composition comprises at least one organic molecule according to the invention and at least one phosphorescent material P which is not a molecule according to the invention. B(as defined above).

[0204] In this case, at least one organic molecule according to the invention and at least one phosphorescent substance P B Any material selected from the group can act as the emitter material.

[0205] When the emission from the composition is used in an EML of an optoelectronic device, it is predominantly (i.e., 50% or more, preferably 60% or more, more preferably 70% or more, even more preferably more than 80%, or even more preferably more than 90%) emitted by at least one phosphorescent material P. B at least one, preferably each, of the organic molecules according to the invention has a lowest excited singlet state S1 at least one, preferably each, of the phosphorescent material P B Then, one or more, preferably each, of the organic molecules according to the present invention transfers the excitation energy to one or more, preferably each, of the phosphorescent material P B It is preferable to move to

[0206] When the emission from the composition is used in an EML of an optoelectronic device, it is mainly (i.e., 50% or more, preferably 60% or more, more preferably 70% or more, even more preferably 80% or more, or even more preferably 90% or more) attributable to at least one organic molecule according to the present invention, and preferably at least one, preferably each, phosphorescent material P B It is preferred that the lowest excited triplet state T1 of at least one, preferably each, of the phosphorescent material P is higher in energy than the lowest excited triplet state T1 of at least one, preferably each, of the organic molecule according to the present invention. B However, it is preferred that the excitation energy is transferred to at least one, preferably each, organic molecule according to the invention. As mentioned above, the organic molecule according to the invention is a TADF material E as defined herein. BIn this case, it is generally preferred that in the composition at least one, preferably each phosphor P B At least one, preferably each, TADF substance E contained in the composition is activated by the external heavy atom effect. B It is possible to improve the efficiency of RISC processes within a microcontroller and this forms part of the general knowledge of a person skilled in the art.

[0207] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) optionally, one or more host substances H different from the organic molecules of (a); B , (c) one or more phosphorescent substances P different from the organic molecules of (a) B , and (d) optionally one or more solvents; Here, at least one of the materials (a) and / or (c) is an emitter material.

[0208] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention, and (c) one or more phosphorescent substances P different from the organic molecules of (a) B , Here, the fraction (wt%) of the organic molecules of group (a) is the phosphorescent material P of group (c). B and preferably the fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the phosphorescent material P of group (c). B is at least two times higher than the fraction (wt%) of

[0209] In one embodiment, the composition comprises or consists of: (a) 1 to 99.5% by weight, preferably 5 to 50% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.5% by weight, preferably 35 to 94% by weight, in particular 60 to 88% by weight, of one or more host substances H different from the organic molecules of (a). B, (c) 0.5 to 20% by weight, preferably 1 to 15% by weight, in particular 2 to 10% by weight, of one or more phosphorescent substances P different from the organic molecules of (a). B , and (d) 0 to 98.5% by weight, preferably 0 to 59% by weight, in particular 0 to 28% by weight, of one or more solvents, wherein at least one of (a) and / or (c) is an emitter material; In certain embodiments, the total weight of materials from groups (a)-(d) is 100% by weight.

[0210] At least one phosphorescent material P B and a composition comprising at least one organic molecule according to the invention together with at least one (additional) fluorescent emitter F. Yet another preferred embodiment of the composition comprises at least one organic molecule according to the invention and at least one phosphorescent material P which is not a molecule according to the invention. B (as defined above) and at least one (additional) fluorescent emitter F (as defined above) which is not a molecule of the invention.

[0211] In this case, at least one organic molecule according to the invention, at least one phosphorescent substance P B Any substance selected from and the at least one (further) fluorescent emitter F can perform the role of an emitter substance. However, preferably, when used in the EML of an optoelectronic device, the emission from the composition is mainly (i.e. more than 50%, preferably more than 60%, more preferably more than 70%, even more preferably more than 80% or even more preferably more than 90%) attributable to at least one, preferably exactly one (further) fluorescent emitter F which is not a molecule of the invention. At least one, preferably each (further) fluorescent emitter F is dissolved in a solution of 1-5 wt. %, preferably 2 wt. % of each S in poly(methyl methacrylate) (PMMA) at room temperature (i.e. (about) 20° C.). BA small FWHM emitter S in the context of the present invention emits green light with an emission maximum preferably between 500 and 560 nm, more preferably between 510 nm and 550 nm, and even more preferably between 520 and 540 nm in the recorded emission spectrum from a spin-coated film of B It is particularly preferred that the excitation energy is preferably different between the different substances in the composition, in particular between at least one, preferably each, of the host substances H B (if present) to at least one, preferably each, organic molecule according to the present invention and at least one, preferably each, phosphorescent material P B , and at least one, preferably each, (further) fluorescent emitter F. The excitation energy can also be transferred between substances in the composition selected from: at least one organic molecule according to the invention, at least one phosphorescent substance P B and at least one (additional) fluorescent emitter F, in particular at least one, preferably each, organic molecule according to the invention and / or at least one, preferably each, phosphorescent material P B Preferably, the excitation energy is also transferred from at least one, preferably each, organic molecule according to the invention to at least one, preferably each, phosphorescent material P. B can be moved to.

[0212] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (b) optionally, one or more host substances H different from the organic molecules of (a); B , (c) one or more phosphorescent substances P different from the organic molecules of (a) B , (d) The phosphorescent material P in (c) is different from the organic molecule in (a). B one or more fluorescent emitters F different from (e) optionally one or more solvents; wherein at least one, preferably each (additional) fluorescent emitter F (i.e., substance (d)) is present at room temperature (i.e., (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt. %, preferably 2 wt. %, of each S B A small FWHM emitter S in the context of the present invention emits green light with an emission maximum in the recorded emission spectrum between 500 and 560 nm, more preferably between 510 nm and 550 nm, and even more preferably between 520 and 540 nm, from a spin-coated film of B It is.

[0213] In one embodiment, the composition comprises or consists of: (a) one or more organic molecules according to the invention; (c) one or more phosphorescent substances P different from the organic molecules of (a) B , and (d) The phosphorescent material P in (c) is different from the organic molecule in (a). B one or more fluorescent emitters F distinct from Here, the fraction (wt%) of the organic molecules of group (a) is the phosphorescent material P of group (c). B and preferably the fraction (wt%) of the organic molecules of group (a) is higher than the fraction (wt%) of the phosphorescent material P of group (c). B at least twice as high as the fraction (wt%) of Here, the fraction (wt %) of the organic molecules of group (a) is higher than the fraction (wt %) of the fluorescent emitter F of group (d), preferably the fraction (wt %) of the organic molecules of group (a) is at least 5 times higher than the fraction (wt %) of the fluorescent emitter F of group (d).

[0214] In one embodiment, the composition comprises or consists of: (a) 1 to 99.8% by weight, preferably 5 to 50% by weight, in particular 10 to 30% by weight, of one or more organic molecules according to the invention, (b) 0 to 98.8% by weight, preferably 35 to 94% by weight, in particular 60 to 88% by weight, of one or more host substances H different from the organic molecules according to the invention. B , (c) 0.1 to 20% by weight, preferably 0.5 to 10% by weight, in particular 1 to 3% by weight, of one or more phosphorescent substances P different from the organic molecules of (a). B , (d) 0.1 to 20% by weight, preferably 0.5 to 12% by weight, in particular 1 to 5% by weight, of one or more (further) fluorescent emitters F different from the organic molecules of (a), and (e) 0 to 98.8% by weight, preferably 0 to 59% by weight, in particular 0 to 28% by weight, of one or more solvents, wherein at least one, preferably each (further) fluorescent emitter F (i.e., substance (d)) is present at room temperature (i.e., (about) 20° C.) in poly(methyl methacrylate) (PMMA) at a concentration of 1-5 wt. %, preferably 2 wt. %, of each S B A small FWHM emitter S in the context of the present invention emits green light with an emission maximum in the recorded emission spectrum between 500 and 560 nm, more preferably between 510 nm and 550 nm, and even more preferably between 520 and 540 nm, from a spin-coated film of B and In certain embodiments, the total weight of materials in groups (a)-(e) is 100% by weight.

[0215] Further aspects and embodiments of the invention In a preferred embodiment, the organic molecules according to the invention have a photoluminescence quantum yield (PLQY) of 20% or more, more preferably 30% or more, even more preferably 40% or more, particularly 50% or more, particularly 60% or more, especially 70% or more, or even more preferably 80% or more, where the PLQY of the organic molecules according to the invention is determined from a spin-coated film having 10 wt. % of the organic molecules in poly(methyl methacrylate) (PMMA) at room temperature (i.e. (about) 20° C.) as described later in the text.

[0216] In one embodiment of the invention, the organic molecules according to the invention have a delayed excited state lifetime of 50 μs or less, preferably 25 μs or less, more preferably 15 μs or less, even more preferably 10 μs or less, particularly 8 μs or less, in particular 6 μs or less, and especially preferably 4 μs or less, when measured at room temperature (i.e. (about) 20° C.) in a poly(methyl methacrylate) (PMMA) film having 10% by weight of the organic molecules.

[0217] In a further embodiment, the organic molecules according to the present invention have a full width at half maximum (FWHM) of less than 0.60 eV, preferably less than 0.50 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 poly(methyl methacrylate) (PMMA) film having 10% by weight of the organic molecules at room temperature (i.e. (about) 20° C.).

[0218] In a further embodiment, the organic molecules according to the invention have a delayed excited state lifetime of 50 μs or less, preferably 25 μs or less, more preferably 15 μs or less, even more preferably 10 μs or less, particularly 8 μs or less, in particular 6 μs or less, especially preferably 4 μs or less, and a full width at half maximum (FWHM) of less than 0.60 eV, preferably 0.50 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or less than 0.40 eV, in a poly(methyl methacrylate) (PMMA) film having 10 wt. % of the organic molecules at room temperature (i.e. (about) 20° C.).

[0219] In a further embodiment of the present invention, the organic molecules according to the present invention have a full width at half maximum (FWHM) in the visible or near UV range, i.e. in the wavelength range of 380-800 nm, at room temperature (i.e. (about) 20° C.), in a poly(methyl methacrylate) (PMMA) film having 10 wt % of the organic molecules, of less than 0.60 eV, preferably less than 0.50 eV, more preferably less than 0.45 eV, even more preferably less than 0.43 eV, or even more preferably less than 0.40 eV.

[0220] A further aspect of the present invention relates to a method for preparing an organic molecule according to the present invention, comprising a palladium catalyzed cross coupling reaction and a nucleophilic aromatic substitution reaction: [ka]

[0221] According to the invention, at the 2-position, a coupling group CG 1 and at the 4-position is substituted with a coupling group CG 2 Starting from 1-fluorobenzene E2 substituted with , one is coupled with the coupling group CG 3 (reactant E3), and the other is substituted with the coupling group CG 4 (Reactant E4), which is substituted with two heterocycles, is reacted with coupling groups CG 1 and C.G. 4 is C.G. 1 is selected as a reaction pair for introducing the heterocycle of E4 at the position of . Similarly, the coupling group CG 2 and C.G. 3 is C.G. 2 is selected as a reaction pair for introducing the heterocycle of E3 at position 1. Preferably, the so-called Suzuki coupling reaction is used. 1 is selected from Cl, Br or I; CG 4 is a boronic acid or ester group, in particular a pinacol boronic acid ester group, or CG 1 is a boronic acid or ester group, in particular a pinacol boronic acid ester group, and CG 4 is selected from Cl, Br or I. Similarly, CG 2 is selected from Cl, Br or I; CG 3 is a boronic acid or ester group, in particular a pinacol boronic acid ester group, or CG 2 is a boronic acid or ester group, in particular a pinacol boronic acid ester group, and CG3 is selected from Cl, Br or I. Those skilled in the art will appreciate that in order to introduce different heterocycles via the coupling reactions of E3 with E2 and E4 with E2, the intermediate produced by the reaction of the first E2 with E3 can be subsequently reacted with E4 to produce E1, or the intermediate produced by the reaction of the first E2 with E4 can be subsequently reacted with E3 to produce E1.

[0222] For the reaction of nitrogen heterocycles with aryl halides, preferably aryl fluorides, in aromatic nucleophilic substitution reactions, typical conditions include the use of a base such as potassium phosphate or sodium hydride in an aprotic polar solvent such as dimethylsulfoxide (DMSO) or N,N-dimethylformamide (DMF).

[0223] Those skilled in the art are aware of numerous structures that are suitable for reaction of nitrogen heterocycles in aromatic nucleophilic substitution reactions with aryl halides.

[0224] Non-limiting examples of nitrogen heterocycles are listed below (CAS numbers are shown in parentheses below the structures): [ka]

[0225] A further aspect of the present invention relates to a method for producing an optoelectronic component or device, preferably an optoelectronic device, comprising one or more organic molecules according to the present invention.

[0226] A further aspect of the present invention relates to a method for the manufacture of an optoelectronic device, in which an organic molecule according to the present invention or a composition comprising an organic molecule according to the present invention is used.

[0227] Optoelectronic devices, in particular OLEDs, comprising at least one molecule according to the invention may be produced by any means of gas phase deposition and / or liquid processes.

[0228] Known methods for forming the individual layers of an OLED include: - Deposition by sublimation process, -Deposition by organic vapor phase deposition process; - Deposition by carrier gas sublimation process, -Solution processed or printed.

[0229] A further aspect of the invention relates to a method for manufacturing an optoelectronic device, in which an organic molecule according to the invention or a composition comprising an organic molecule according to the invention is used, comprising in particular a step of processing the organic molecule using a vacuum deposition method or from a solution.

[0230] The methods used to manufacture optoelectronic devices, preferably optoelectronic devices such as OLEDs, comprising at least one organic molecule according to the invention are known to those skilled in the art. The different layers are deposited individually and successively on a suitable substrate by subsequent deposition steps. The individual layers can be deposited using the same or different deposition methods.

[0231] The vapor deposition processes include thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active matrix OLED displays, an AMOLED backplane is used as the substrate. The individual layers are also processed from solutions or dispersions using appropriate solvents. For example, solution deposition processes include spin coating, dip coating, and jet printing. Solution processing is optionally performed in an inert atmosphere (e.g., nitrogen atmosphere), and the solvent is completely or partially removed by means known in the art.

[0232] One or more layers are deposited by OVPD (organic vapor phase deposition) process or by -5 Preference is given to optoelectronic elements comprising one or more organic molecules according to the invention, characterized in that they are coated with the aid of carrier gas sublimation applied at pressures between mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the material is applied directly via a nozzle and structured.

[0233] Also preferred are optoelectronic devices comprising one or more organic molecules according to the invention, characterized in that one or more layers are produced from solution, for example by spin-coating, or by any suitable printing process, such as, for example, screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, Thermal Transfer Printing) or inkjet printing. For this, soluble compounds are required. Through suitable substitution of the compounds, high solubility can be achieved.

[0234] For example, a hybrid process is also possible in which one or more layers are applied from solution and one or more additional layers are applied by vapor phase deposition. Thus, for example, an emissive layer can be applied from solution and an electron transport layer can be applied by vapor deposition.

[0235] Those processes / methods are generally known to those skilled in the art and can be applied without inventive steps to organic electroluminescent devices comprising one or more molecules according to the invention.

[0236] In a further aspect, the present invention relates to a method for producing green light, in particular green light of wavelength 500-560 nm, comprising the steps of: (i) providing an optoelectronic device comprising an organic molecule according to the invention; and (ii) applying a current to the element. The core element of an organic electroluminescent device that generates light is at least one light-emitting layer (EML), which is typically located between a positive electrode and a negative electrode. When a voltage (and current) is applied to the positive and negative electrodes of the organic electroluminescent device, holes and electrons are injected from the positive and negative electrodes, respectively. A hole-transporting layer (HTL) is typically located between the light-emitting layer (EML) and the positive electrode, and an electron-transporting layer (ETL) is typically located between the light-emitting layer (EML) and the negative electrode. The different layers are arranged in sequence. Recombination of holes and electrons in the EML then generates high-energy excitons. Decay of such excited states (e.g., singlet states such as S1 and / or triplet states such as T1) to the ground state S0 preferably causes the emission of light.

[0237] Orbital energies, excited state energies and ΔE ST Decision The orbital energies and excited state energies are determined via experimental and quantum chemical methods, in particular computational methods using density functional theory calculations. The highest occupied molecular orbital energy E HOMO is determined from cyclic voltammetry measurements with an accuracy of 0.1 eV by methods known to those skilled in the art.

[0238] TIFF2024513552000109.tif164166

[0239] The absorption spectra are typically recorded at room temperature (i.e., about 20° C.) from spin-coated films of the respective materials in poly(methyl methacrylate) (PMMA). For the organic molecules according to the invention, typically the TADF material E B In the case of phosphorescent material P B In the case of , the concentration of each substance in the spin-coated PMMA film is 10 wt %, unless otherwise stated. The TADF substance E, which is different from the molecules of the present invention and is defined in this application, B Not a host material H B whereas the absorption spectrum is typically BIn the case of non-molecular fluorescent emitters F of the present invention, in particular, they are recorded from a pure film of small FWHM emitters S in the context of the present invention. B In the case of , absorption spectra are recorded from spin-coated films of the respective emitter material, typically with a F concentration of 1-5%, preferably 2% by weight, in PMMA. Alternatively, absorption spectra are also recorded from solutions of the respective molecules, for example in dichloromethane or toluene, where the concentration of the solution is generally chosen such that the maximum absorbance is preferably in the 0.1-0.5 range.

[0240] Unless otherwise stated, the energy of the first excited triplet state T1 is generally determined from the phosphorescence spectrum onset at 77 K (normal state spectrum) from a spin-coated film of the respective material in poly(methyl methacrylate) (PMMA). B For the organic molecules according to the present invention, the phosphorescence spectra are generally recorded at room temperature (i.e., about 20° C.). B In the case of phosphorescent material P B In the case of , the concentration of each substance in the spin-coated PMMA film is 10 wt %, unless otherwise stated. The TADF substance E, which is different from the molecules of the present invention and is defined in this application, B Not a host material H B whereas the absorption spectrum is typically B In the case of non-molecular fluorescent emitters F of the present invention, in particular, they are recorded from a pure film of small FWHM emitters S in the context of the present invention. B where the absorption spectra are recorded from spin-coated films of the respective emitter materials, typically with an F concentration of 1-5%, preferably 2% by weight, in PMMA. ΔE ST TADF material with small value E B In the case of , both intersystem crossing and reverse intersystem crossing can occur even at low temperatures. As a result, the emission spectrum at 77 K contains emission from both the S1 and T1 states. However, the contribution / value of the triplet energy is generally considered to be predominant.

[0241] Unless otherwise stated, the energies of the first excited singlet state S1 are determined from the onset of the fluorescence spectrum (steady state spectrum) at room temperature (i.e. (approximately) 20° C.), typically from spin-coated films of the respective materials in poly(methyl methacrylate) (PMMA). B In the case of , the concentration of each substance in the spin-coated PMMA film is 10 wt %, unless otherwise stated. The TADF substance E, which is different from the molecules of the present invention and is defined in this application, B Not a host material H B whereas the absorption spectrum is typically B In the case of non-molecular fluorescent emitters F of the present invention, in particular, they are recorded from a pure film of small FWHM emitters S in the context of the present invention. B In the case of , absorption spectra are recorded from spin-coated films of the respective emitter materials, typically with F concentrations of 1-5%, preferably 2% by weight, in PMMA. However, phosphorescent materials P that exhibit efficient intersystem crossing B In the case of room temperature emission (typically P in PMMA with 10 wt. % of emitter), B The emission spectrum at room temperature (i.e., (approximately) 20°C) is used to determine the energy of the first excited triplet state T1, but not the energy of the first excited singlet state S1.

[0242] Unless otherwise stated, ΔE corresponds to the energy difference between the first (i.e., lowest) excited singlet state S1 and the first (i.e., lowest) excited triplet state T1. ST The values ​​are determined based on the first excited singlet state energy and the first excited triplet state energy, which are as described above.

[0243] Working Example General synthesis method I Illustratively, general synthetic scheme I provides a synthetic procedure for an organic molecule M1 according to the invention.

[0244] [ka]

[0245] General synthesis method II General synthetic scheme II provides a synthetic approach to organic molecules M2 according to the invention.

[0246] [ka]

[0247] General synthesis method III General synthetic scheme III provides a synthetic approach to organic molecules M2 according to the invention.

[0248] [ka]

[0249] General synthetic procedure: Procedure for Synthetic Scheme I Step 1 Under nitrogen atmosphere, dry dioxane is added to 2,4-dibromo-1-fluorobenzene E1 (1.00 eq., CAS 1435-53-6), bis(pinacolato)diboron E2 (2.40 eq., CAS 73183-34-3), potassium acetate (6.00 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.02 eq., CAS 51364-51-3) and XPhos (0.08, CAS 564483-18-7), followed by nitrogen-sparging for 10 minutes. The reaction mixture is stirred at 100° C. until complete switching of E1 is reached, as judged by GC / MS and TLC. After cooling to room temperature, activated carbon and celite® (kieselgur) are added to the mixture, which is stirred for 15 minutes and then filtered by vacuum suction. The filtrate was extracted with ethyl acetate and brine. The organic extract was concentrated under reduced pressure. The crude product was purified and recrystallized from n-hexane to give P1 as a solid.

[0250] Step 2 Under nitrogen atmosphere, a mixture of dioxane and water (4:1 ratio) is added to boron pinacol ester P1 (1.00 equiv., product of step 1), 2-chloropyrimidine-5-carbonitrile E3 (2.10 equiv., CAS 1753-50-0), tripotassium phosphate (4.00 equiv.), tris(dibenzylideneacetone)dipalladium(0) (0.06 equiv., CAS 51364-51-3), and tricyclohexylphosphine (0.12, CAS 2622-12-2), followed by nitrogen-sparging for 10 min. The reaction mixture is stirred at 100 °C until complete conversion of boron pinacol ester E3 is reached, as judged by GC / MS and TLC. After cooling to room temperature, water is added to the reaction mixture and the resulting precipitate is removed by vacuum suction. The resulting crude product was purified by column chromatography, washing or recrystallization to give P2 as a solid.

[0251] Step 3 P2 (1.00 eq., product of step 2), E4 (1.00 eq.) and potassium carbonate (1.50 eq.) are dissolved in dry DMF under nitrogen atmosphere and stirred at 90° C. for 24 h (the reaction is monitored via LC / MS and TLC). The reaction mixture is then poured into a stirred mixture of water and ice. The resulting precipitate is filtered and washed with water and ethanol. The crude product is purified by column chromatography or recrystallization to give M1 as a solid.

[0252] Procedure for Synthesis Scheme II Step 4 Under nitrogen atmosphere, a mixture of THF and water (4:1 ratio) is added to 3-cyano-4-fluorophenylboronic acid E1' (1.00 equiv., CAS 214210-21-6), halogenated pyrimidine-carbonitrile derivative E3' (1.00 equiv.), potassium carbonate (2.00 equiv.), and [1,1'-]bis(diphenylphosphino)ferrocene)palladium(II) dichloride (0.015 equiv., CAS 72287-26-4) and nitrogen-sparged for 10 min. The reaction mixture is stirred at 80 °C until complete switching of boronic acid E1' is reached, as judged by GC / MS and TLC. After cooling to room temperature, the reaction mixture is extracted with dichloromethane and water. The organic extract is concentrated under reduced pressure. The resulting crude product is purified by column chromatography, washing or recrystallization to give P1' as a solid.

[0253] Step 5 P1' (1.00 eq., product of step 4), E4 (1.00 eq.) and tripotassium phosphate (2.00 eq.) are dissolved in dry DMSO under nitrogen atmosphere and stirred at 80° C. for 24 h (the reaction is monitored via LC / MS and TLC). The reaction mixture is then poured into a stirred mixture of water and ice. The resulting precipitate is filtered and washed with water and ethanol. The crude product is purified by column chromatography, washing or recrystallization to give M2 as a solid.

[0254] Procedure for Synthetic Scheme III Step 6 5-Bromo-2-fluorobenzonitrile E1″ (1.00 equiv.), E4 (1.00 equiv.) and tripotassium phosphate (2.00 equiv.) are dissolved in dry DMSO under nitrogen atmosphere and stirred at 120° C. for 16 h (the reaction is monitored via LC / MS and TLC). The reaction mixture is then poured into a stirred mixture of water and ice. The resulting precipitate is filtered and washed with water and ethanol. The crude product is purified by column chromatography, washing or recrystallization to give P1″ as a solid.

[0255] Step 7 Under nitrogen atmosphere, dry toluene is added to P1″ (1.00 eq., product of step 6), bis(pinacolato)diboron E2 (2.40 eq., CAS 73183-34-3), potassium acetate (6.00 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.02 eq., CAS 51364-51-3) and XPhos (0.08, CAS 564483-18-7), followed by nitrogen-sparging for 10 minutes. The reaction mixture is stirred at 100° C. until complete switching of P1″ is reached, as judged by LCC / MS and TLC. After cooling to room temperature, activated carbon and celite® are added to the mixture, stirred for 15 minutes, and then filtered by vacuum suction. The filtrate is added to n-hexane or methanol to precipitate the crude solid. The resulting crude product was purified by column chromatography or recrystallization to give P2″ as a solid.

[0256] Step 8 Under nitrogen atmosphere, a mixture of dioxane and water (4:1 ratio) was added to P2″ (1.00 equiv., product of step 7), halogenated pyrimidine-carbonitrile derivative E3′ (1.10 equiv.), potassium carbonate (2.00 equiv.), and [1,1′-]bis(diphenylphosphino)ferrocene)palladium(II) dichloride (0.015 equiv., CAS 72287-26-4) and nitrogen-sparged for 10 min. The reaction mixture was stirred at 100 °C until complete conversion of the pinacol boronic ester P2″ was reached as judged by LC / MS and TLC. After cooling to room temperature, water was added to the reaction mixture and the formed precipitate was removed by vacuum suction. The resulting crude product was purified by column chromatography, washing or recrystallization to give M2 as a solid.

[0257] Cyclic Voltammetry Cyclic voltammograms were performed on each compound (e.g., organic molecules according to the present invention, general TADF material E) in dichloromethane, or a suitable solvent, and a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate). B , a common host material H B , common phosphorescent material P B , and a common fluorescent emitter F) with a concentration of 10 -3 The measurement is performed in a solution of 1000 mol / L. The measurement is performed in a nitrogen atmosphere at room temperature (i.e., about 20° C.) using a three-electrode assembly (working electrode and counter electrode: Pt wire, reference electrode: Pt wire). 2 / FeCp 2 + The HOMO and LUMO data were calibrated using ferrocene as an internal standard, with the literature values ​​for ferrocene used for that purpose.

[0258] Density functional theory calculations The molecular structures were optimized using the BP86 function and the Resolution of Identity (RI) approach. The excitation energies were calculated with the Time-Dependent DFT (TD-DFT) method using the (BP86) optimized structures. The orbital energies and excited state energies were calculated with the B3LYP function. For numerical integration, the Def2-SVP basis set and m4-grid were used. The Turbomole program package was used for all calculations.

[0259] optical physical measurements Sample preparation: spin coating Unless otherwise stated, the photophysical measurements of the components were performed on the respective components in poly(methyl methacrylate) (PMMA) (e.g., organic molecules according to the present invention, the general TADF material E B , a common host material H B , common phosphorescent material P B , and common fluorescent emitters F) from spin-coated films. Unless otherwise stated, the component concentrations of such spin-coated PMMA films are as follows: All organic molecules according to the invention: 10% by weight in PMMA A TADF material E as defined herein B : 10% by weight in PMMA A phosphorescent material P as defined herein B : 10% by weight in PMMA Fluorescence emitters F as defined herein, which do not form part of the organic molecules according to the invention, in particular they are small FWHM emitters S in the context of the present invention B In this case: 1 to 5 wt % in PMMA, preferably 2 wt %.

[0260] However, the host material H B is not an organic molecule according to the present invention, but a TADF material E as defined herein. B or phosphorescent material P B or fluorescent emitter F, not H BA spin-coated pure film of is used instead of the PMMA film. Equipment: Spin150, SPS euro Sample concentrations are 1.0 mg / ml and are typically dissolved in a suitable solvent: toluene / DCM. Program: 2000 U / min for 7-30 s. After coating, the film was dried at 70°C for 1 min.

[0261] Absorption measurements A Thermo Scientific Evolution 201 UV-Visible spectrophotometer is used to determine the maximum absorption wavelength of the sample in the wavelength range above 270 nm, which is used as the excitation wavelength for the measurement of the photoluminescence spectrum and quantum yield.

[0262] Photoluminescence spectroscopy For the photoluminescence spectroscopy measurements a Horiba fluorescence spectrometer "Fluoromax 4P" is used.

[0263] Steady-state fluorescence and phosphorescence spectra from phosphorescent emitters are recorded at room temperature. The basic mode of operation is as follows: a continuous light source (a xenon arc lamp) illuminates an excitation monochromator which selects the appropriate wavelength band. This monochromatic excitation light is directed at the sample, which emits light. If the sample is a spin-coated or evaporated film, it is placed in a cuvette and a nitrogen atmosphere is maintained during the measurement. The emitted light is directed to a second emission monochromator which selects a wavelength band that is changed during the measurement and illuminates a photon-counting detector (R928P photomultiplier tube). The signal from the detector is reported to a system controller and host computer which can process and display the data.

[0264] Phosphorescence spectra from the TADF emitter are recorded at 77K. The basic operating scheme is as follows: For excitation, a pulsed light source (pulsed xenon lamp) is used, operating at 25Hz. A control module containing a gate and delay generator is used to control the timing between excitation and sensing. A typical data collection sequence starts with a flash of the pulsed lamp, which is sensed by the control module. Light enters and is dispersed into the excitation monochromator. The monochromator's monochromator's monochromator light excites the sample. The sample is placed in a glass Dewar vessel filled with liquid nitrogen during the measurement. Luminescence emission from the sample is transmitted through the emission monochromator to a photon-counting photomultiplier-tube detector. The control module intercepts the signal from the detector and collects only a gated portion of the flash (initial delay)-only signal for the length of a predefined sampling time (sample window). All signals arriving before or after gating are ignored. The initial delay can be varied from 0 to 10000 ms and is set to eliminate the effects of initial fluorescent emission and lamp decay, preferably 50 ms. The sample window can be varied from 0.01 to 10000 ms and is set to collect phosphorescent emission, preferably 40 ms.

[0265] Time-resolved (transient) photoluminescence (PL) spectroscopy in the μs and ns range (FS5) Time-resolved PL measurements are performed on an Edinburgh Instruments FS5 fluorescence spectrometer. Better light collection compared to measurements on the HORIBA setup allows an optimized signal-to-noise ratio, which makes the FS5 system advantageous, especially in transient PL measurements of delayed fluorescence properties. As a continuous light source the spectrometer contains a 150W xenon arc lamp, the specific wavelength being selected by a Czerny-Turner monochromator. However, standard measurements are instead performed using an external VPLED tunable pulsed LED with an emission wavelength of 310 nm. The sample emission is directed to a sensitive R928P photomultiplier tube (PMT) that is able to detect single photons with a peak quantum efficiency of up to 25% in the spectral range from 200 nm to 870 nm. The detector is a temperature-stabilized PMT that provides dark counts below 300 cps (counts per second). To determine the transient decay time τ of the delayed fluorescence, the data are corrected through the integration of an n-exponential function:

number

number

[0266] Time-Correlated Single Photon Counting (TCSPC) The excited state distribution dynamics are determined using an Edinburgh Instruments FS5 spectrofluorometer equipped with an emission monochromator, a temperature stabilized photomultiplier tube as the detector unit, and a pulsed LED (310 nm central wavelength, 910 ps pulse width) as the excitation source. Samples are placed in cuvettes and flushed with nitrogen during the measurements.

[0267] Overall damping dynamics The entire excited state population decay dynamics over multiple orders of magnitude in time and signal intensity is achieved by performing TCSPC measurements in four time domains (200 ns, 1 μs, 20 μs and longer measurement periods of >80 μs). The measured time curves are then processed in the following manner: 1. The average signal level before excitation and subtracting is determined and background correction is applied. 2. The initial rise of the main signal is taken as the reference and the time axis is aligned. 3. Using the superimposed measured time domains, the curves are scaled relative to each other. 4. The processed curves are merged into one curve.

[0268] Data analysis Data analysis is performed using mono- and bi-exponential fitting of the immediate fluorescence (PF) (typically on the order of nanoseconds) and delayed fluorescence (DF) (typically on the order of microseconds) decays. The ratio of delayed to immediate fluorescence (n value) is calculated by integrating the respective photoluminescence decays over time:

number

[0269] Photoluminescence quantum yield measurement For photoluminescence quantum yield (PLQY) measurements, an Absolute PL quantum yield measurement C9920-03G system (Hamamatsu Photonics) was used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

[0270] Emission maxima are given in nm, quantum yields Φ are given in %, and CIE coordinates are given as x,y values.

[0271] The PLQY is determined using the following protocol: 1) Quality assurance: Anthracene (known concentration) in ethanol is used as the standard. 2) Excitation wavelength: The absorption maximum of the organic molecule is determined and that wavelength is used to excite the molecule. 3) Measurement The quantum yield is measured at room temperature (i.e., about 20° C.) from the spin-coated films as described above in a nitrogen atmosphere. The PLQY is calculated using the following equation:

number

[0272] Fabrication and characterization of optoelectronic devices The optoelectronic device, especially the OLED device, comprising the organic molecules according to the present invention can also be manufactured by vacuum deposition method. When a layer comprises one or more compounds, the weight percentage of one or more compounds is indicated in %. The total weight percentage value is 100%, so when no value is specified, the fraction of the compound is the same as the difference between the specified value and 100%.

[0273] Non-fully optimized OLEDs are characterized by measuring the electroluminescence spectrum using standard methods and the intensity- and current-dependent external quantum efficiency (%) calculated using the light and current detected by a photodiode. The lifetime of the OLED device is extracted from the change in luminance while operating at a constant current density. The LT50 value corresponds to the time when the measured luminance has decreased to 50% of the initial luminance, similarly LT80 corresponds to the point when the measured luminance has decreased to 80% of the initial luminance, and LT95 corresponds to the point when the measured luminance has decreased to 95% of the initial luminance.

[0274] Accelerated lifetime measurements are performed (e.g. by applying increased current densities), e.g. 500cd / m 2 In the present invention, the LT80 value is determined using the following formula:

number

[0275] Values ​​refer to the average of multiple pixels (typically 2-8) and the standard deviation across the pixels is provided. The figures show the data series for one OLED pixel.

[0276] HPLC-MS The purity of organic compounds may be assessed using high pressure liquid chromatography (HPLC) coupled with mass spectrometry (MS). Such HPLC-MS analysis is performed using an Agilent HPLC1260 infinity HPLC-MS system equipped with a single quadrupole MS detector. For example, a typical HPLC method is as follows: a reversed phase column 3.0 mm x 100 mm, 2.7 μm particle size Agilent (Poroshell 120EC-C18, 3.0 x 100 mm, 2.7 μm HPLC column) is used for the HPLC. The HPLC-MS measurements are performed at 45°C with a typical gradient as follows: [Table 1]

[0277] Also, the following solvent mixtures (all solvents contained 0.1% (V / V) formic acid): [Table 2]

[0278] From an analyte solution of 0.5 mg / ml concentration, an injection volume of 2 ml is used for the measurement.

[0279] Ionization of the probe is performed in an APCI (atmospheric pressure chemical ionization) source using positive (APCI+) or negative (APCI-) ionization mode, or using an APPI (atmospheric pressure photoionization) source.

[0280] Example 1 [ka]

[0281] Example 1 was synthesized by Procedure 1 (53% yield), Procedure 2 (62% yield) and Procedure 3 (32% yield), in which 3,6-diphenylcarbazole CAS 56525-79-2 was used as educt E4. MS (HPLC-MS), m / z (retention time): 602.4 (6.61 minutes).

[0282] FIG. 1 shows the emission spectrum of Example 1 (10 wt % in PMMA) at room temperature (i.e., about 20° C.). max The photoluminescence quantum yield (PLQY) is 61%, the full width at half maximum (FWHM) is 0.39 eV, and the emission lifetime is 32.2 μs. The resulting CIEx coordinates are determined to be 0.30 and the CIEy coordinates are determined to be 0.56.

[0283] Example 2 [ka]

[0284] Example 2 was synthesized by Procedure 1 (53% yield), Procedure 2 (62% yield) and Procedure 3 (6% yield), in which 9-phenyl-9H,9″H-[3,3′]bicarbazolyl CAS 1060735-14-9 was used as extract E4. MS (HPLC-MS), m / z (retention time): 691.6 (4.10 minutes).

[0285] FIG. 2 shows the emission spectrum of Example 2 (10 wt % in PMMA) at room temperature (i.e., about 20° C.). max The photoluminescence quantum yield (PLQY) is 41%, the full width at half maximum (FWHM) is 0.43 eV, and the emission lifetime is 17.6 μs. The resulting CIEx coordinates are determined to be 0.36 and the CIEy coordinates are determined to be 0.56.

[0286] Additional Examples of Organic Molecules of the Invention [ka] [ka] JPEG2024513552000124.jpg207141 [ka] [ka] [ka] [ka]

Claims

1. a first chemical moiety comprising the structure of Formula I; and 【Chemistry 1】 ...Chemical formula I An organic molecule comprising a second chemical moiety having the structure of Formula II: 【Chemistry 2】 ...Chemical formula II wherein the first chemical moiety is attached to the second chemical moiety through a single bond; W is a single bond attachment site linking the first chemical moiety to the second chemical moiety; L is a bonding group having the structure of the following chemical formula BN-I, 【Chemistry 3】 ...Chemical formula BN-I wherein the dashed line indicates the binding site depicted in Formula I, # indicates the site of attachment of the first chemical moiety to the second chemical moiety; Z in each occurrence independently represents a direct bond, CR ３ R ４ , C=CR ３ R ４ , C=O, C=NR ３ , N.R. ３ , O, SiR ３ R ４ , S, S(O) and S(O) ２ is selected from the group consisting of R １ and R ２ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, CN, CF ３ , phenyl, C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; C ２ -C ８ Alkenyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; C ２ -C ８ Alkynyl, wherein optionally one or more hydrogen atoms are replaced with deuterium; Optionally, one or more R ６ C substituted with ６ -C １８ Aryl, and Optionally, one or more R ６ C substituted with ３ -C １７ Heteroaryl, R ａ , R ３ and R ４ are, in each occurrence, independently selected from the group consisting of: hydrogen, deuterium, N(R ５ ) ２ 、 OR ５ 、 Si(R ５ ) ３ 、 B(OR ５ ) ２ 、 OSO ２ R ５ 、 CF ３ 、 C.N., F. B, I, C １ -C ４０ Alkyl, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C １ -C ４０ Alkoxy, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C １ -C ４０ Thioalkoxy, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C ２ -C ４０ Alkenyl, This may include one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C ２ -C ４０ Alkynyl, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with Optionally, one or more R ５ C substituted with ６ -C ６０ Aryl, and Optionally, one or more R ５ C substituted with ３ -C ５７ Heteroaryl, R ５ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, N(R ６ ) ２ , OR ６ , Si(R ６ ) ３ , B(OR ６ ) ２ , OSO ２ R ６ 、CF ３ 、CN、F、Br、I、 C １ -C ４０ Alkyl, This may include one or more substituents R ６ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is selectively substituted with C １ -C ４０ Alkoxy, This may be one or more substituents R ６ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is selectively substituted with C １ -C ４０ Thioalkoxy, This may be one or more substituents R ６ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is selectively substituted with C ２ -C ４０ Alkenyl, This may be one or more substituents R ６ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is selectively substituted with C ２ -C ４０ Alkynyl, This may include one or more substituents R ６ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ６ C=CR ６ , C≡C, Si(R ６ ) ２ , Ge(R ６ ) ２ , Sn(R ６ ) ２ , C=O, C=S, C=Se, C=NR ６ , P(=O)(R ６ ), SO, SO ２ , N.R. ６ , O, S or CONR ６ is selectively substituted with Optionally, one or more R ６ C substituted with ６ -C ６０ Aryl, and Optionally, one or more R ６ C substituted with ３ -C ５７ Heteroaryl, R ６ are, in each occurrence, independently selected from the group consisting of: Hydrogen, deuterium, halogens, OPh, CF ３ ,C.N.,F. C １ -C ５ Alkyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, C １ -C ５ Alkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, C １ -C ５ Thioalkoxy, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, C ２ -C ５ Alkenyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, C ２ -C ５ Alkynyl, wherein optionally one or more hydrogen atoms are independently selected from deuterium, CN, CF ３ or is substituted by F, Optionally, one or more C １ -C ５ C substituted with alkyl substituents ６ -C １８ Aryl, Optionally, one or more C １ -C ５ C substituted with alkyl substituents ３ -C １７ Heteroaryl 、 N (C ６ -C １８ Aryl) ２ , N (C ３ -C １７ Heteroaryl) ２ , and N (C ３ -C １７ Heteroaryl) (C ６ -C １８ Aryl), Here, the substituent R ａ , R ３ , R ４ Or R ５ are, independently of one another, one or more substituents R ａ , R ３ , R ４ Or R ５ with the aryloxy group, selectively forming a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system.

2. R １ and R ２ is, in each occurrence, independently of one another, selected from the group consisting of: Hydrogen, deuterium, CN, CF ３ , phenyl, C １ -C ５ Alkyl, Optionally, one or more R ６ C substituted with ６ -C １８ Aryl, and Optionally, one or more R ６ C substituted with ３ -C １７ Heteroaryl.

3. R １ and R ２ 10. The organic molecule of claim 1 , wherein each occurrence is independently selected from the group consisting of hydrogen, methyl and phenyl.

4. 2. The organic molecule of claim 1 , wherein the second chemical moiety comprises the structure of Formula IIa: 【Chemistry 4】 ...Chemical formula IIa.

5. R ａ is, in each occurrence, independently of one another, selected from the group consisting of: hydrogen, deuterium, Me, ｉ Pr、 ｔ This, C.N., CF ３ 、 Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph, optionally substituted with one or more substituents independently selected from the group consisting of Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ pyridinyl optionally substituted with one or more substituents independently selected from the group consisting of: Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph, Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph; Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph, Me, ｉ P.R. ｔ Bu, C.N., C.F. ３ and Ph, optionally substituted with one or more substituents independently selected from the group consisting of N(Ph); ２ , where two adjacent substituents R ａ is substituted with a ring system selected from the group consisting of: 【Chemistry 5】 Here, each dashed line represents R ａ A direct bond is shown connecting one of the ring systems depicted at the position depicted.

6. 2. The organic molecule of claim 1 , wherein the second chemical moiety comprises any one of the following structures: 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】

7. The organic molecule of claim 1, comprising a structure selected from the group consisting of formulas IVa-1, IVb-1, IVc-1, and IVd-1: 【Chemistry 15】 ...Chemical formula IVa-1 【Chemistry 16】 ...Chemical formula IVb-1 【Chemistry 17】 ...Chemical formula IVc-1 【Chemistry 18】 ...Chemical formula IVd-1.

8. The organic molecule of claim 1 comprising a structure selected from the group consisting of formulas VIa-1, VIb-1, VIc-1, and VId-1: 【Chemistry 19】 ...Chemical formula VIa-1 【Chemistry 20】 ...Chemical formula VIb-1 【Chemistry 21】 ...Chemical formula VIc-1 【Chemical 22】 ...Chemical formula VId-1 Where: R ｂ are, in each occurrence, independently selected from the group consisting of: deuterium, N(R ５ ) ２ 、 OR ５ 、 Si(R ５ ) ３ 、 B(OR ５ ) ２ 、 OSO ２ R ５ 、 CF ３ 、 C.N., F. B, I, C １ -C ４０ Alkyl, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C １ -C ４０ Alkoxy, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C １ -C ４０ Thioalkoxy, This may include one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C ２ -C ４０ Alkenyl, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with C ２ -C ４０ Alkynyl, This may be one or more substituents R ５ is selectively substituted with Here, one or more non-adjacent CH ２ The group is R ５ C=CR ５ , C≡C, Si(R ５ ) ２ , Ge(R ５ ) ２ , Sn(R ５ ) ２ , C=O, C=S, C=Se, C=NR ５ , P(=O)(R ５ ), SO, SO ２ , N.R. ５ , O, S or CONR ５ is selectively substituted with Optionally, one or more R ５ C substituted with ６ -C ６０ Aryl, and Optionally, one or more R ５ C substituted with ３ -C ５７ Heteroaryl.

9. An optoelectronic device comprising the organic molecule of claim 1.

10. The optoelectronic device of claim 9, wherein the optoelectronic device is selected from the group consisting of: ・Organic Light Emitting Diode (OLED) Light-emitting electrochemical cells ・OLED sensor ・Organic diode ・Organic solar cells ・Organic transistors ・Organic field effect transistor Organic lasers, and ・Down conversion element.

11. 10. The optoelectronic device according to claim 9, wherein the optoelectronic device is an OLED and comprises the organic molecules in an emissive layer (EML) and / or in a layer directly adjacent to the emissive layer (EML).

12. A composition comprising: an organic molecule according to claim 1, and - a host material H different from the organic molecule Ｂ .

13. Further comprising a fluorescent emitter F different from said organic molecule, 13. The composition according to claim 12, wherein the weight percentage of the organic molecules is higher than the weight percentage of the fluorescent emitter F, and preferably the weight percentage of the organic molecules is at least 5 times higher than the weight percentage of the fluorescent emitter F.

14. 14. A method for the manufacture of an optoelectronic device, in which an organic molecule according to claim 1 or a composition according to claim 12 or claim 13 is used, in particular comprising a step of processing said organic molecule using a vacuum evaporation method or from a solution.

15. (i) providing an optoelectronic device according to claim 9; (ii) applying a current to said element.

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