Organic molecules for optoelectronic devices

Abstract

The invention relates to an organic molecule for use in an optoelectronic device. According to the invention, the organic molecule has a structure of Formula I: wherein X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 and X 14 are independently selected from the group consisting of N and CR a ; and Z is independently at each occurrence selected from the group consisting of a direct bond, CR 3 R 4 , C=CR 3 R 4 , C=O, C=NR 3 , NR 3 , O, SiR 3 R 4 , S, S(O) and S(O)2.

Description

Technical Field

[0001] The invention relates to organic molecules and their use in organic light-emitting diodes (OLEDs) and other optoelectronic devices. Background Technology

[0002] We are actively developing applications of organic molecules in optoelectronic devices. Summary of the Invention

[0003] The purpose of this invention is to provide organic molecules suitable for use in optoelectronic devices.

[0004] This objective is achieved through the invention of a novel organic molecule.

[0005] The invented organic molecules are pure organic molecules, meaning they do not contain any metal ions, unlike known metal complexes used in optoelectronic devices. However, the invented organic molecules may include metalloids (specifically, B, Si, Sn, Se, and / or Ge).

[0006] The invented organic molecule exhibits emission maxima in the blue, sky-blue, green, or yellow spectral ranges. Specifically, the organic molecule exhibits emission maxima between 420 nm and 520 nm (preferably between 440 nm and 495 nm, more preferably between 450 nm and 470 nm), or specifically, between 490 nm and 600 nm (more preferably between 510 nm and 560 nm, even more preferably between 520 nm and 540 nm). Specifically, the photoluminescence quantum yield of the organic molecule according to the invention is 50% or greater. The use of the organic molecule according to the invention in optoelectronic devices (e.g., organic light-emitting diodes (OLEDs)) results in higher efficiency or higher color purity (expressed by the full width at half maximum (FWHM) of the emission). The corresponding OLEDs exhibit higher stability and comparable color compared to OLEDs using known emitter materials.

[0007] The organic molecules according to the invention include or consist of the structure of Formula I:

[0008]

[0009] in,

[0010] X 1 X 2 X 3 X 4 X 5 X 6 X 7 X 8 X9 X 10 X 11 X 12 X 13 and X 14 They are independently selected from N and CR a The group formed;

[0011] Z is selected independently from direct connection key and CR each time it appears. 3 R 4 C = CR 3 R 4 C=O, C=NR 3 NR 3 O, SiR 3 R 4 A group consisting of S, S(O) and S(O)2;

[0012] R 1 and R 2 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 5 )2; OR 5 ;Si(R) 5 )3;B(OR 5 )2; OSO2R 5 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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) 5SO, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 5 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 5 ; and monocyclic or polycyclic aliphatic, aromatic and / or benzofused ring systems, through interaction with R1 R 2 and R 5 One or more of the other substituents in the group form a closed ring;

[0013] R a R 3 and R 4 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 5 )2; OR 5 ;Si(R) 5 )3;B(OR 5 )2; OSO2R 5 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally 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=NR5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C2-C 40 The alkynyl group may optionally be substituted with one or more substituents R. 5 And wherein, one or more non-adjacent CH2 groups are optionally R 5 C = CR 5 C≡C, Si(R) 5 )2、Ge(R 5 )2、Sn(R 5 )2. C=O, C=S, C=Se, C=NR 5 P(=O)(R) 5 SO, SO2, NR 5 O, S or CONR 5 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 5 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 5 ;

[0014] R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; N(R) 6 )2; OR 6 ;Si(R) 6 )3;B(OR 6 )2; OSO2R 6 ;CF3;CN;F;Br;I;C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally R 6 C = CR 6C≡C, Si(R) 6 )2、Ge(R 6 )2、Sn(R 6 )2. C=O, C=S, C=Se, C=NR 6 P(=O)(R) 6 SO, SO2, NR 6 O, S or CONR 6 Replacement; C1-C 40 Alkoxy, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally R 6 C = CR 6 C≡C, Si(R) 6 )2、Ge(R 6 )2、Sn(R 6 )2. C=O, C=S, C=Se, C=NR 6 P(=O)(R) 6 SO, SO2, NR 6 O, S or CONR 6 Replacement; C1-C 40 Thioalkoxy groups, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally R 6 C = CR 6 C≡C, Si(R) 6 )2、Ge(R 6 )2、Sn(R 6 )2. C=O, C=S, C=Se, C=NR 6 P(=O)(R) 6 SO, SO2, NR 6 O, S or CONR 6 Replacement; C2-C 40 Alkenyl, optionally substituted with one or more substituents R 6 And wherein, one or more non-adjacent CH2 groups are optionally R 6 C = CR 6 C≡C, Si(R) 6 )2、Ge(R 6 )2、Sn(R 6 )2. C=O, C=S, C=Se, C=NR 6 P(=O)(R) 6 SO, SO2, NR 6 O, S or CONR 6 Replacement; C2-C 40The alkynyl group may optionally be substituted with one or more substituents R. 6 And wherein, one or more non-adjacent CH2 groups are optionally R 6 C = CR 6 C≡C, Si(R) 6 )2、Ge(R 6 )2、Sn(R 6 )2. C=O, C=S, C=Se, C=NR 6 P(=O)(R) 6 SO, SO2, NR 6 O, S or CONR 6 Replacement; C6-C 60 aryl, optionally substituted with one or more substituents R 6 ; and C3-C 57 Heteroaryl, optionally substituted with one or more substituents R 6 ;

[0015] R 6 Each time it appears, it is independently selected from the group consisting of: hydrogen; deuterium; OPh (Ph = phenyl); CF3; CN; F; C1-C5 alkyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C1-C5 alkoxy, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C1-C5 thioalkoxy, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C2-C5 alkenyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C2-C5 alkynyl, wherein one or more hydrogen atoms are optionally independently substituted by deuterium, CN, CF3 or F; C6-C 18 Aryl group, optionally substituted with one or more C1-C5 alkyl substituents; C3-C 17 Heteroaryl groups, optionally substituted with one or more C1-C5 alkyl substituents; N(C6-C 18 Aryl)2; N(C3-C 17 (heteroaryl)2; and N(C3-C) 17 (C6-C) 18 (Aromatic);

[0016] Among them, substituent R 1 R 2 R a R 3 R 4 or R 5 Independently and optionally with one or more substituents R 1 R2 R a R 3 R 4 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0017] The following shows an example of the selection of organic molecules according to the invention:

[0018]

[0019]

[0020] In one embodiment, the organic molecule according to the invention comprises or is composed of a structure of formula Ia:

[0021]

[0022] in,

[0023] X 1 X 2 X 3 X 12 X 13 and X 14 They are independently selected from N and CR a A group that is formed.

[0024] In one embodiment of the invention, the organic molecule according to the invention comprises or is composed of the structure of formula Ib:

[0025]

[0026] Among them, X 1 X 2 X 3 X 4 X 5 X 6 and X 7 They are independently selected from N and CR a A group that is formed.

[0027] In one embodiment of the invention, the organic molecule according to the invention comprises a structure selected from the group consisting of formulas IIa, IIb, IIc, IId, and IIe, or is composed of a structure selected from the group consisting of formulas IIa, IIb, IIc, IId, and IIe.

[0028]

[0029]

[0030] In a preferred embodiment, the organic molecule according to the invention comprises or is composed of a structure according to formula IIa.

[0031] In a preferred embodiment of the invention, the organic molecule according to the invention comprises a structure selected from the group consisting of formula IIa-1, IIb-1, IIc-1, IId-1 and IIe-1, or is composed of a structure selected from the group consisting of formula IIa-1, IIb-1, IIc-1, IId-1 and IIe-1:

[0032]

[0033]

[0034] In one embodiment of the invention, at least one monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring system is provided by a substituent R. a R 3 R 4 or R 5 With one or more substituents R a R 3 R 4 or R 5 They form together. An example of this structure is shown below:

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042] In a preferred embodiment of the invention, R 1 and R 2 Independently selected from the group consisting of: phenyl, optionally substituted with one or more substituents R 5 ; and pyridyl, optionally substituted with one or more substituents R 5 .

[0043] In another embodiment of the invention, the organic molecule includes a structure selected from the group consisting of formulas IIIa, IIIb, IIIc, IIId, IIIe, IIIf, IIIg, IIIh, and IIIi, or is composed of a structure selected from the group consisting of formulas IIIa, IIIb, IIIc, IIId, IIIe, IIIf, IIIg, IIIh, and IIIi.

[0044]

[0045]

[0046]

[0047] In some embodiments of the invention, Z is a direct-connect key each time it appears.

[0048] In another embodiment of the invention, the organic molecule includes a structure selected from the group consisting of formulas IVa, IVb, IVc, IVd, IVe, IVf, IVg, IVh, and IVi, or is composed of a structure selected from the group consisting of formulas IVa, IVb, IVc, IVd, IVe, IVf, IVg, IVh, and IVi.

[0049]

[0050]

[0051]

[0052] In some embodiments of the invention, selected from X 1 X 2 X 3 X 4 X 5 X 6 X 7 X 8 X 9 X 10 X 11 X 12 X 13 and X 14 The group consisting of fewer than five atoms is N.

[0053] In one embodiment of the invention, selected from X 1 X 2 X 3 X 4 X 5 X 6 X7 X 8 X 9 X 10 X 11 X 12 X 13 and X 14 The group consists of exactly 2n atoms of N, where n is an integer selected from 0, 1, and 2.

[0054]

[0055] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula Ib, wherein both are selected from X. 1 X 2 X 3 X 4 X 5 X 6 and X 7 The two groups in the group each have exactly n atoms of N, where n is an integer selected from 0, 1 and 2.

[0056] In one embodiment, the substituent R 2 and R 1 Same, that is, substituent R 2 Equal to R 1 In other words, R 2 =R 1 .

[0057] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula V:

[0058]

[0059] Among them, substituent R 1 R a R 3 R 4 or R 5 Independently and optionally with one or more substituents R 1 R a R 3 R 4 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0060] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula Va:

[0061]

[0062] Among them, substituent R1 R a or R 5 Independently and optionally with one or more substituents R 1 R a or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0063] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula Vb:

[0064]

[0065] in,

[0066] X 1 X 2 X 3 X 4 X 5 X 6 and X 7 They are independently selected from N and CR a The group formed, and

[0067] Substituent R 1 R a R 3 R 4 or R 5 Independently and optionally with one or more substituents R 1 R a R 3 R 4 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0068] In one embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of formulas Vb-1, Vb-2, Vb-3, Vb-4, Vb-5, Vb-6, Vb-7, Vb-8, and Vb-9, or is composed of a structure selected from the group consisting of formulas Vb-1, Vb-2, Vb-3, Vb-4, Vb-5, Vb-6, Vb-7, Vb-8, and Vb-9.

[0069]

[0070]

[0071]

[0072] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula Vc:

[0073]

[0074] in,

[0075] X 1 X 2 X 3 X 4 X 5 X 6 and X 7 They are independently selected from N and CR a The group formed, and

[0076] Substituent R 1 R a or R 5 Independently and optionally with one or more substituents R 1 R a or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0077] In one embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of formulas Vc-1, Vc-2, Vc-3, Vc-4, Vc-5, Vc-6, Vc-7, Vc-8, and Vc-9, or is composed of a structure selected from the group consisting of formulas Vc-1, Vc-2, Vc-3, Vc-4, Vc-5, Vc-6, Vc-7, Vc-8, and Vc-9.

[0078]

[0079]

[0080]

[0081] In some embodiments of the invention, R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr,t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0082] In some embodiments of the invention, R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; C1-C 40 Alkyl groups, optionally substituted with one or more substituents R 6 ; and C6-C 60 aryl, optionally substituted with one or more substituents R 6 .

[0083] In some embodiments of the invention, R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; C1-C4 alkyl, optionally substituted with one or more substituents R. 6 ; and phenyl, optionally substituted with one or more substituents R 6 .

[0084] In some embodiments of the invention, R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; and Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph.

[0085] In yet another embodiment of the invention, R a Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, tOne or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0086] In yet another embodiment of the invention, R a Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; and a triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph.

[0087] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula VI:

[0088]

[0089] Among them, substituent R 1 R 2 or R 5 Independently and optionally with one or more substituents R 1 R 2 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzo-fused ring systems, and

[0090] Among them, R b Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0091] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula VIa:

[0092]

[0093] Among them, substituent R 1 R 2 or R 5 Independently and optionally with one or more substituents R 1 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0094] In one embodiment of the invention, the organic molecule comprises a structure selected from the group consisting of formulas VIa-1, VIa-2, VIa-3, VIa-4, VIa-5, VIa-6, VIa-7, VIa-8, and VIa-9, or is composed of a structure selected from the group consisting of formulas VIa-1, VIa-2, VIa-3, VIa-4, VIa-5, VIa-6, VIa-7, VIa-8, and VIa-9.

[0095]

[0096]

[0097]

[0098] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula VIb:

[0099]

[0100] Among them, substituent R 1 R 2 or R 5 Independently and optionally with one or more substituents R 1 R 2 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzo-fused ring systems, and

[0101] Among them, R b Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0102] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula VIb-1:

[0103]

[0104] Among them, substituent R 1 or R 5 Independently and optionally with one or more substituents R 1 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0105] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula VIc:

[0106]

[0107] Among them, substituent R 1 R 2 or R 5 Independently and optionally with one or more substituents R 1 R 2 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzo-fused ring systems, and

[0108] Among them, R b Each time it appears, it is independently selected from the group consisting of: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; and N(Ph)2.

[0109] In one embodiment of the invention, the organic molecule comprises or is composed of a structure of formula VIc-1:

[0110]

[0111] Among them, substituent R 1 or R 5 Independently and optionally with one or more substituents R 1 or R 5 Forming monocyclic or polycyclic aliphatic, aromatic, and / or benzofused ring systems.

[0112] In one embodiment of the invention, the organic molecule comprises or is composed of the structure of formula VII:

[0113] Attached Figure Description

[0114] Figure 1 This is the emission spectrum of Example 1 in toluene (0.001 mg / mL). Detailed Implementation

[0115] As used throughout this application, the terms "aryl" and "aromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic aromatic moiety. Thus, an aryl group comprises 6 to 60 aromatic ring atoms, and a heteroaryl group comprises 5 to 60 aromatic ring atoms, at least one of which is a heteroatom. Nevertheless, throughout the application, the number of aromatic ring atoms may be given as a subscript number in the definitions of certain substituents. Specifically, a heteroaromatic ring comprises one to three heteroatoms. Similarly, the terms "heteroaryl" and "heteroaromatic" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic heteroaromatic moiety comprising at least one heteroatom. Heteratoms may be the same or different each time they appear and may be individually selected from the group consisting of N, O, and S. Thus, the term "arylene" refers to a divalent substituent having two binding sites with other molecular structures and thus serving as a linking group structure. Where the group in the exemplary embodiments is defined differently from the definitions given herein (e.g., the number of aromatic ring atoms or the number of heteroatoms differs from the given definitions), the definitions in the exemplary embodiments will apply. According to the invention, the condensed (cyclized) aromatic polycyclic or heteroaromatic polycyclic is composed of two or more monoaromatic or heteroaromatic rings that form a polycyclic structure via a condensation reaction.

[0116] Specifically, as used throughout this document, the term "aryl or heteroaryl" includes groups that can be linked at any position via an aromatic or heteroaromatic group derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, etc. Perylene, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyrene, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenothiazine, pyrazole, indazole, imidazole, benzimidazole, naphthiamidazole, phenanthrenemidazole, pyridinium pyridimazole, pyrazinium pyridimazole, quinoxalineium pyridimazole, oxazole, benzo[a] Oxazole, naphthooxazole, anthraxazole, phenanthreneoxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, 1,3,5-triazine, quinoxaline, pyrazine, phenazine, naphthidine, carboline, benzocarboline, phenanthrene, 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-tetraazine, purine, pteridine, indene, and benzothiadiazole, or combinations of the above groups.

[0117] As used throughout this document, the term "cyclic group" can be understood in the broadest sense as any monocyclic, bicyclic, or polycyclic moiety.

[0118] As used throughout this document, the term "biphenyl" as a substituent can be understood in the broadest sense as ortho-biphenyl, meta-biphenyl, or para-biphenyl, where ortho, meta, and para are defined in relation to the binding site with another chemical moiety.

[0119] As used throughout this document, the term "terphenyl" as a substituent can be understood in the broadest sense as 3-o-terphenyl, 4-o-terphenyl, 4-m-terphenyl, 5-m-terphenyl, 2-m-terphenyl, or 2-para-terphenyl, where ortho, m, and para are defined with respect to the relative positions of the Ph moieties, and "2-", "3-", "4-", and "5-" are defined with respect to the binding site with another chemical moieties, i.e.:

[0120]

[0121] Here, # represents the binding site with another chemical moiety.

[0122] As used throughout this document, the term "naphthyl" as a naphthalene substituent can be understood in the broadest sense as 1-naphthyl and 2-naphthyl, where "1-" and "2-" are defined in relation to the binding site with another chemical moiety, namely:

[0123]

[0124] Here, # represents the binding site with another chemical moiety.

[0125] As used throughout this document, the term "anthrayl" as a substituent can be understood in the broadest sense as 1-anthrayl, 2-anthrayl, and 9-anthrayl, where "1-", "2-", and "9-" are defined in relation to the binding site with another chemical moiety, i.e.:

[0126]

[0127] Here, # represents the binding site with another chemical moiety.

[0128] As used throughout this document, the term "alkyl" can be understood in the broadest sense as any straight-chain, branched, or cyclic alkyl substituent. Specifically, the term alkyl includes substituents such as methyl (Me), ethyl (Et), and n-propyl (...). n Pr), isopropyl ( i Pr), cyclopropyl, n-butyl ( n Bu), isobutyl ( i Bu), sec-butyl (s Bu), tert-butyl ( t Bu), cyclobutyl, 2-methylbutyl, n-pentyl, secondary pentyl, tert-pentyl, 2-pentyl, neopentyl, cyclopentyl, n-hexyl, secondary hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neohexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl, 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1- Bicyclo[2,2,2]octyl, 2-Bicyclo[2,2,2]octyl, 2-(2,6-dimethyl)octyl, 3-(3,7-dimethyl)octyl, adamantyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hexyl-1-yl, 1,1-dimethyl-n-heptyl-1-yl, 1,1-dimethyl-n-octyl-1-yl, 1,1-dimethyl-n-decyl-1-yl, 1,1-dimethyl-n-dodecane-1-yl, 1,1-dimethyl-n-tetradecane-1-yl, 1,1-dimethyl-n-hexadecane-1-yl, 1,1-dimethyl-n-octadecane-1-yl, 1,1-diethyl-n-hexyl-1-yl, 1,1-diethyl-n-heptyl-1-yl, 1,1-diethyl-n-octyl-1-yl, 1,1-diethyl-n-decane-1-yl, 1,1-diethyl-n- Dodecane-1-yl, 1,1-diethyl-n-tetradecane-1-yl, 1,1-diethyl-n-hexadecane-1-yl, 1,1-diethyl-n-octadecane-1-yl, 1-(n-propyl)-cyclohexyl-1-yl, 1-(n-butyl)-cyclohexyl-1-yl, 1-(n-hexyl)-cyclohexyl-1-yl, 1-(n-octyl)-cyclohexyl-1-yl and 1-(n-decyl)-cyclohexyl-1-yl.

[0129] As used throughout, the term "alkenyl" includes straight-chain, branched, and cyclic alkenyl substituents. The term "alkenyl" includes, for example, substituents such as vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, or cyclooctadienyl.

[0130] As used throughout, the term "alkynyl" includes straight-chain, branched, and cyclic alkynyl substituents. Examples of alkynyl substituents include ethynyl, propynyl, butynyl, pentyynyl, hexynyl, heptyynyl, or octyynyl.

[0131] As used throughout, the term "alkoxy" includes straight-chain, branched, and cyclic alkoxy substituents. Exemplary examples of the term "alkoxy" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, and 2-methylbutoxy.

[0132] As used throughout, the term "thioalkoxy" includes straight-chain, branched, and cyclic thioalkoxy substituents in which the O of an alkoxy group is replaced by an S group, as exemplarily described.

[0133] As used throughout, the terms “halogen” and “halogenated” can be understood in the broadest sense as preferably fluorine, chlorine, bromine or iodine.

[0134] Whenever hydrogen (H) is mentioned here, it can also be replaced by deuterium each time it appears.

[0135] It is understood that when a molecular fragment is described as a substituent or otherwise attached to another part, its name may be written as if it were a fragment (e.g., naphthyl, dibenzofuranyl) or as if it were a whole molecule (e.g., naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached fragments are considered equivalent.

[0136] In one embodiment of the invention, the organic molecule according to the invention has an emission peak in the visible or near-ultraviolet range (i.e., in the wavelength range of 380 nm to 800 nm) in an organic solvent having an organic molecule concentration of 0.001 mg / mL at room temperature and a full width at half maximum (FWHM) of less than 0.35 eV (preferably less than 0.30 eV, more preferably less than 0.26 eV, even more preferably less than 0.22 eV or even less than 0.18 eV).

[0137] The energy of the first excited triplet state (T1) is determined by the starting point of the emission spectrum at low temperature (typically 77 K). Phosphorescence is generally visible in the steady-state spectrum in films containing 2 wt% emitter and 98 wt% PMMA. Therefore, the triplet energy can be determined as the starting point of the phosphorescence spectrum. For fluorescent emitter molecules, the energy of the first excited triplet state (T1) is determined by the starting point of the delayed emission spectrum at 77 K.

[0138] The starting point of the emission spectrum is determined by calculating the intersection of the tangent to the emission spectrum with the x-axis. The tangent to the emission spectrum is set at the high-energy side of the emission band and at the point of half maximum intensity of the emission spectrum.

[0139] In one embodiment, the organic molecule according to the invention has an emission spectrum at room temperature in a DCM containing 0.001 mg / mL of organic molecules that is energy close to the starting point of the emission maximum, i.e., the energy difference between the starting point of the emission spectrum and the energy of the emission maximum is less than 0.14 eV (preferably less than 0.13 eV or even less than 0.12 eV), while the full width at half maximum (FWHM) of the organic molecule is less than 0.35 eV (preferably less than 0.30 eV, more preferably less than 0.26 eV, even more preferably less than 0.22 eV or even less than 0.18 eV), such that the CIEy coordinate is less than 0.20 (preferably less than 0.18, more preferably less than 0.16 or even more preferably less than 0.14).

[0140] Another aspect of the invention relates to the application of the organic molecules of the invention in optoelectronic devices as light emitters or absorbers and / or as host materials and / or as electron transport materials and / or as hole injection materials and / or as hole blocking materials.

[0141] Preferred embodiments relate to the application of the organic molecules according to the invention as light emitters in optoelectronic devices.

[0142] Optoelectronic devices can be understood in the broadest sense as any device based on organic materials suitable for emitting visible light or light in the range closest to the ultraviolet (UV) (i.e., wavelengths from 380 nm to 800 nm). More preferably, optoelectronic devices can be capable of emitting light in the visible light range (i.e., wavelengths from 400 nm to 800 nm).

[0143] In this context, optoelectronic devices are more specifically selected from the group consisting of:

[0144] Organic light-emitting diodes (OLEDs);

[0145] • Photoluminescent electrochemical cells;

[0146] • OLED sensors, especially gas and vapor sensors that are not sealed and isolated from the surrounding environment;

[0147] Organic diodes;

[0148] Organic solar cells;

[0149] Organic transistors;

[0150] • Organic field-effect transistors;

[0151] Organic lasers; and

[0152] Down-conversion element.

[0153] In a preferred embodiment within the context of this application, the optoelectronic device is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0154] In this application, the fraction of the organic molecules according to the invention in the emitting layer of the optoelectronic device (more specifically, in an OLED) is from 0.1 wt% to 99 wt% (more specifically, from 1 wt% to 80 wt%). In an alternative embodiment, the proportion of organic molecules in the emitting layer is 100 wt%.

[0155] In one embodiment, the light-emitting layer (or “emitting layer”) comprises not only the organic molecule according to the invention, but also a host material whose triplet (T1) and singlet (S1) energy levels are higher in energy than those of the organic molecule.

[0156] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0157] (a) at least one organic molecule according to the invention, specifically, in the form of an emitter; and

[0158] (b) One or more triplet-triplet annihilation (TTA) host materials that are different from the organic molecule according to the invention; and

[0159] (c) Optionally, one or more TADF materials; and

[0160] (d) Optionally, one or more dyes and / or one or more solvents.

[0161] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0162] (a) at least one organic molecule according to the invention, specifically, in the form of an emitter; and

[0163] (b) One or more host materials that are different from the organic molecule according to the invention; and

[0164] (c) one or more TADF materials; and

[0165] (d) Optionally, one or more dyes and / or one or more solvents.

[0166] Another aspect of the invention relates to a composition comprising or consisting of the following components:

[0167] (a) at least one organic molecule according to the invention, specifically, in the form of an emitter; and

[0168] (b) One or more host materials that are different from the organic molecule according to the invention; and

[0169] (c) one or more phosphorescent materials; and

[0170] (d) Optionally, one or more dyes and / or one or more solvents.

[0171] In a specific embodiment, the light-emitting layer (EML) comprises or is substantially composed of a composition comprising or composed of the following components:

[0172] (i) 0.1% to 10% by weight (preferably 0.5% to 5% by weight, specifically 1% to 3% by weight) of one or more organic molecules (E) according to the invention;

[0173] (ii) at least one host compound (H) comprising 5% to 99% by weight (preferably 15% to 85% by weight, specifically 20% to 75% by weight); and

[0174] (iii) 0.9 wt% to 94.9 wt% (preferably 14.5 wt% to 80 wt%, specifically 24 wt% to 77 wt%) of at least one other main compound (D), the other main compound (D) having a structure different from that of the organic molecule (E) according to the invention; and

[0175] (iv) Optionally, a solvent of 0% to 94% by weight (preferably 0% to 65% by weight, specifically 0% to 50% by weight); and

[0176] (v) Optionally, 0% to 30% by weight (specifically 0% to 20% by weight, preferably 0% to 5% by weight) of at least one other emitter molecule (F), which has a structure different from that of the organic molecule (E) according to the invention.

[0177] Compositions having one or more TTA host materials

[0178] In a preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer (EML) comprises (or is composed of) the following components:

[0179] (i) 10% to 84% by weight of TTA material (H N );

[0180] (ii) 0% to 30% by weight of TADF material (E B );and

[0181] (iii) 0.1% to 10% by weight of the organic molecule (emitter) according to the invention; and optionally

[0182] (iv) 0% to 74% by weight of one or more solvents.

[0183] In a preferred embodiment, the sum of the percentages of (i) to (iv) reaches 100% by weight.

[0184] In another preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer (EML) comprises (or is composed of) the following components:

[0185] (i) 56% to 90% by weight of TTA material (H N );

[0186] (ii) 0% to 5% by weight of TADF material (E B );and

[0187] (iii) 0.5% to 5% by weight of the organic molecule (emitter) according to the invention; and optionally

[0188] (iv) 0% to 34% by weight of one or more solvents.

[0189] In a preferred embodiment, the sum of the percentages of (i) to (iv) reaches 100% by weight.

[0190] Compositions having one or more TADF materials

[0191] In one embodiment, the light-emitting layer (EML) comprises the following components:

[0192] (i) 10% to 89.9% by weight of one or more p-host compounds (H P );

[0193] (ii) 0% to 79.9% by weight of one or more n host compounds (H N );

[0194] (iii) 10% to 50% by weight of one or more TADF materials (E B );and

[0195] (iv) 0.1% to 10% by weight of one or more organic molecules (emitters) according to the invention; and

[0196] (v) 0% to 79.9% by weight of one or more solvents.

[0197] In one embodiment, the light-emitting layer (EML) comprises the following components:

[0198] (i) 22% to 87.5% by weight of one or more p-host compounds (H P );

[0199] (ii) Optionally, from 0% to 65.5% by weight of one or more n host compounds (H N );

[0200] (iii) 12% to 40% by weight of one or more TADF materials (E B );and

[0201] (iv) 0.5% to 5% by weight of one or more organic molecules (emitters) according to the invention; and

[0202] (v) 0% to 65.5% by weight of one or more solvents.

[0203] Composition having one or more phosphorescent materials

[0204] In which H N In an optional preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer (EML) includes (or is composed of) the following components:

[0205] (i) 10% to 84.9% by weight of the main compound (H P );

[0206] (ii) 0% to 84.9% by weight of the main compound (H N );

[0207] (iii) 5% to 15% by weight of phosphorescent material (E B );and

[0208] (iv) 0.1% to 10% by weight of the organic molecule (emitter) according to the invention; and optionally

[0209] (v) 0% to 84.9% by weight of one or more solvents.

[0210] In which H N In an optional preferred embodiment, in the optoelectronic device of the present invention, the light-emitting layer (EML) includes (or is composed of) the following components:

[0211] (i) 22% to 70.5% by weight of the main compound (H P );

[0212] (ii) 0% to 72.5% by weight of the main compound (H N);

[0213] (iii) 5% to 10% by weight of phosphorescent material (E B );and

[0214] (iv) 0.5% to 5% by weight of the organic molecule (emitter) according to the invention; and optionally...

[0215] (v) 0% to 72.5% by weight of one or more solvents.

[0216] Preferably, energy can be transferred from the host compound (H) to one or more organic molecules (E) according to the invention. Specifically, energy can be transferred from the first excited triplet state (T1(H)) of the host compound (H) to the first excited triplet state (T1(E)) of one or more organic molecules (E) according to the invention, and / or from the first excited singlet state (S1(H)) of the host compound (H) to the first excited singlet state (S1(E)) of one or more organic molecules (E) according to the invention.

[0217] In one embodiment, the host compound (H) has an energy (E) in the range of -5 eV to -6.5 eV. HOMO The highest occupied molecular orbital (HOMO(H)) of (H) and at least one other host compound (D) possesses the energy (E) HOMO The highest occupied molecular orbital (HOMO(D)) of E(D)) is where E(D) is located. HOMO (H)>E HOMO (D)

[0218] In yet another embodiment, the host compound (H) possesses energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H), and at least one other host compound (D) possessing the energy (E) LUMO The lowest unoccupied molecular orbital (LUMO(D)) of E(D), where E LUMO (H)>E LUMO (D)

[0219] In one embodiment, the host compound (H) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(H)) and the energy (E) of (H) LUMO The lowest unoccupied molecular orbital (LUMO(H)) of (H) and

[0220] At least one other main compound (D) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(D)) and the energy possessed (E) LUMOThe lowest unoccupied molecular orbital (LUMO(D)) of (D)

[0221] According to the invention, the organic molecule (E) possesses energy (E) HOMO The highest occupied molecular orbital (HOMO(E)) and the energy possessed by (E) LUMO The lowest unoccupied molecular orbital (LUMO(E)) of (E),

[0222] in,

[0223] E HOMO (H)>E HOMO (D), and according to the energy level (E) of the highest occupied molecular orbital (HOMO(E)) of the invented organic molecule (E). HOMO The energy levels of the highest occupied molecular orbital (HOMO(H)) of the host compound (E) and the highest occupied molecular orbital (H) of the host compound (H) (E) HOMO The difference between (H)) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV); and

[0224] E LUMO (H)>E LUMO (D), and according to the invention, the energy level (E) of the lowest unoccupied molecular orbital (LUMO(E)) of the organic molecule (E) LUMO (E)) and the energy level of at least one other host compound D's lowest unoccupied molecular orbital (LUMO(D)) (E) LUMO The difference between (D) is between -0.5 eV and 0.5 eV (more preferably between -0.3 eV and 0.3 eV, even more preferably between -0.2 eV and 0.2 eV, or even between -0.1 eV and 0.1 eV).

[0225] In one embodiment of the invention, the host compound (D) and / or the host compound (H) are thermally activated delayed fluorescence (TADF) materials. TADF materials exhibit fluorescence spectroscopy (FSS) of less than 2500 cm⁻¹. -1 ΔE ST The value of ΔE ST The value corresponds to the energy difference between the first excited singlet state (S1) and the first excited triplet state (T1). Preferably, the TADF material exhibits an energy difference of less than 3000 cm⁻¹. -1 More preferably less than 1500cm -1 or even more preferably less than 1000cm -1 Or even less than 500cm -1 ΔE ST value.

[0226] In one embodiment, the host compound (D) is a TADF material, and the host compound (H) exhibits a thickness greater than 2500 cm⁻¹. -1 ΔE ST Value. In a specific embodiment, the host compound (D) is a TADF material, and the host compound (H) is selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0227] In one embodiment, the host compound (H) is a TADF material, and the host compound (D) exhibits a length greater than 2500 cm⁻¹. -1 ΔE ST Value. In a specific embodiment, the host compound (H) is a TADF material, and the host compound (D) is selected from the group consisting of T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine).

[0228] In another aspect, the invention relates to an optoelectronic device comprising organic molecules or compositions of the type described herein, more specifically in the form of devices selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells, OLED sensors (specifically, gas and vapor sensors that are not externally isolated by a sealed structure), organic diodes, organic solar cells, organic transistors, organic field-effect transistors, organic lasers, and down-conversion elements.

[0229] In a preferred embodiment, the optoelectronic device is selected from the group consisting of organic light-emitting diodes (OLEDs), light-emitting electrochemical cells (LECs), and light-emitting transistors.

[0230] In one embodiment of the optoelectronic device of the invention, the organic molecule (E) according to the invention is used as the emitting material in the light-emitting layer (EML).

[0231] In one embodiment of the optoelectronic device of the invention, the light-emitting layer (EML) is composed of the composition according to the invention described herein.

[0232] When the optoelectronic device is an OLED, it can have, for example, the following layer structure:

[0233] 1. Base

[0234] 2. Anode layer, A

[0235] 3. Hole injection layer, HIL

[0236] 4. Hole transport layer, HTL

[0237] 5. Electron blocking layer, EBL

[0238] 6. Emitting layer, EML

[0239] 7. Hole blocking layer, HBL

[0240] 8. Electron Transport Layer (ETL)

[0241] 9. Electron Injection Layer (EIL)

[0242] 10. Cathode layer, C,

[0243] The OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL and EIL. Optionally, different layers may be combined. The OLED may include more than one layer from each of the layer types defined above.

[0244] In addition, in one embodiment, the optoelectronic device may include one or more protective layers that protect the optoelectronic device from damage caused by exposure to harmful substances in the environment, including, for example, moisture, vapor and / or gases.

[0245] In one embodiment of the invention, the optoelectronic device is an OLED having the following inverted layer structure:

[0246] 1. Base

[0247] 2. Cathode layer, C

[0248] 3. Electron Injection Layer (EIL)

[0249] 4. Electron Transport Layer (ETL)

[0250] 5. Hole blocking layer, HBL

[0251] 6. Emitting layer, EML

[0252] 7. Electron blocking layer, EBL

[0253] 8. Hole Transport Layer (HTL)

[0254] 9. Hole injection layer, HIL

[0255] 10. Anode layer, A,

[0256] The OLED includes each layer selected from the group consisting of HIL, HTL, EBL, HBL, ETL and EIL. Optionally, different layers may be combined. The OLED may include more than one layer from each of the layer types defined above.

[0257] In one embodiment of the invention, the optoelectronic device is an OLED that can have a stacked architecture. In this architecture, contrary to a typical arrangement in which OLEDs are placed side by side, the individual units are stacked on top of each other. Mixed light can be generated using OLEDs exhibiting a stacked architecture; specifically, white light can be generated by stacking blue OLEDs, green OLEDs, and red OLEDs. Furthermore, OLEDs exhibiting a stacked architecture may include a charge generation layer (CGL), which is typically located between two OLED sub-units and typically consists of an n-doped layer and a p-doped layer, with the n-doped layer of a CGL typically located close to the anode layer.

[0258] In one embodiment of the invention, the optoelectronic device is an OLED comprising two or more emitting layers between the anode and cathode. Specifically, this so-called tandem OLED comprises three emitting layers, wherein one emitting layer emits red light, one emitting green light, and one emitting blue light, and optionally, layers such as charge-generating layers, blocking layers, or transport layers may be further included between the respective emitting layers. In another embodiment, the emitting layers are stacked adjacent to each other. In yet another embodiment, the tandem OLED includes a charge-generating layer between every two emitting layers. Additionally, adjacent emitting layers or emitting layers separated by charge-generating layers may be merged.

[0259] The substrate can be formed from any material or combination of materials. Most commonly, a glass substrate is used. Alternatively, a thin metal layer (e.g., a copper, gold, silver, or aluminum film) or a plastic film or substrate can be used. This allows for a higher degree of flexibility. The anode layer (A) is primarily composed of a material that allows for a (substantially) transparent film. Since at least one of the two electrodes should be (substantially) transparent to allow light emission from the OLED, either the anode layer (A) or the cathode layer (C) is transparent. Preferably, the anode layer (A) comprises a large amount of transparent conductive oxide (TCO), or is even composed of transparent conductive oxide (TCO). Such an anode layer (A) can, for example, include indium tin oxide, zinc aluminum 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.

[0260] The anode layer (A) can (basically) be made of indium tin oxide (ITO) (e.g., (InO3)). 0.9 (SnO2)0.1 The anode layer (A) can be composed of a hole injection layer (HIL). The roughness of the anode layer (A) caused by the transparent conductive oxide (TCO) can be compensated by using a hole injection layer (HIL). Furthermore, the HIL can promote the injection of quasi-charge carriers (i.e., holes) because the transport of quasi-charge carriers from the TCO to the hole transport layer (HTL) is facilitated. The hole injection layer (HIL) can include poly(3,4-ethylenedioxythiophene) (PEDOT), polystyrene sulfonate (PSS), MoO2, V2O5, CuPC, or CuI (specifically, a mixture of PEDOT and PSS). The hole injection layer (HIL) also prevents metal from diffusing from the anode layer (A) into the hole transport layer (HTL). HIL can include, for example, PEDOT:PSS (poly(3,4-ethylenedioxythiophene):polystyrene sulfonate), PEDOT (poly(3,4-ethylenedioxythiophene)), mMTDATA (4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine), spiro-TAD (2,2',7,7'-tetra(n,n-diphenylamino)-9,9'-spirodifluorene), DNTPD (N1,N1'-(biphenyl-4,4'-diyl)bis(N1-phenyl-N4,N4-di-m-tolylphenyl-1,4-diamine)), NPB ( N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine), NPNPB (N,N'-diphenyl-N,N'-bis[4-(N,N-diphenyl-amino)phenyl]benzidine), MeO-TPD (N,N,N',N'-tetra(4-methoxyphenyl)benzidine), HAT-CN (1,4,5,8,9,12-hexaazatriphenylhexacarboxynitrile) and / or spiro-NPD (N,N'-diphenyl-N,N'-bis(1-naphthyl)-9,9'-spirodifluorene-2,7-diamine).

[0261] Adjacent to the anode layer (A) or hole injection layer (HIL), a hole transport layer (HTL) is typically positioned. Any hole transport compound can be used here. For example, electron-rich heteroaromatic compounds such as triarylamines and / or carbazole can be used as hole transport compounds. The HTL can lower the energy barrier between the anode layer (A) and the light-emitting layer (EML). The hole transport layer (HTL) can also be an electron blocking layer (EBL). Preferably, the hole transport compound has a relatively high energy level of its triplet state (T1). For example, hole transport layers (HTLs) may include tris(4-carbazole-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenylamine)), α-NPD (N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine), TAPC (4,4'-cyclohexyl-bis[N,N-bis(4-methylphenyl)aniline]), 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine), spiro-TAD, DNTPD, NPB, NPNPB, MeO-T Star-shaped heterocycles of PD, HAT-CN, and / or Tris-Pcz (9,9'-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9'H-3,3'-bicarbazole). Additionally, the HTL may include a p-doped layer composed of inorganic or organic dopants in an organic hole transport matrix. Transition metal oxides such as vanadium oxide, molybdenum oxide, or tungsten oxide can be used, for example, as inorganic dopants. Tetrafluorotetracyanoquinone dimethyl ether (F4-TCNQ), copper pentafluorobenzoate (Cu(I)pFBz), or transition metal complexes can be used, for example, as organic dopants.

[0262] EBLs may include, for example, mCP (1,3-bis(carbazole-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-bis(9H-carbazole-9-yl)biphenyl), Tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole) and / or DCB (N,N'-dicarbazole-1,4-dimethylbenzene).

[0263] Adjacent to the hole transport layer (HTL), a light-emitting layer (EML) is typically positioned. The light-emitting layer (EML) comprises at least one organic molecule. Specifically, the EML comprises at least one organic molecule (E) according to the invention. In one embodiment, the light-emitting layer comprises only the organic molecule according to the invention. Typically, the EML additionally comprises one or more host materials (H). For example, the host material (H) is selected from CBP (4,4'-bis(N-carbazolyl)biphenyl), mCP, mCBP, Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene ... [3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(triphenyl-3-yl)-1,3,5-triazine) and / or TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine). The host material (H) should typically be selected to exhibit first triplet (T1) and first singlet (S1) energy levels that are higher in energy than the first triplet (T1) and first singlet (S1) energy levels of the organic molecule.

[0264] In one embodiment of the invention, the EML comprises a so-called hybrid host system having at least one hole-dominant host and one electron-dominant host. In a specific embodiment, the EML comprises exactly one organic molecule according to the invention and a hybrid host system comprising a T2T as an electron-dominant host and a host selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophene-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophene)phenyl]-9H-carbazole as a hole-dominant host. In another embodiment, the EML comprises 50% to 80% by weight (preferably 60% to 75% by weight) of a body, 10% to 45% by weight (preferably 15% to 30% by weight) of T2T, and 5% to 40% by weight (preferably 10% to 30% by weight) of an organic molecule according to the invention, the body being selected from CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.

[0265] Adjacent to the luminescent layer (EML), an electron transport layer (ETL) may be positioned. Any electron transporter can be used here. Exemplarily, electron-depleted compounds such as benzimidazole, pyridine, triazole, oxadiazole (e.g., 1,3,4-oxadiazole), phosphine oxide, and sulfone can be used. The electron transporter can also be a star-shaped heterocycle such as 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). ETLs may include NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphine oxide), BPyTP2 (2,7-bis(2,2'-bipyridin-5-yl)triphenylene), Sif87 (dibenzo[b,d]thiophene-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophene-2-yldiphenylsilane), BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene) and / or BTB (4,4'-bis[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1'-biphenyl). Optionally, the ETL may be doped with materials such as Liq. Electron transport layer (ETL) can also block holes, or a hole blocking layer (HBL) can be introduced.

[0266] HBLs can include, for example, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), BAlq (bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum), NBphen (2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline), Alq3 (tris(8-hydroxyquinoline)aluminum), and TSPO1 (diphenyl-4-triphenylsilyl) Phenylphosphine oxide), T2T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), T3T (2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine), TST (2,4,6-tris(9,9'-spirodifluorene-2-yl)-1,3,5-triazine) and / or TCB / TCP (1,3,5-tris(N-carbazolyl)benzene / 1,3,5-tris(carbazolyl-9-yl)benzene).

[0267] Adjacent to the electron transport layer (ETL), a cathode layer (C) may be positioned. The cathode layer (C) may, for example, comprise a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy, or may be composed of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, Li, Ca, Ba, Mg, In, W, or Pd) or a metal alloy. For practical reasons, the cathode layer may also be composed of a (substantially) opaque metal such as Mg, Ca, or Al. Optionally or additionally, the cathode layer (C) may also comprise graphite and / or carbon nanotubes (CNTs). Optionally, the cathode layer (C) may also be composed of nanoscale silver wires.

[0268] The OLED may optionally include a protective layer (which may be designated as an electron injection layer (EIL)) between the electron transport layer (ETL) and the cathode layer (C). This layer may include lithium fluoride, cesium fluoride, silver, Liq (lithium 8-hydroxyquinoline), Li2O, BaF2, MgO and / or NaF.

[0269] Optionally, the electron transport layer (ETL) and / or hole blocking layer (HBL) may also include one or more host compounds (H).

[0270] To further modify the emission and / or absorption spectra of the emissive layer (EML), the EML may further include one or more other emitter molecules (F). Such emitter molecules (F) can be any emitter molecule known in the art. Preferably, such emitter molecules (F) are molecules having a structure different from that of the organic molecule (E) according to the invention. The emitter molecule (F) may optionally be a TADF emitter. Alternatively, the emitter molecule (F) may optionally be a fluorescent and / or phosphorescent emitter molecule capable of shifting the emission and / or absorption spectra of the EML. Exemplarily, by emitting light that is typically redshifted compared to light emitted by the organic molecule (E), triplet and / or singlet excitons can transfer from the organic molecule (E) according to the invention to the emitter molecule (F) before relaxing to the ground state (S0). Optionally, the emitter molecule (F) may also induce a two-photon effect (i.e., absorption of half the energy of the maximum absorption value of the two photon pairs).

[0271] Optionally, the optoelectronic device (e.g., OLED) can be a substantially white optoelectronic device. For example, such a white optoelectronic device may include at least one (deep) blue emitter molecule and one or more emitter molecules that emit green and / or red light. Then, energy transmittance may optionally exist between the two or more molecules as described above.

[0272] As used herein, unless otherwise defined in the specific context, the colors of the emitted and / or absorbed light are specified as follows:

[0273] Purple: Wavelength range from >380nm to 420nm;

[0274] Deep blue: wavelength range >420nm to 480nm;

[0275] Sky blue: >480nm to 500nm wavelength range;

[0276] Green: Wavelength range >500nm to 560nm;

[0277] Yellow: Wavelength range >560nm to 580nm;

[0278] Orange: Wavelength range from >580nm to 620nm;

[0279] Red: Wavelength range from 620nm to 800nm.

[0280] For emitter molecules, this color refers to the maximum emission value. Thus, for example, a dark blue emitter has a maximum emission value in the range of >420nm to 480nm, a sky blue emitter has a maximum emission value in the range of >480nm to 500nm, a green emitter has a maximum emission value in the range of >500nm to 560nm, and a red emitter has a maximum emission value in the range of >620nm to 800nm.

[0281] The green emitter can preferably have a maximum emission value between 500 nm and 560 nm (more preferably between 510 nm and 550 nm, and even more preferably between 520 nm and 540 nm).

[0282] Another embodiment of the invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to those of CIEx (=0.170) and CIEy (=0.797), which are the primary color green (CIEx=0.170, CIEy=0.797) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and therefore the OLED is suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). In this context, the term “close to” refers to the range of CIEx and CIEy coordinates provided at the end of this paragraph. In commercial applications, top-emitting devices (with a transparent top electrode) are typically used, while the test device used throughout this application represents a bottom-emitting device (with a transparent bottom electrode and substrate). Therefore, another aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates between 0.06 and 0.34 (preferably between 0.07 and 0.29, more preferably between 0.09 and 0.24, or even more preferably between 0.12 and 0.22, or even more preferably between 0.14 and 0.19) and / or CIEy color coordinates between 0.44 and 0.84 (preferably between 0.55 and 0.83, more preferably between 0.65 and 0.82, or even more preferably between 0.70 and 0.81, or even more preferably between 0.75 and 0.8).

[0283] Therefore, another aspect of the present invention relates to an OLED that has a density of 14500 cd / m². 2It exhibits an external quantum efficiency greater than 10% (more preferably greater than 13%, more preferably greater than 15%, even more preferably greater than 17%, or even more preferably greater than 20%) and / or exhibits a maximum emission value between 495nm and 580nm (preferably between 500nm and 560nm, more preferably between 510nm and 550nm, even more preferably between 515nm and 540nm).

[0284] The deep blue emitter may preferably have a maximum emission value below 480 nm, more preferably below 470 nm, even more preferably below 465 nm, or even below 460 nm. It will typically be above 420 nm, preferably above 430 nm, more preferably above 440 nm, or even above 450 nm.

[0285] Therefore, another aspect of the present invention relates to an OLED that has a density of 1000 cd / m². 2 It exhibits an external quantum efficiency greater than 8% (more preferably greater than 10%, more preferably greater than 13%, even more preferably greater than 15%, or even greater than 20%), and / or exhibits a maximum emission value between 420 nm and 500 nm (preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm), and / or at 500 cd / m². 2 The OLED exhibits an LT80 value greater than 100 hours (preferably greater than 200 hours, more preferably greater than 400 hours, even more preferably greater than 750 hours, or even more preferably greater than 1000 hours). Therefore, another aspect of the invention relates to an OLED whose emission exhibits a CIEy color coordinate of less than 0.45 (preferably less than 0.30, more preferably less than 0.20, or even more preferably less than 0.15, or even more preferably less than 0.10).

[0286] Another aspect of the invention relates to an OLED that emits light at different color points. According to the invention, the OLED emits light having a narrow emission band (small half-peak full width (FWHM)). Specifically, the OLED according to the invention emits light with an FWHM of a main emission peak less than 0.30 eV (preferably less than 0.25 eV, more preferably less than 0.20 eV, even more preferably less than 0.19 eV, or even less than 0.17 eV).

[0287] Another aspect of the invention relates to an OLED that emits light having CIEx and CIEy color coordinates close to CIEx (=0.131) and CIEy (=0.046), CIEx (=0.131) and CIEy (=0.046) color coordinates as the primary color blue (CIEx=0.131, CIEy=0.046) as defined by ITU-R Recommendation BT.2020 (Rec.2020), and therefore the OLED is suitable for use in ultra-high definition (UHD) displays (e.g., UHD-TV). Therefore, another aspect of the present invention relates to an OLED whose emission exhibits CIEx color coordinates between 0.02 and 0.30 (preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20, or even more preferably between 0.08 and 0.18, or even more preferably between 0.10 and 0.15) and / or CIEy color coordinates between 0.00 and 0.45 (preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20, or even more preferably between 0.03 and 0.15, or even more preferably between 0.04 and 0.10).

[0288] In another aspect, the invention relates to a method for manufacturing optoelectronic devices. In this case, the organic molecules of the invention are used.

[0289] The optoelectronic device (specifically, OLED) according to the invention can be fabricated by any method of vapor deposition and / or liquid processing. Therefore, at least one layer:

[0290] -Prepared via sublimation process.

[0291] -Prepared using an organic vapor deposition process.

[0292] -Prepared via carrier gas sublimation process.

[0293] - Solution treatment or printing.

[0294] The method for manufacturing optoelectronic devices (specifically, OLEDs) according to the present invention is known in the art. Different layers are deposited individually and continuously on a suitable substrate via subsequent deposition processes. The individual layers can be deposited using the same or different deposition methods.

[0295] Vapor deposition processes include, for example, thermal (co)evaporation, chemical vapor deposition, and physical vapor deposition. For active-matrix OLED displays, an AMOLED backplane serves as the substrate. Individual layers can be processed from solution or dispersion using suitable solvents. Solution deposition processes include, for example, spin coating, dip coating, and jet printing. Liquid processing can optionally be performed in an inert atmosphere (e.g., in a nitrogen atmosphere), and the solvent can be completely or partially removed by methods known in the art.

[0296] Example

[0297] General Synthesis Scheme I

[0298] Among them, X 1 =X 14 X 2 =X 13 X 3 =X 12 X 4 =X 11 X 5 =X 10 X 6 =X 9 And X 7 =X 8 :

[0299]

[0300] General steps for synthesizing AAV1:

[0301]

[0302] In the first step, acetic acid (50 equivalents) was added to a flask containing 4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole (E0; 1 equivalent) and Zn (1.5 equivalents), and the mixture was stirred at 60°C. Then, the 1,2-diketone compound E1 was added to the obtained compound, and the reaction was stirred at an elevated temperature (30°C or higher) to produce the corresponding 5,8-dibromo-6,7-difluoroquinoxaline derivative E2. Variations in the amount of compound and temperature are permissible.

[0303] General steps for synthesizing AAV2:

[0304]

[0305] The second step is an aromatic nucleophilic substitution reaction between E2 (1 equivalent) and a secondary amine E3 (2.3 equivalents) in an organic solvent (e.g., DMSO, DMF, NMP, DMAc, DME, EtOH, MeCN, Tol, MeCN, or DCM) at elevated temperatures (30°C or higher, and overnight) in the presence of a base (4 equivalents; e.g., K2CO3, K3PO4, NaH, NaOtBu, KOtBu, Cs2CO3, KOH, NaOH, LDA, or LDEA) to obtain the disubstituted compound E4. Variations in the amount of compound, base, solvent, time, and temperature are possible.

[0306] General steps for synthesizing AAV3:

[0307]

[0308] In the final step, in Pd II or Pd o Catalysts (0.05 equivalents; e.g., Pd(OAc)2, PdCl2(PPh3)2, Pd(dppf)Cl2, PdCl2(PPh3)2 or Pd(PPh3)4), ligands (0.08 equivalents; e.g., PPh3, PCy3, PCy3-HBF4, XPhos, S-Phos, R-Phos, xanphos or (tBu)3P), quaternary ammonium salts (1 equivalent; e.g., TBACl, TBAB, TBAI, TBAOH, TM) CH is activated at 140 °C in the presence of AB, THACl, TOACl, tetrabutylammonium tetrafluoroborate or benzyltrimethylammonium bromide, a base (5 equivalents; for example, K2CO3, K3PO4, NaH, NaOtBu, KOtBu, Cs2CO3, KOH or NaOH) and a solvent (for example, DMAc, NMP, DMF, DME, MeCN, Tol, 1,4-dioxane, DMSO, EtOH or THF) to obtain the organic molecule P1 according to the invention. Variations in the amount of compound, phase catalyst, solvent, and temperature are possible.

[0309] General Synthesis Scheme II

[0310]

[0311] General steps for synthesizing AAV2-1:

[0312]

[0313] AAV2-1 is synthesized at ambient temperatures up to 120°C in the presence of a base (1.5 equivalents; e.g., K2CO3, K3PO4, NaH, NaOtBu, KOtBu, Cs2CO3, KOH, NaOH, LDA, or LDEA) and a solvent (e.g., DMSO, DMF, NMP, DMAc, DME, EtOH, MeCN, Tol, MeCN, or DCM) via the reaction of E2 (1.05 equivalents) and a secondary amine E3 (1 equivalent).

[0314] General steps for synthesizing AAV2-2:

[0315]

[0316] The synthesis of E4-2 is carried out by the reaction of E4-1 and the secondary amine E3-2. A solvent (e.g., DMSO, DMF, NMP, DMAc, DME, EtOH, MeCN, Tol, MeCN, or DCM) is added to a flask containing E4-1 (1 equivalent), a base (1.5 equivalent), and E3-2 (1.2 equivalent), and the reaction mixture is stirred for 12 hours at an elevated temperature (50°C or higher). Variations in the amount of compound, base, solvent, and temperature are possible.

[0317] General steps for synthesizing AAV2-3:

[0318]

[0319] For 1 equivalent of E4-2, palladium catalyst (0.05 equivalent; e.g., Pd(OAc)2, PdCl2(PPh3)2, Pd(dppf)Cl2, PdCl2(PPh3)2 or Pd(PPh3)4), ligand (0.08 equivalent; e.g., PPh3, PCy3, PCy3-HBF4, XPhos, S-Phos, R-Phos, xanphos or (tBu)3P), quaternary ammonium salt (1 equivalent; e.g., TBACl, TBAB, TBAI, T BAOH, TMAB, THACl, TOACl, tetrabutylammonium tetrafluoroborate or benzyltrimethylammonium bromide, and a base (5 equivalents; for example, K2CO3, K3PO4, NaH, NaOtBu, KOtBu, Cs2CO3, KOH, NaOH, LDA, or LDEA) are added to a solvent (e.g., MAc, NMP, DMF, DME, MeCN, Tol, 1,4-dioxane, DMSO, THF, or EtOH) and carried out at elevated temperatures (60°C to 160°C). Variations in the amount of compound, phase catalyst, solvent, and temperature are possible.

[0320] General Synthesis Scheme III

[0321] Among them, X 1 =X 14 X 2 =X 13 X 3 =X 12 X 4 =X 11 X 5 =X 10 X 6 =X 9 And X 7 =X 8 :

[0322]

[0323] General steps for synthesizing AAV3-1:

[0324]

[0325] The first step is an aromatic nucleophilic substitution reaction between 4,7-dibromo-5,6-difluorobenzo[c][1,2,5]thiadiazole (E0; 1 equivalent) and a secondary amine E3 (2.1 equivalent) in an organic solvent (e.g., DMSO, DMF, NMP, DMAc, DME, EtOH, MeCN, Tol, MeCN, or DCM) at elevated temperatures (30°C or higher, and overnight) in the presence of a base (4 equivalents; e.g., K2CO3, K3PO4, NaH, NaOtBu, KOtBu, Cs2CO3, KOH, NaOH, LDA, or LDEA) to obtain the disubstituted compound E5. Variations in the amount of compound, base, solvent, time, and temperature are possible.

[0326] General steps for synthesizing AAV3-2:

[0327]

[0328] In the second step, in Pd II or Pd oCatalysts (0.15 equivalents; e.g., Pd(OAc)2, PdCl2(PPh3)2, Pd(dppf)Cl2, PdCl2(PPh3)2 or Pd(PPh3)4), ligands (0.4 equivalents; e.g., PPh3, PCy3, PCy3-HBF4, XPhos, S-Phos, R-Phos, xanphos or (tBu)3P), quaternary ammonium salts (1 equivalent; e.g., TBACl, TBAB, TBAI, TBAOH, TMAB, THAC) The CH activation of E5 (1 equivalent) to yield E6 is carried out in the presence of a base (5 equivalents; e.g., K2CO3, K3PO4, NaH, NaOtBu, KOtBu, Cs2CO3, KOH, or NaOH) and a solvent (e.g., DMAc, NMP, DMF, DME, MeCN, Tol, 1,4-dioxane, DMSO, EtOH, or THF) and at an elevated temperature (60°C or higher, and overnight). Variations in the amount of compound, phase catalyst, solvent, and temperature are possible.

[0329] General steps for synthesizing AAV3-3:

[0330]

[0331] In the final step, acetic acid (50 equivalents) is added to a flask containing E6 (1 equivalent) and Zn (10 equivalents), and the mixture is stirred at 60°C. Then, the 1,2-diketone compound E1 is added to the obtained compound, and the reaction is stirred at an elevated temperature (30°C or higher) to produce the corresponding organic molecule P1 according to the invention. Variations in the amount of compound and temperature are possible.

[0332] Cyclic voltammetry

[0333] Cyclic voltammograms were obtained by reacting a sample in dichloromethane or a suitable solvent with a suitable supporting electrolyte (e.g., 0.1 mol / L tetrabutylammonium hexafluorophosphate) at a concentration of 10... -3 Measurements were taken at a solution concentration of mol / L for organic molecules. Measurements were performed at room temperature under a nitrogen atmosphere using a three-electrode assembly (working and counter electrodes: Pt wires, reference electrode: Pt wires), and using FeCp2 / FeCp2... + Calibration was performed using ferrocene as an internal standard. HOMO data were corrected for the saturated calomel electrode (SCE) using ferrocene as an internal standard.

[0334] Density functional theory calculations

[0335] The molecular structure was optimized using the BP86 functional and the resolution of identity approach (RI). Excitation energies were calculated using the BP86-optimized structure via time-dependent DFT (TD-DFT). Orbital and excited-state energies were calculated using the B3LYP functional. The Def2-SVP basis set and an m4 grid were used for numerical integration. The Turbomole package was used for all calculations.

[0336] Optical physical measurement

[0337] Sample pretreatment: spin coating.

[0338] Instruments: Spin150, SPS euro.

[0339] The sample concentration was 0.2 mg / mL, dissolved in toluene / DCM.

[0340] Program: 7 to 30 seconds at 2000 U / min. After coating, dry the film at 70°C for 1 minute.

[0341] Fluorescence spectroscopy and phosphorescence spectroscopy

[0342] To analyze the phosphorescence and photoluminescence spectra, a fluorescence spectrometer "Fluoromax4P" from Horiba was used.

[0343] Time-resolved PL spectra in the μs and ns ranges (FS5)

[0344] Time-resolved photon (PL) measurements were performed on an FS5 fluorescence spectrometer from Edinburgh Instruments. The improved light collection compared to measurements on HORIBA equipment allows for an optimized signal-to-noise ratio, which supports the FS5 system, especially for transient PL measurements of delayed fluorescence characteristics. The FS5 consists of a xenon lamp providing a broad spectrum. The continuous light source is a 150W xenon arc lamp, and a selected wavelength is chosen via a Czerny-Turner monochromator, which is also used to set a specific emission wavelength. The sample emission is directed to a sensitive R928P photomultiplier tube (PMT), allowing detection of single photons with peak quantum efficiencies up to 25% in the spectral range from 200 nm to 870 nm. The detector is a temperature-stable PMT providing dark counts below 300 cps (counts per second). Finally, to determine the transient decay lifetime of the delayed fluorescence, a tail fit using three exponential functions was applied. This was achieved by using the amplitude A corresponding to a specific lifetime. i For a specific lifetime τ i Weighting,

[0345]

[0346] Determining the delayed fluorescence lifetime τ DF .

[0347] Photoluminescence quantum yield measurement

[0348] For photoluminescent quantum yield (PLQY) measurements, an absolute PL quantum yield measurement system (Hamamatsu Photonics) C9920-03G was used. Quantum yield and CIE coordinates were determined using software version U6039-05 3.6.0.

[0349] The maximum emission value is given in nm, the quantum yield Φ is given in % and the CIE coordinates are given as x and y values.

[0350] PLQY is determined using the following protocol:

[0351] 1) Quality Assurance: Anthracene (known concentration) in ethanol is used as a reference.

[0352] 2) Excitation wavelength: Determine the maximum absorption value of organic molecules and use this wavelength to excite the organic molecules.

[0353] 3) Measurement

[0354] For samples in solution or membrane, quantum yield is measured under a nitrogen atmosphere. Yield is calculated using the equation:

[0355]

[0356] Where, n 光子 Indicates photon count, and Int. indicates intensity.

[0357] Fabrication and characterization of optoelectronic devices

[0358] Optoelectronic devices (such as OLED devices) comprising organic molecules according to the invention can be fabricated via vacuum deposition. If the layer contains more than one compound, the weight percentage of one or more compounds is given as %. The total weight percentage value is 100%, so if no value is given, the fraction of the compound is equal to the difference between the given value and 100%.

[0359] The not-fully-optimized OLED was characterized using standard methods and by measuring the electroluminescence spectrum and intensity-dependent external quantum efficiency (in%), which was calculated using light and current detected by a photodiode. OLED device lifetime was extracted from the change in brightness during operation at a constant current density. The LT50 value corresponds to the time point when the measured brightness decreases to 50% of the initial brightness; similarly, the LT80 value corresponds to the time point when the measured brightness decreases to 80% of the initial brightness, and the LT95 value corresponds to the time point when the measured brightness decreases to 95% of the initial brightness, and so on.

[0360] Accelerated lifetime measurements are performed (e.g., by applying increased current density). For example, the following equation is used to determine the lifetime at 500 cd / m 2 The following LT80 value:

[0361]

[0362] Where L0 represents the initial brightness under the applied current density.

[0363] This value corresponds to the average of several (typically 2 to 8) pixels, giving the standard deviation among these pixels.

[0364] HPLC-MS

[0365] HPLC-MS analysis was performed on an Agilent (1260 series) HPLC system equipped with an MS detector (Thermo LTQ XL).

[0366] For example, a typical HPLC method is as follows: A reversed-phase column from Agilent, 3.0 mm × 100 mm, 2.7 μm particle size (Poroshell 120EC-C18, 3.0 mm × 100 mm, 2.7 μm HPLC column), is used in the HPLC-MS measurement following a gradient at room temperature (rt).

[0367] Flow rate

[0368]

[0369] Use the following solvent mixture containing 0.1% formic acid:

[0370] Solvent A: <![CDATA[H2O(10%)]]> MeCN (90%) Solvent B: <![CDATA[H2O(90%)]]> MeCN (10%) Solvent C: THF (50%) MeCN (50%)

[0371] Measurements were performed using a 2 μL injection volume of an analyte solution with a concentration of 0.5 mg / mL.

[0372] Ionize the probe using an atmospheric pressure chemical ionization (APCI) source in positive (APCI+) or negative (APCI-) ionization mode, or using an atmospheric pressure photoionization (APPI) source.

[0373] Example 1

[0374]

[0375] Synthesize Example 1 according to the following steps:

[0376] AAV1 (69% yield), wherein benzo[134-81-6] was used as E1, the reaction temperature was set at 40°C, and the reaction time was 16 hours;

[0377] AAV2 (82% yield), wherein carbazole [201-696-0] was used as E3, DMF was used as solvent, potassium carbonate [584-08-7] was used as base, the reaction temperature was set at 80°C, and the reaction time was 24 hours; and

[0378] AAV3 (80% yield) was prepared in which Pd(OAC)2 [3375-31-3], PPh3 [603-35-0] and tetrabutylammonium bromide [1643-19-2] were used as catalysts, potassium carbonate [584-08-7] was used as a base, N,N-dimethylacetamide was used as a solvent, the reaction temperature was set at 140°C, and the reaction time was 24 hours.

[0379] Figure 1 The emission spectrum of Example 1 (0.001 mg / mL, in toluene) was depicted. The maximum emission value (λ) max At 461 nm, the photoluminescence quantum yield (PLQY) was 68%, and the full width at half maximum (FWHM) was 0.22 eV. The obtained CIE... x The coordinates are 0.13, CIE y The coordinate is 0.15.

[0380] Example 2

[0381]

[0382] Synthesize Example 2 according to the following steps:

[0383] AAV1 (69% yield), wherein benzo[134-81-6] was used as E1, the reaction temperature was set at 40°C, and the reaction time was 16 hours;

[0384] AAV2 (96% yield), wherein 3,6-diphenyl-9H-carbazole [56525-79-2] was used as E3, DMF was used as the solvent, potassium carbonate [584-08-7] was used as the base, the reaction temperature was set at 80°C, and the reaction time was 24 hours; and

[0385] AAV3 (73% yield) was prepared in which Pd(OAC)2 [3375-31-3], PPh3 [603-35-0] and tetrabutylammonium bromide [1643-19-2] were used as catalysts, potassium carbonate [584-08-7] was used as a base, N,N-dimethylacetamide was used as a solvent, the reaction temperature was set at 140°C, and the reaction time was 36 hours.

[0386] The emission spectrum of Example 2 (0.001 mg / mL, in DCM) has an emission maximum (λ) at 477 nm. maxThe photoluminescent quantum yield (PLQY) was 70%, and the full width at half maximum (FWHM) was 0.21 eV. The obtained CIE... x The coordinates are 0.129, CIE y The coordinates are 0.344.

[0387] Example 3

[0388]

[0389] Synthesize Example 3 according to the following steps:

[0390] AAV3-1 (37% yield), wherein 3,6-di-tert-butylcarbazole [37500-95-1] was used as E3, DMF was used as the solvent, potassium carbonate [584-08-7] was used as the base, the reaction temperature was set at 100°C, and the reaction time was 100 hours; and

[0391] AAV3-2 (54% yield), wherein Pd(OAC)2 [3375-31-3], PPh3 [603-35-0] and tetrabutylammonium bromide [1643-19-2] were used as the catalyst system, potassium carbonate [584-08-7] was used as the base, N,N-dimethylacetamide was used as the solvent, the reaction temperature was set at 140°C, and the reaction time was 3 hours; and

[0392] AAV3-3 (22% yield), wherein cyclohexane-1,2-dione [765-87-7] was used as E1, the reaction temperature was set at 40°C, and the reaction time was 11 hours.

[0393] The emission spectrum of Example 3 (0.001 mg / mL, in toluene) has an emission maximum (λ) at 450 nm. max The photoluminescent quantum yield (PLQY) was 57%, and the full width at half maximum (FWHM) was 0.15 eV. The obtained CIE... x The coordinates are 0.139, CIE y The coordinates are 0.104.

[0394] Example 4

[0395]

[0396] Synthesize Example 4 according to the following steps:

[0397] AAV1 (69% yield), wherein benzo[134-81-6] was used as E1, the reaction temperature was set at 40°C, and the reaction time was 16 hours;

[0398] AAV2 (58% yield), wherein 7H-dibenzo[c,g]carbazole [194-59-2] was used as E3, DMF was used as solvent, potassium carbonate [584-08-7] was used as base, the reaction temperature was set at 100°C, and the reaction time was 24 h; and

[0399] AAV3 (21% yield) was prepared in which Pd(OAC)2 [3375-31-3], PPh3 [603-35-0] and tetrabutylammonium bromide [1643-19-2] were used as catalysts, potassium carbonate [584-08-7] was used as a base, N,N-dimethylacetamide was used as a solvent, the reaction temperature was set at 140°C, and the reaction time was 72 hours.

[0400] The emission spectrum of Example 4 (0.001 mg / mL, in toluene) has an emission maximum (λ) at 501 nm. max The full width at half maximum (FWHM) is 0.13 eV. The obtained CIE... x The coordinates are 0.21, CIE y The coordinates are 0.59.

[0401] Other examples of the invented organic molecules

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

Claims

1. An organic molecule, said organic molecule being selected from formula IIIa, IIIb, IIIc, IIId, IIIe, IIIf, IIIg, IIIh, or IIIi: Formula IIIa Formula IIIb Formula IIIc Formula IIId Formula IIIe Formula IIIf Formula IIIg Formula IIIh Formula IIIi, in, X 1 X 2 X 3 X 4 X 5 X 6 X 7 X 8 X 9 X 10 X 11 X 12 X 13 and X 14 CR is independent of each other a ; or X 1 X 2 X 3 X 4 X 5 X 6 X 9 X 10 X 11 X 12 X 13 and X 14 CR is independent of each other a And X 7 and X 8 N is independent of each other; Z is selected independently from direct connection key and CR each time it appears. 3 R 4 C=O, NR 3 O, S or S(O)2; R a R 3 and R 4 Each time it appears, it is independently selected from: hydrogen; deuterium; N(R) 5 )2; C1-C 40 Alkyl; CN; CF3; Ph, optionally substituted with substances independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; or a triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; R 5 Each time it appears, it is independently selected from: hydrogen; deuterium; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; or N(Ph)2.

2. The organic molecule according to claim 1, wherein, Z is the direct key.

3. The organic molecule according to any one of claims 1 and 2, wherein, R a Each time it appears, it is independently selected from: hydrogen; Me; i Pr; t Bu; CN; CF3; Ph, optionally replacing each other independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; pyridyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; a pyrimidinyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; carbazoyl group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents from the group consisting of Bu, CN, CF3, and Ph; triazine group, optionally substituted with substituents independently selected from Me, i Pr, t One or more substituents in the group consisting of Bu, CN, CF3 and Ph; or N(Ph)2.

4. An organic molecule, said organic molecule being selected from the following compounds: 。 5. The application of an organic molecule according to any one of claims 1 to 4 as a light emitter in an optoelectronic device.

6. The application according to claim 5, wherein, The optoelectronic devices are selected from: • Photoluminescent electrochemical cells; • Organic light-emitting diode (OLED) sensor; • Organic diodes; • Organic solar cells; • Organic transistors; • Organic lasers; or • Down-conversion components.

7. The application according to claim 5, wherein, The optoelectronic devices are selected from: • Organic light-emitting diode; or • Organic field-effect transistors.

8. A composition comprising: (a) The organic molecule according to any one of claims 1 to 4, in the form of an emitter; (b) A triplet-tript annihilation host material that is different from the organic molecule; (c) Optionally, a thermally activated delayed fluorescent material; as well as (d) Optionally, dyes and / or solvents.

9. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 4 or a composition according to claim 8, wherein the optoelectronic device is selected from luminescent electrochemical cells, organic light-emitting diode sensors, organic diodes, organic solar cells, organic transistors, organic lasers, or downconversion elements.

10. An optoelectronic device comprising an organic molecule according to any one of claims 1 to 4 or a composition according to claim 8, wherein the optoelectronic device is selected from organic light-emitting diodes or organic field-effect transistors.

11. The optoelectronic device according to claim 9 or 10, wherein the optoelectronic device comprises: Base; anode; and cathode, wherein the anode or the cathode is disposed on the substrate; as well as A light-emitting layer is disposed between the anode and the cathode and includes the organic molecules or the composition.

12. A method for manufacturing an optoelectronic device, wherein, Use the organic molecule according to any one of claims 1 to 4 or the composition according to claim 8.

13. The method of claim 12, wherein the method comprises the step of treating the organic molecules by vacuum evaporation or from solution.

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