Compounds, semiconductor materials, organic electronic devices, display devices and methods for preparing same

Abstract

The present invention relates to a compound. The present invention further relates to a semiconductor material comprising the compound, an organic electronic device comprising the semiconductor material, a display device comprising the organic electronic device, and a method for preparing the organic electronic device.

Description

Detailed Description of the Invention

[0001] [Technical field] The present invention relates to a compound. The present invention further relates to a semiconductor material comprising the compound, an organic electronic device comprising the semiconductor material, a display device comprising the organic electronic device, and a method for preparing the organic electronic device.

[0002] [Background of the invention] Organic semiconductor devices, such as organic light-emitting diodes (OLEDs), are self-emissive devices that offer wide viewing angles, excellent contrast, fast response, high brightness, excellent operating voltage characteristics, and color reproducibility. A typical OLED consists of an anode, a hole-transporting layer (HTL), an emissive layer (EML), an electron-transporting layer (ETL), and a cathode, which are stacked in sequence on a substrate. The HTL, EML, and ETL are thin films made of organic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode migrate to the EML via the HTL, and electrons injected from the cathode migrate to the EML via the ETL. The holes and electrons recombine in the EML to form excitons. Light is emitted when the excitons decay from their excited state to the ground state. Balanced hole and electron injection and flow are desirable, resulting in OLEDs with the above structure having excellent efficiency and long lifetimes.

[0004] The performance of an organic light-emitting diode can be influenced by the properties of the organic semiconductor layer, and in particular the properties of the organic material of the organic semiconductor layer.

[0005] In particular, in order to apply organic semiconductor devices such as organic light-emitting diodes to large flat panel displays, it is necessary to develop organic semiconductor layers that can increase electron mobility and simultaneously increase electrochemical stability.

[0006] Furthermore, there is a need for the development of organic semiconductor layers that can achieve long lifetimes at high current densities and therefore high brightness. In particular, the development of organic semiconductor materials or layers is necessary to reduce operating voltages, which is important for reducing power consumption and extending battery life in mobile display devices, for example.

[0007] It is therefore an object of the present invention to provide compounds and semiconducting materials for preparing organic electronic and display devices which overcome the drawbacks of the prior art and which have improved performance, in particular lifetime and current efficiency.

[0008] [Disclosure] This object is achieved by compounds of formula (I) [ka] where -A, A' and A'' are substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1-C 20 Alkenyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 independently selected from the group consisting of heteroaryl; -L and L'' are substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 heteroaryl; and L' is H, D, C1-C 20 Alkyl, substituted or unsubstituted C1-C 20 Alkenyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 selected from the group consisting of heteroaryl; or -L is a substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 heteroaryl, wherein L' and L'' together form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or -(substituted or unsubstituted) C6-C 56 substituted with one or more substituents independently selected from aryl, provided that the total number of C atoms of all the substituents does not exceed 56; or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted or at least one of the fused 6-membered aromatic ring and the second 6-membered aromatic ring is a (substituted or unsubstituted) C-C 40 a fused 6-membered aromatic ring substituted with one or more substituents independently selected from aryl, with the proviso that the total number of C atoms of all substituents does not exceed 40; -E is H, D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl; -G is H, D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0009] This object is further achieved according to the invention by a semiconductor material comprising a compound of formula (I).

[0010] This object is further achieved by an organic electronic device comprising a semiconducting layer, which comprises a semiconducting material according to the invention.

[0011] This object is further achieved by a display device comprising an organic electronic device according to the present invention.

[0012] This object is further achieved by a process for preparing an organic electronic device according to the invention, which process comprises depositing a compound according to the invention on a solid support.

[0013] Surprisingly, it has been found that the compounds according to the invention, and the respective semiconducting materials comprising said compounds, can be used for the preparation of organic electronic and display devices having improved properties compared to the respective devices of the prior art, in particular devices having improved lifetime and current efficiency.

[0014] [Compound] According to one aspect, the present invention relates to compounds of formula (I): [ka]

[0015] Unless otherwise expressly stated, all compounds, groups, moieties, substituents, etc., shown herein, particularly by structural formula, systematic name, etc., encompass their respective partially and fully deuterated derivatives.

[0016] In accordance with the present disclosure, in the following bonding scheme formula: [ka] The group R can be attached at any suitable attachment position.

[0017] For example, biphenylene spacers [ka] may be 1,1'-biphenyl-4,4'-diyl; 1,1'-biphenyl-3,4'-diyl; 1,1'-biphenyl-2,4'-diyl; 1,1'-biphenyl-3,3'-diyl; 1,1'-biphenyl-2,3'-diyl; 1,1'-biphenyl-2,2'-diyl.

[0018] In certain embodiments, the biphenylene spacer can have one of the following structures: [ka] Here, the biphenylene spacer is bonded to the following formula at *1, [ka] The biphenylene spacer is bonded to the following formula *2, [ka] and E and G are H, D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0019] A, A' and A'' are substituted or unsubstituted C1-C 20Alkyl, substituted or unsubstituted C1-C 20 Alkenyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 heteroaryl.

[0020] One or more of the substituents on A, A' and A'' when each group is substituted may be D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0021] A, A' and A'' are substituted or unsubstituted C1-C 12 Alkyl, substituted or unsubstituted C1-C 12 Alkenyl, substituted or unsubstituted C6-C 48 Aryl and substituted or unsubstituted C2-C 47 A, A' and A'' can be independently selected from the group consisting of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkenyl, substituted or unsubstituted C6-C6 alkyl, substituted or unsubstituted C6 ... alkenyl, substituted or unsubstituted C6-C6 alkenyl, substituted or unsubstituted C6-C6 alkenyl, substituted or unsubstituted C6-C6 alkenyl, 36 Aryl and substituted or unsubstituted C2-C 36 A, A' and A'' can be independently selected from the group consisting of substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkenyl, substituted or unsubstituted C6-C8 alkyl, substituted or unsubstituted C6-C8 ... 18 Aryl and substituted or unsubstituted C2-C 18A, A', and A'' may be independently selected from the group consisting of substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C1-C4 alkenyl, substituted or unsubstituted phenyl, and substituted or unsubstituted C2-C5 heteroaryl.

[0022] A, A' and A'' are substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 A, A', and A'' can be independently selected from the group consisting of substituted or unsubstituted C-C 48 Aryl and substituted or unsubstituted C2-C 47 A, A', and A'' can be independently selected from the group consisting of substituted or unsubstituted C-C 36 Aryl and substituted or unsubstituted C2-C 36 A, A', and A'' can be independently selected from the group consisting of substituted or unsubstituted C-C 18 Aryl and substituted or unsubstituted C2-C 18 A, A', and A'' may be independently selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted C2-C5 heteroaryl.

[0023] A, A' and A'' are substituted or unsubstituted C6-C 60 A, A', and A'' can be independently selected from the group consisting of substituted or unsubstituted C-C 48 A, A', and A'' can be independently selected from the group consisting of substituted or unsubstituted C-C 36 A, A', and A'' can be independently selected from the group consisting of substituted or unsubstituted C-C 18 A, A', and A" can be independently selected from the group consisting of substituted or unsubstituted phenyl. A, A', and A" can each be unsubstituted phenyl.

[0024] In the first option, L and L″ are substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 and L' is independently selected from the group consisting of H, D, C1-C 20 Alkyl, substituted or unsubstituted C1-C 20 Alkenyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 Heteroaryl is selected from the group consisting of:

[0025] One or more of the substituents on L, L', and L'' when each group is substituted may be D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0026] In this first option, L and L″ are substituted or unsubstituted C6-C 48 Aryl and substituted or unsubstituted C2-C 47 heteroaryl, and L' can be independently selected from the group consisting of H, D, C1-C 12 Alkyl, substituted or unsubstituted C1-C 12 Alkenyl, substituted or unsubstituted C6-C 48 Aryl and substituted or unsubstituted C2-C 47 In this first alternative, L and L" may be selected from the group consisting of substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 35and L' can be independently selected from the group consisting of H, D, C1-C6 alkyl, substituted or unsubstituted C1-C6 alkenyl, substituted or unsubstituted C6-C 36 Aryl and substituted or unsubstituted C2-C 35 In this first alternative, L and L" may be selected from the group consisting of substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 17 and L' can be independently selected from the group consisting of H, D, C1-C4 alkyl, substituted or unsubstituted C1-C4 alkenyl, substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 17 In this first alternative, L and L" can be independently selected from the group consisting of substituted or unsubstituted phenyl, and substituted or unsubstituted C2-C5 heteroaryl, and L' can be selected from the group consisting of H, D, C1-C4 alkyl, substituted or unsubstituted C1-C4 alkenyl, substituted or unsubstituted phenyl, and substituted or unsubstituted C2-C5 heteroaryl.

[0027] In this first option, L and L″ are substituted or unsubstituted C6-C 48 Aryl and substituted or unsubstituted C2-C 47 heteroaryl, and L' can be independently selected from the group consisting of H, D, C1-C 12 Alkyl, substituted or unsubstituted C1-C 12 In this first option, L and L" may be selected from the group consisting of substituted or unsubstituted C6-C alkenyl. 36 Aryl and substituted or unsubstituted C2-C 35 In this first alternative, L and L" can be independently selected from the group consisting of substituted or unsubstituted C6-C6 alkyl, and L' can be selected from the group consisting of H, D, C1-C6 alkyl, and substituted or unsubstituted C1-C6 alkenyl. 18 Aryl and substituted or unsubstituted C2-C 17and L' can be selected from the group consisting of H, D, C1-C4 alkyl, and substituted or unsubstituted C1-C4 alkenyl. In this first alternative, L and L" can be independently selected from the group consisting of substituted or unsubstituted phenyl and substituted or unsubstituted C2-C5 heteroaryl, and L' can be selected from the group consisting of H, D, C1-C4 alkyl, and substituted or unsubstituted C1-C4 alkenyl.

[0028] In this first option, L and L″ are substituted or unsubstituted C6-C 48 aryl, and L' can be selected from the group consisting of H and D. In this first alternative, L and L'' can be substituted or unsubstituted C6-C 36 aryl, and L' can be selected from the group consisting of H and D. In this first alternative, L and L'' can be substituted or unsubstituted C6-C 18 aryl, and L' may be selected from the group consisting of H and D. In this first option, L and L'' may be independently selected from the group consisting of substituted or unsubstituted phenyl, and L' may be selected from the group consisting of H and D. In this first option, L and L'' may be independently selected from the group consisting of substituted or unsubstituted C6-C 60 aryl, and L′ can be H. In this first alternative, L and L″ can each be unsubstituted phenyl, and L′ can be H.

[0029] In the second option, L is a substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C2-C 60 heteroaryl, wherein L′ and L″ together form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or -Substituted or unsubstituted C6-C 56aryl, provided that the total number of C atoms of all substituents does not exceed 56, 56 Aryl substituents include D, halogen, and SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e is optionally further substituted with one or more groups selected from the group consisting of: independently selected from the group consisting of C1-C6 alkyl and phenyl; or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted or at least one of the fused 6-membered aromatic ring and the second 6-membered aromatic ring is a C6-C 40 aryl, provided that the total number of C atoms of all substituents does not exceed 40, 40 Aryl substituents include D, halogen, and SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e may be further substituted with one or more groups selected from the group consisting of: independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0030] For example, when L′ and L″ together form an unsubstituted fused 6-membered aromatic ring, the following structure is formed: [ka] Here, the bond to the remaining structure of formula (I) is *2.

[0031] For example, when L′ and L″ together form a fused 6-membered aromatic ring fused to a second 6-membered aromatic ring, and the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, the following structure can be formed: [ka] Here, the bond to the remaining structure of formula (I) is *2.

[0032] One or more of the substituents on L, L', and L'' when each group is substituted may be D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl), including L 1 and L 2 Also included are substituents on the aryl substituent attached to

[0033] In this second option, L is a substituted or unsubstituted C6-C 48 Aryl and substituted or unsubstituted C2-C 47 heteroaryl, and L′ and L″ together may form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or -Substituted or unsubstituted C6-C 44 substituted with one or more substituents independently selected from aryl, provided that the total number of C atoms of all the substituents does not exceed 44; or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the fused 6-membered aromatic ring and the second 6-membered aromatic ring is a substituted or unsubstituted C-C 28 aryl, with the proviso that the total number of C atoms of all the substituents does not exceed 28.

[0034] In this second option, L is a substituted or unsubstituted C6-C 18 Aryl and substituted or unsubstituted C2-C 47 heteroaryl, and L′ and L″ together may form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or -Substituted or unsubstituted C6-C 14 substituted with one or more substituents independently selected from aryl, provided that the total number of C atoms of all the substituents does not exceed 14; or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the fused 6-membered aromatic ring and the second 6-membered aromatic ring is a substituted or unsubstituted C-C 12 aryl, with the proviso that the total number of C atoms of all the substituents does not exceed 12.

[0035] In this second option, L is a substituted or unsubstituted C6-C 60 aryl, and L′ and L″ together may form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or -Substituted or unsubstituted C6-C 56 aryl, with the proviso that the total number of C atoms of all the substituents does not exceed 56.

[0036] In this second option, L may be selected from the group including substituted or unsubstituted phenyl and substituted or unsubstituted C2-C5 heteroaryl, and L' and L'' together form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or - fused to a second 6-membered aromatic ring, wherein said fused 6-membered aromatic ring and said second 6-membered aromatic ring are unsubstituted.

[0037] In this second option, L can be phenyl, and L′ and L″ together form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or - fused to a second 6-membered aromatic ring, wherein said fused 6-membered aromatic ring and said second 6-membered aromatic ring are unsubstituted.

[0038] E is H, D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0039] E can be independently selected from the group consisting of H, D, C1-C6 alkyl, and C1-C6 alkoxy. E can be independently selected from the group consisting of H, D, and C1-C6 alkyl. E can be independently selected from the group consisting of H and D. Each E can be H.

[0040] G is H, D, halogen, SiR a R b R c (where R a , R b and R c are independently selected from the group consisting of C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN, and P(═O)R d R e (where R d and R e are independently selected from the group consisting of C1-C6 alkyl and phenyl).

[0041] G can be independently selected from the group consisting of H, D, C1-C6 alkyl, and C1-C6 alkoxy. G can be independently selected from the group consisting of H, D, and C1-C6 alkyl. G can be independently selected from the group consisting of H and D. Each G can be H.

[0042] According to one embodiment, the present invention relates to a compound of formula (I): [ka] where -A, A' and A'' are substituted or unsubstituted C6-C 60 independently selected from the group consisting of aryl; -L and L'' are substituted or unsubstituted C6-C 48 aryl, and L' is selected from the group consisting of H and D; or -L is a substituted or unsubstituted C6-C 60aryl, wherein L' and L'' together form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are substituted or unsubstituted; -E is independently selected from the group consisting of H, D, C1-C6 alkyl, and C1-C6 alkoxy; -G is independently selected from the group consisting of H, D, C1-C6 alkyl, and C1-C6 alkoxy.

[0043] According to one embodiment, the present invention relates to a compound of formula (I) [ka] where A, A', and A'' are each unsubstituted phenyl; -L and L'' are each unsubstituted phenyl and L' is H; or -L is unsubstituted phenyl, and L' and L'' together form a fused 6-membered aromatic ring; wherein the fused six-membered aromatic ring is - unsubstituted or or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted; -E is each H; -G is H.

[0044] The compound of formula (I) may be selected from the following compounds E1 to E7:

[0045] [ka]

[0046] [Semiconductor Materials] According to one aspect, the present invention relates to a semiconductor material comprising a compound of formula (I) according to the present invention, as defined herein.

[0047] The semiconductor material may be an organic semiconductor material. The semiconductor material may be an electron transporting material.

[0048] The semiconductor material may comprise the compound of formula (I) in an amount of at least 50 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 60 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 70 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 80 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 90 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 95 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 98 wt.-% based on the total weight of the semiconductor material. The semiconductor material may comprise the compound of formula (I) in an amount of at least 99 wt.-% based on the total weight of the semiconductor material. The semiconductor material may consist essentially of a compound of formula (I).The semiconductor material may consist of a compound of formula (I).

[0049] The semiconductor material may be undoped, or it may be doped with an electrical n-type dopant.

[0050] Under n-type dopant is understood a compound which, when embedded in an electron-transporting matrix material, improves the electronic properties, in particular the electron injection and / or the electronic conductivity, of the formed semiconductor material compared to the untreated electron-transporting matrix material under the same physical conditions.

[0051] In the context of the present invention, "embedded in an electron transport matrix" means intimately mixed with the electron transport matrix.

[0052] The n-type dopant may be selected from elemental metals, metal salts, metal complexes, and organic radicals.

[0053] The metal salt can be selected from alkali metal salts and alkaline earth metal salts, and in one embodiment, can be selected from Li, Na, K, R, Cs, Mg, Ca, Sr, and Ba salts. The salt can include an anion selected from a halogen anion, a complex borate anion, and an organic phenolic acid anion. In one embodiment, the anion in the salt can be a cation-chelating anion such as 8-hydroxyquinolinolate and / or 2-phosphoryl-phenolate.

[0054] In one embodiment, the n-type dopant is selected from alkali metal salts and alkali metal complexes; preferably selected from lithium salts and lithium organic complexes; more preferably selected from lithium halides and lithium organic chelates; even more preferably selected from lithium fluoride, lithium quinolinolate, lithium borate, lithium phenolate, lithium pyridinolate, or lithium complexes with Schiff base ligands; and most preferably selected from lithium fluoride, lithium quinolinolate, lithium borate, lithium phenolate, lithium pyridinolate, or lithium complexes with Schiff base ligands. the lithium complex has formula II, III or IV: [ka] where A1 to A6 are identically or independently selected from CH, CR, N, and O; R are identically or independently selected from hydrogen, halogen, alkyl, or aryl or heteroaryl having 1 to 20 carbon atoms, more preferably A1 to A6 are CH; the borate-based organic ligand is tetra(1H-pyrazol-1-yl)borate, -phenolate is 2-(pyridin-2-yl)phenolate, 2-phosphoryl-phenolate such as 2-(diphenylphosphoryl)phenolate, imidazolephenolate, 2-(pyridin-2-yl)phenolate or 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenolate, -pyridinolate is 2-(diphenylphosphoryl)pyridin-3-olate, - Lithium Schiff bases have the structure 100, 101, 102 or 103. [ka] According to one embodiment of the present invention, the semiconductor material of the present invention comprises a lithium organic complex, alternatively 8-hydroxyquinolinolato-lithium (=LiQ).

[0055] [Organic Electronic Devices] According to one aspect, the present invention relates to an organic electronic device, such as an organic semiconductor device, comprising a semiconducting layer comprising a semiconducting material according to the present invention. The semiconducting layer may comprise a semiconducting material according to the present invention.

[0056] The semiconductor layer may be a hole-blocking layer and / or an electron-transporting layer and / or an electron-injecting layer.The semiconductor layer may be a hole-blocking layer.

[0057] The organic electronic device may further include an anode, a cathode, and an emissive layer, the emissive layer being disposed between the anode and the cathode, and the semiconducting layer being disposed between the emissive layer and the cathode.

[0058] The organic electronic device may further include an anode, a cathode, an emissive layer, and an electron transport layer, the emissive layer and the electron transport layer being disposed between the anode and the cathode, and the semiconducting layer being disposed between the emissive layer and the electron transport layer.

[0059] The organic electronic device may further comprise an anode, a cathode, an emissive layer, and an electron transport layer, wherein the emissive layer and the electron transport layer are disposed between the anode and the cathode, and the semiconducting layer is disposed between the emissive layer and the electron transport layer, and the semiconducting layer is in direct contact with the emissive layer and / or the electron transport layer, preferably in direct contact with the emissive layer and / or the electron transport layer.

[0060] The organic electronic device may further comprise an anode, a cathode, an emissive layer, an electron transport layer and an electron injection layer, wherein the emissive layer, the electron transport layer and the electron injection layer are disposed between the anode and the cathode, and the semiconducting layer is disposed between the emissive layer and the electron transport layer, and the semiconducting layer is in direct contact with the emissive layer and / or the electron transport layer, preferably in direct contact with the emissive layer and / or the electron transport layer.

[0061] The organic electronic device may be an organic light emitting diode.

[0062] The organic electronic device according to the invention may in particular comprise further layers in addition to the semiconducting layer comprising or consisting of the semiconducting material according to the invention. Exemplary embodiments of the respective layers are described below:

[0063] (substrate) The substrate can be any substrate commonly used in the manufacture of electronic devices such as organic light-emitting diodes. If light is emitted through the substrate, the substrate must be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is emitted from the top surface, the substrate can be both transparent and non-transparent materials, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0064] (anode electrode) Either the first electrode or the second electrode included in the organic semiconductor device of the present invention may be an anode electrode. The anode electrode may be formed by evaporating or sputtering a material for forming the anode electrode. The material used to form the anode electrode may be a high work function material to facilitate hole injection. The anode material may also be selected from a low work function material (i.e., aluminum). The anode electrode may be a transparent electrode or a reflective electrode. Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO), aluminum zinc oxide (AlZO), and zinc oxide (ZnO) may be used to form the anode electrode. The anode electrode may also be formed using a metal, typically silver (Ag), gold (Au), or a metal alloy.

[0065] (hole injection layer) The hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, and other methods. When forming the HIL using vacuum deposition, the deposition conditions can vary depending on the compound used to form the HIL and the desired structural and thermal properties of the HIL. However, in general, the vacuum deposition conditions can include a deposition temperature of 100°C to 500°C, a pressure of 10-8 to 10-3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm / s.

[0066] When the HIL is formed using spin coating or printing, the coating conditions can vary depending on the compound used to form the HIL and the desired structural and thermal properties of the HIL. For example, the coating conditions can include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C.

[0067] The HIL can be formed from any compound commonly used to form a HIL. Examples of compounds that can be used to form a HIL include phthalocyanine compounds such as copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonic acid) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), and polyaniline / poly(4-styrenesulfonic acid) (PANI / PSS).

[0068] The HIL may comprise or consist of a p-type dopant, which may be selected from, but is not limited to, tetrafluorotetracyanoquinone dimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile, or 2,2',2''-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile). The HIL may be selected from hole-transporting matrix compounds doped with a p-type dopant. Representative examples of known doped hole-transporting materials include copper phthalocyanine (CuPc) with a HOMO level of approximately -5.2 eV, copper phthalocyanine (CuPc) doped with tetrafluorotetracyanoquinone dimethane (F4TCNQ) with a LUMO level of approximately -5.2 eV, zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV), and α-NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ. α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalonnitrile is also included. The p-type dopant concentration can be selected from 1 to 20 wt.%, preferably 3 to 10 wt.%.

[0069] The thickness of the HIL may be in the range of about 1 nm to about 100 nm, for example, in the range of about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL can have excellent hole injection properties without a substantial penalty in drive voltage.

[0070] (Hole transport layer) The hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for the HIL formation. However, the vacuum deposition or solution deposition conditions may vary depending on the compound used to form the HTL.

[0071] The HTL can be formed using any compound commonly used to form an HTL. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which is incorporated by reference. Examples of compounds that can be used to form the HTL include carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine-based compounds such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA transports holes and inhibits excitons from diffusing into the EML.

[0072] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm. The preferred thickness of the HTL is 170 nm to 200 nm.

[0073] If the thickness of the HTL is within this range, the HTL may have excellent hole transport properties without a substantial penalty in drive voltage.

[0074] (electron blocking layer) The function of the electron blocking layer (EBL) is to block electrons from migrating from the emissive layer to the hole transport layer, thereby confining the electrons to the emissive layer, thereby improving efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound. The triarylamine compound may have a LUMO level closer to the vacuum level than the LUMO level of the hole transport layer. The electron blocking layer may have a HOMO level further away from the vacuum level than the HOMO level of the hole transport layer. The thickness of the electron blocking layer is selected between 2 and 20 nm.

[0075] When the electron blocking layer has a high triplet level, it can also be referred to as a triplet control layer.

[0076] The function of the triplet control layer is to reduce triplet quenching when a phosphorescent green or blue light-emitting layer is used. This can increase the light-emitting efficiency of the phosphorescent light-emitting layer. The triplet control layer is selected from triarylamine compounds having a triplet level higher than that of the phosphorescent emitter in the adjacent light-emitting layer. Compounds suitable for triplet control layers, particularly triarylamine compounds, are described in EP 2 722 908 A1.

[0077] (Photoactive layer (PAL)) The photoactive layer converts electrical current into photons or photons into electrical current.

[0078] The PAL can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the PAL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming the HIL, although the deposition and coating conditions may vary depending on the compound used to form the PAL.

[0079] It can be provided that the photoactive layer does not comprise a compound of formula (1).

[0080] The photoactive layer may be a light-emitting layer or a light-absorbing layer.

[0081] (Emitting Layer (EML)) The EML can be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, etc. When the EML is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for the HIL, although the deposition and coating conditions may vary depending on the compound used to form the EML.

[0082] It can be provided that the light-emitting layer does not comprise a compound of formula (1).

[0083] Each light-emitting layer (EML) can be formed by combining a host and an emitter dopant. Examples of hosts include Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), bis(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)2), EML3 (shown below), Compound 1 (shown below), and Compound 2 (shown below).

[0084] [ka]

[0085] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit via the thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their high efficiency. The emitter may be a small molecule or a polymer.

[0086] Examples of red emitter dopants include, but are not limited to, PtOEP, Ir(πq)3, and Btp2lr(acac). These compounds are phosphorescent emitters, but fluorescent red emitter dopants can also be used.

[0087] [ka]

[0088] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3 shown below. Compound 3 is an example of a fluorescent green emitter, and its structure is shown below.

[0089] [ka]

[0090] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd), and Ir(dfppz)3, ter-fluorene, the structure of which is shown below. 4,4'-bis(4-diphenylamiostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), and compound 4 below are examples of fluorescent blue emitter dopants.

[0091] [ka]

[0092] The amount of the emitter dopant may be in the range of about 0.01 to about 50 parts by weight, based on 100 parts by weight of the host. Alternatively, the light-emitting layer may be composed of a light-emitting polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can have excellent light emission without a substantial disadvantage in driving voltage.

[0093] (Hole Blocking Layer (HBL)) To prevent hole diffusion into the ETL, a hole-blocking layer (HBL) may be formed on the EML by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, etc. If the EML contains a phosphorescent dopant, the HBL may also have a triplet exciton blocking function.

[0094] HBL may also be named auxiliary ETL or a-ETL.

[0095] When forming an HBL using vacuum deposition or spin coating, the deposition and coating conditions are similar to those for forming an HIL. However, the deposition and coating conditions may vary depending on the compound used to form the HBL. Any compound commonly used to form an HBL may be used. Examples of compounds for forming an HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0096] The HBL may have a thickness in the range of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole-blocking properties without a substantial penalty in drive voltage.

[0097] The hole blocking layer may be made of a semiconductor material according to the present invention.

[0098] (Electron transport layer (ETL)) A semiconductor device according to the present invention may include an electron transport layer (ETL).

[0099] According to various embodiments, an OLED can include an electron transport layer or an electron transport layer stack including at least a first electron transport layer and at least a second electron transport layer.

[0100] By properly tuning the energy levels of specific layers in the ETL, electron injection and transport can be controlled and holes can be efficiently blocked, resulting in long lifetimes for OLEDs.

[0101] The electron transport layer can be composed of an ETM material that includes one or more electron transport compounds known in the art.

[0102] According to embodiments, the electron transport layer includes an electron transport compound that contains 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, one or more of which may be substituted with C1-C4 alkyl. In this regard, each aromatic ring or each heteroaromatic ring may be a single aromatic ring, such as a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, or a 5-membered heteroaromatic ring such as pyrrolyl. In fused (hetero)aromatic ring systems, each ring is considered a single ring in this regard. For example, naphthalene contains two aromatic rings.

[0103] The electron transport compound can contain at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, and optionally 1 or 2 heteroaromatic rings.

[0104] The aromatic or heteroaromatic ring of the electron transporting compound may be a six-membered ring.

[0105] The heteroaromatic rings of the electron transport compound can be N-containing heteroaromatic rings, optionally all of the heteroaromatic rings are N-containing heteroaromatic rings, and optionally all of the heteroaromatic rings contain N as the only type of heteroatom.

[0106] The electron transporting compound may contain at least one 6-membered heteroaromatic ring containing 1 to 3 N atoms in each heteroaromatic ring, and optionally 1 to 3 6-membered heteroaromatic rings each containing 1 to 3 N atoms in each heteroaromatic ring.

[0107] At least one six-membered heteroaromatic ring in the electron transporting compound may be an azine, a triazine, a diazine, a pyrazine, a pyrimidine, a pyridine, a quinazoline, or a benzoquinazoline, and preferably a triazine.

[0108] When the electron transporting compound contains two or more heteroaromatic rings, the heteroaromatic rings may be separated from one another by at least one aromatic ring that does not contain a heteroatom.

[0109] In one embodiment, the heteroatom of the heteroaromatic ring of the electron transport compound is attached to the molecular structure of the electron transport compound by at least one double bond.

[0110] The electron transport layer may further include one or more additives. The additive may be an n-type dopant. The additive may be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a transition metal, a transition metal compound, or a rare earth metal. In another embodiment, the metal may be one selected from the group including Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. In another embodiment, the n-type dopant may be one selected from the group including Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. In one embodiment, the alkali metal compound may be 8-hydroxyquinolinolato-lithium (LiQ), lithium tetra(1H-pyrazol-1-yl)borate, or lithium 2-(diphenylphosphoryl)phenolate. Compounds suitable for the ETM (which may be used in addition to the compound of the present invention represented by the general formula (1) defined above) are not particularly limited. In one embodiment, the electron transport matrix compound comprises covalently bonded atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably at least 10, delocalized electrons. In one embodiment, the conjugated system of delocalized electrons may be composed of aromatic or heteroaromatic moieties, as disclosed, for example, in EP 1 970 371 A1 or WO 2013 / 079217 A1.

[0111] The electron transport layer may comprise a compound of formula (I) according to the present invention.

[0112] (Electron injection layer (EIL)) An optional EIL, which facilitates electron injection from the cathode, can be formed directly on the ETL, preferably on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinolphosphate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg, etc., which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the material used to form the EIL.

[0113] The thickness of the EIL may be in the range of about 0.1 nm to about 10 nm, for example, in the range of about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have sufficient electron injection properties without a substantial penalty in drive voltage.

[0114] The electron injection layer may comprise a compound of formula (I) according to the present invention.

[0115] (cathode electrode) If present, a cathode electrode is formed on the EIL. The cathode electrode may be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like. Alternatively, the cathode electrode may be formed of a transparent conductive oxide such as ITO or IZO. The cathode may contain 50% or more by volume of a metal selected from Ag and Au.

[0116] The thickness of the cathode electrode may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode may be transparent or translucent even if it is made of a metal or a metal alloy.

[0117] The cathode may be a semi-transparent metal cathode having a thickness of less than 20 nm, preferably less than 15 nm, and more preferably less than 12 nm.

[0118] It should be understood that the cathode electrode is not part of the electron injection layer or the electron transport layer.

[0119] (charge generating layer / hole generating layer) The charge generation layer (CGL) is composed of a double layer.

[0120] The charge generation layer is a pn junction consisting of an n-type charge generation layer (electron generation layer) and a p-type charge generation layer (hole generation layer). The n-side of the pn junction generates electrons and injects them into the adjacent layer toward the anode. Similarly, the p-side of the pn junction generates holes and injects them into the adjacent layer toward the cathode.

[0121] Charge-generating layers are used in tandem devices, such as tandem OLEDs that contain two or more light-emitting layers between two electrodes. In a tandem OLED with two light-emitting layers, an n-type charge-generating layer provides electrons to a first light-emitting layer located near the anode, and a p-type charge-generating layer provides holes to a second light-emitting layer located between the first light-emitting layer and the cathode.

[0122] The hole-generating layer can be composed of an organic matrix material doped with a p-type dopant. A suitable matrix material for the hole-generating layer may be a material conventionally used as a hole-injecting and / or hole-transporting matrix material. Conventional p-type dopants can be used for the hole-generating layer. For example, the p-type dopant can be one selected from the group consisting of tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, radialene derivatives, iodine, FeCl3, FeF3, and SbCl5. The host may also be one selected from the group including N,N'-di(naphthalen-1-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthyl-benzidine (TNB).

[0123] The n-type charge generating layer can be a layer of a neat n-type dopant, such as an electropositive metal, or can be composed of an organic matrix material doped with an n-type dopant. In one embodiment, the n-type dopant can be an alkali metal, an alkali metal compound, an alkaline earth metal, or an alkaline earth metal compound. In another embodiment, the metal can be one selected from the group including Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. More specifically, the n-type dopant can be one selected from the group including Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. Suitable matrix materials for the electron generating layer can be materials conventionally used as matrix materials for electron injection layers or electron transport layers. Examples of matrix materials can be, for example, one selected from the group including triazine compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminum, benzazole derivatives, and silole derivatives.

[0124] In one embodiment, the p-type charge generating layer may comprise a compound of formula X:

[0125] [ka] Here, each of A1 to A6 can be hydrogen, a halogen atom, nitrile (-CN), nitro (-NO2), sulfonyl (-S02R), sulfoxide (-SOR), sulfonamide (-SON2NR), sulfonate (-S03R), trifluoromethyl (-CF3), ester (-COOR), amide (-CONHR or -CONRR'), substituted or unsubstituted straight-chain or branched C1 to C12 alkoxy, substituted or unsubstituted straight-chain or branched C1 to C12 alkyl, substituted or unsubstituted straight-chain or branched C2 to C12 alkenyl, substituted or unsubstituted aromatic or non-aromatic heterocycle, substituted or unsubstituted aryl, substituted or unsubstituted mono- or di-arylamine, substituted or unsubstituted aralkylamine, or the like. Here, each of the above R and R' can be a substituted or unsubstituted C1 to C60 alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted 5- to 7-membered heterocycle.

[0126] An example of such a p-type charge generating layer can include CNHAT. [ka]

[0127] The hole generating layer may be disposed over the n-type charge generating layer.

[0128] With regard to the method for manufacturing an organic electronic device, the alternative embodiments outlined above may apply mutatis mutandis, for example the charge generating layer may be manufactured using an intermediate layer disposed between the n-type and p-type sublayers.

[0129] According to one embodiment, an OLED according to the present invention can include a layer structure of a substrate disposed adjacent to an anode electrode, the anode electrode disposed adjacent to a first hole injection layer, the first hole injection layer disposed adjacent to a first hole transport layer, the first hole transport layer disposed adjacent to a first electron blocking layer, the first electron blocking layer disposed adjacent to a first light-emitting layer, the first light-emitting layer disposed adjacent to a first electron transport layer, and the first electron transport layer disposed adjacent to an n-type charge generating layer. The n-type charge generating layer is disposed adjacent to the hole generating layer (p-type sublayer), an intermediate layer may be provided between the n-type sublayer and the p-type sublayer, the hole generating layer is disposed adjacent to the second hole transport layer, the second hole transport layer is disposed adjacent to the second electron blocking layer, the second electron blocking layer is disposed adjacent to the second light-emitting layer, and an optional electron transport layer and / or optional injection layer is disposed between the second light-emitting layer and the cathode electrode.

[0130] [Display Device] According to a further aspect, the present invention relates to a display device comprising an organic electronic device according to the present invention, wherein the organic electronic device is an organic light-emitting device.

[0131] [Preparation Process of Organic Electronic Devices] According to a further aspect, the present invention relates to a process for preparing an organic electronic device according to the present invention, which process comprises the step of depositing a compound of formula (I) according to the present invention on a solid support.

[0132] The method for depositing may include: -Deposition by vacuum thermal evaporation method; - Deposition by solution processing, preferably selected from spin coating, printing, casting; and / or -Slot die coating.

[0133] [Details and definitions of the invention] As referred to herein, organic compounds generally refer to any chemical compound containing carbon (excluding those commonly referred to as inorganic compounds such as carbonates, cyanides, carbon dioxide, diamond, etc.) The term organic compound as used herein also encompasses compounds such as organometallic compounds, e.g., metallocenes.

[0134] Unless otherwise expressly stated, all compounds, groups, moieties, substituents, etc., indicated herein, particularly by structural formula, systematic name, etc., encompass their respective partially and fully deuterated derivatives.

[0135] As used herein, the term "zerovalent" refers to a metal in oxidation state 0, i.e., a metal from which no electrons have been removed. Zerovalent metals can exist in the form of zerovalent atoms, neat metals, alloys, etc.

[0136] As used herein, the term "trivalent" refers to a nitrogen atom having a single bond and a double bond and containing a lone pair of electrons.

[0137] The term "hydrocarbyl group" as used herein shall be understood to include any organic group containing carbon atoms, particularly alkyl, aryl, heteroaryl, heteroalkyl and other organic groups, particularly those groups which are common substituents in organic electronics.

[0138] As used herein, the term "conjugated system" refers to a system in which π-bonds and σ-bonds alternate, or a molecule in which single and multiple (i.e., double) bonds alternate, or a system having one or more diatomic structural units in which the π-bond between atoms can be replaced by an atom having at least one lone pair of electrons, typically a divalent O or S atom.

[0139] The term "alkyl" as used herein includes not only straight-chain alkyl but also branched and cyclic alkyl. For example, C3-alkyl can be selected from n-propyl and iso-propyl. Similarly, C4-alkyl includes n-butyl, sec-butyl and t-butyl. Similarly, C6-alkyl includes n-hexyl and cyclohexyl.

[0140] The number n in Cn relates to the total number of carbon atoms in the respective alkyl, arylene, heteroarylene or aryl group.

[0141] As used herein, the term "aryl" or "arylene" encompasses fused aromatic groups such as phenyl (C6-aryl), naphthalene, anthracene, phenanthrene, and tetracene. Furthermore, biphenyls and oligo- or polyphenyls, such as terphenyls, phenyl-substituted biphenyls, and phenyl-substituted terphenyls (e.g., tetraphenylbenzene groups), are also encompassed. "Arylene" refers to a group consisting of two bonded moieties, each of which is a "heteroarylene." As used herein, the term "aryl group" or "arylene group" refers to a group containing at least one hydrocarbon aromatic moiety, where all elements of the hydrocarbon aromatic moiety may have p-orbitals that form conjugation, such as phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrinyl, and fluorenyl groups. Furthermore, spiro compounds, such as 9,9'-spirobi[9H-fluorenyl]yl, in which two aromatic moieties are bonded to each other via a spiro atom, are also encompassed. The aryl or arylene group may contain a monocyclic or fused-ring polycyclic (ie, linked by a linkage sharing adjacent pairs of carbon atoms) functional group.

[0142] As used herein, the term "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced with a heteroatom. The term "heteroaryl" may refer to an aromatic heterocycle having at least one heteroatom, and all atoms in the hydrocarbon heteroaromatic moiety may have p-orbitals that form conjugation. A heteroarylene ring may contain at least 1 to 3 heteroatoms. As with "aryl" / "arylene," the term "heteroaryl" includes spiro compounds in which two aromatic moieties are linked together, such as spiro[fluorene-9,9'-xanthene]. Further exemplary heteroaryl groups are diazines, triazines, dibenzofurans, dibenzothiofurans, acridines, benzoacridines, dibenzoacridines, and the like.

[0143] C n The subscript n in -heteroaryl simply refers to the number of carbon atoms excluding the number of heteroatoms. In this context, it is clear that a C heteroarylene group is an aromatic compound containing 3 carbon atoms, such as pyrazole, imidazole, oxazole, thiazole, etc.

[0144] The term "halogenated" refers to an organic compound in which one of its hydrogen atoms has been replaced by a halogen atom. The term "perhalogenated" refers to an organic compound in which all of its hydrogen atoms have been replaced by halogen atoms. The terms "fluorinated" and "perfluorinated" should be understood in the same way.

[0145] As used herein, the term "alkenyl" refers to the group -CR containing a carbon-carbon double bond. 1 =CR 2 R 3 Refers to... As used herein, the term "perhalogenated" refers to a hydrocarbyl group in which all of the hydrocarbyl group's hydrogen atoms have been replaced with halogen (F, Cl, Br, I) atoms.

[0146] As used herein, the term "alkoxy" refers to a structural fragment of the formula -OR, where R is hydrocarbyl, preferably alkyl or cycloalkyl.

[0147] As used herein, the term "thioalkyl" refers to a structural fragment of the formula -SR, where R is hydrocarbyl, preferably alkyl or cycloalkyl.

[0148] As used herein, the term single bond means a direct bond.

[0149] In the context of this invention, a group is "substituted" by another group if one of the hydrogen atoms contained in the group is replaced by another group, in which case the other group is the substituent.

[0150] In accordance with the present disclosure, in the following bonding scheme formula: [ka] The group A can be attached at any suitable bonding position. When the bond to A is shown to cross two or more rings, [ka] Group A can be attached at any suitable bonding position on each ring that crosses the bond.

[0151] In the context of the present invention, the term "between" with respect to a layer being between two other layers does not exclude the presence of an additional layer that may be disposed between the layer and one of the other two layers. In the context of the present invention, the term "in direct contact" with respect to two layers being in direct contact with each other means that no additional layer is disposed between the two layers. A layer deposited on another layer is considered to be in direct contact with this layer.

[0152] In the context of this specification, the terms "essentially non-emissive" or "non-emissive" mean that the contribution of a compound or layer to the visible emission spectrum from a device is less than 10%, preferably less than 5%, of the visible emission spectrum. The visible emission spectrum is the emission spectrum having wavelengths from about 380 nm to about 780 nm.

[0153] For the organic light emitting devices of the present invention, the compounds mentioned in the experimental section are considered to be most preferred.

[0154] Organic electroluminescent devices (OLEDs) can be bottom-emitting or top-emitting devices.

[0155] Another aspect is directed to a device comprising at least one organic electroluminescent device (OLED).Devices comprising organic light emitting diodes are, for example, displays and lighting panels.

[0156] For purposes of the present invention, the following defined terms shall have these definitions, unless a different definition is given in the claims or elsewhere in this specification.

[0157] In the context of this specification, the term "different" or "differs" in relation to matrix materials means that the matrix materials differ in their structural formula.

[0158] The energy levels of the highest occupied molecular orbital, also called the HOMO, and the lowest unoccupied molecular orbital, also called the LUMO, are measured in electron volts (eV).

[0159] The terms "OLED" and "organic light emitting diode" are used interchangeably and have the same meaning. As used herein, the term "organic electroluminescent device" can include both organic light emitting diodes as well as organic light emitting transistors (OLETs).

[0160] As used herein, "weight percent," "wt.-%," wt%, "percent by weight," "% by weight," and variations thereof refer to a composition, component, substance, or agent as the weight of that component, substance, or agent in each electron transport layer divided by the total weight of that respective electron transport layer multiplied by 100. It is understood that the total weight percent amount of all components, substances, and agents in each electron transport and electron injection layer is selected not to exceed 100 wt.-%.

[0161] As used herein, "volume percent," "vol.-%," "percent by volume," "% by volume," and variations thereof refer to a composition, component, substance, or agent as the volume of that component, substance, or agent in the respective electron transport layer divided by the total volume of that respective electron transport layer multiplied by 100. It is understood that the total volume percent amount of all components, substances, and agents in the cathode layer is selected not to exceed 100 vol.-%.

[0162] In this specification, all numerical values ​​are assumed to be modified by the term "about," whether explicitly stated or not. As used herein, the term "about" refers to possible variations in numerical quantities. Whether modified by the term "about," the claims include equivalents to the quantities.

[0163] It should be noted that as used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural references unless the content clearly dictates otherwise.

[0164] The terms "free of", "does not contain", and "does not comprise" do not exclude impurities. Impurities have no technical effect with respect to the objectives achieved by the present invention. The term "free of" a compound means that such compounds / materials are not intentionally added to the layer during processing.

[0165] Preferably, the semiconducting layer comprising a compound of formula (I) is essentially non-emissive or non-emissive.

[0166] The operating voltage (also called U) is 10 milliamperes per square centimeter (mA / cm 2 ) and is measured in volts (V).

[0167] Candela per ampere efficiency (also called cd / A efficiency) is measured in candela per ampere at 10 milliamperes per square centimeter (mA / cm2).

[0168] External quantum efficiency (also called EQE) is measured in percent (%).

[0169] The color space is described by the coordinates CIE-x and CIE-y (Commission Internationale de l'Eclairage 1931). For blue emission, CIE-y is particularly important: a smaller CIE-y indicates a deeper blue. Efficiency values ​​are compared at the same CIE-y.

[0170] The highest occupied molecular orbital, also called the HOMO, and the lowest unoccupied molecular orbital, also called the LUMO, are measured in electron volts (eV).

[0171] The terms "OLED," "organic light emitting diode," "organic light emitting device," "organic optoelectronic device," and "organic light emitting diode" are used interchangeably and have the same meaning.

[0172] "Lifespan" and "useful life" are used interchangeably and have the same meaning.

[0173] The anode and cathode may be expressed as an anode electrode / cathode electrode, or an anode electrode / cathode electrode, or an anode electrode layer / cathode electrode layer.

[0174] Room temperature, also known as ambient temperature, is 23 o It is C.

[0175] Hereinafter, the embodiments will be described in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Hereinafter, reference will be made in detail to exemplary embodiments.

[0176] DESCRIPTION OF THE DRAWINGS The aforementioned components, as well as the claimed components and components used in accordance with the present invention in the described embodiments, are not subject to any special exceptions with respect to their size, shape, material selection and technical concept, so that selection criteria known in the relevant art may be applied without limitation.

[0177]

[0013] Additional details, features, and advantages of the object of the present invention are disclosed in the dependent claims and the following description of the figures, which exemplarily show preferred embodiments according to the present invention. However, no embodiment necessarily represents the full scope of the invention, and therefore, reference is made to the claims and this specification to interpret the scope of the invention. It should be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the invention as claimed.

[0178] FIG. 1 is a schematic cross-sectional view of an organic semiconductor device according to an exemplary embodiment of the present invention; FIG. 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; FIG. 3 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0179] FIG. 4 is a schematic cross-sectional view of an OLED including a charge generating layer and two light-emitting layers according to an illustrative embodiment of the invention.

[0180] The figures are described in more detail below with reference to examples, although the present disclosure is not limited to the figures below.

[0181] Herein, when a first element is referred to as being formed or disposed "on" or "onto" a second element, the first element can be disposed directly on the second element, or one or more other elements can be disposed therebetween. When a first element is referred to as being formed or disposed "directly on" or "directly onto" a second element, no other elements are disposed therebetween.

[0182] 1 is a schematic cross-sectional view of an organic semiconductor device 100 according to an exemplary embodiment of the present invention. The organic semiconductor device 100 includes a substrate 110, an anode 120, an emissive layer (EML) 125, and a semiconductor layer 160 including or consisting of a semiconductor material according to the present invention. The semiconductor layer including or consisting of the semiconductor material 160 according to the present invention is formed on the EML 125. A cathode 190 is disposed on the organic semiconductor layer 160.

[0183] 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate 110, an anode 120, a hole-injection layer (HIL) 130, a hole-transport layer (HTL) 140, an emissive layer (EML) 150, and an electron-transport layer (ETL) 160. In this embodiment, the electron-transport layer is a semiconductor layer according to the present invention. The electron-transport layer (ETL) 160 is formed on the EML 150. An electron-injection layer (EIL) 180 is disposed on the electron-transport layer (ETL) 160. A cathode 190 is disposed directly on the electron-injection layer (EIL) 180.

[0184] Figure 3 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 3 differs from Figure 2 in that the OLED 100 of Figure 3 includes an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155.

[0185] Referring to FIG. 3 , the OLED 100 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emissive layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode electrode 190.

[0186] In this embodiment of FIG. 3, HBL 155 is a semiconducting layer comprising a compound of formula (I).

[0187] Figure 4 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 4 differs from Figure 3 in that the OLED 100 in Figure 4 further comprises a charge generation layer (CGL) and a second light-emitting layer (151).

[0188] Referring to FIG. 4 , OLED 100 includes a substrate 110, an anode 120, a first hole-injection layer (HIL) 130, a first hole-transport layer (HTL) 140, a first electron-blocking layer (EBL) 145, a first emissive layer (EML) 150, a first hole-blocking layer (HBL) 155, a first electron-transport layer (ETL) 160, an n-type charge-generating layer (n-type CGL) 185, a hole-generating layer (p-type charge-generating layer; p-type GCL) 135, a second hole-transporting layer (HTL) 141, a second electron-blocking layer (EBL) 146, a second emissive layer (EML) 151, a second hole-blocking layer (EBL) 156, a second electron-transporting layer (ETL) 161, a second electron-injection layer (EIL) 181, and a cathode 190.

[0189] In this embodiment of FIG. 4, HBL 155 is a semiconducting layer comprising the compound of formula (I).

[0190] 1, 2, 3, and 4, an encapsulating layer may be further formed on the cathode electrode 190 to encapsulate the OLED 100. In addition, various other modifications may be made.

[0191] Hereinafter, the embodiments will be described in more detail with reference to examples, but the present disclosure is not limited to the following examples.

[0192] [Synthesis Procedure] 4-phenyl-2-(2'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)quinazoline (E1) [ka] A three-neck round-bottom flask was flushed with nitrogen and charged with 2-(2-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-18-2, 1 eq, 11.9 g), 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline (CAS 1852465-26-9, 0.95 eq, 12.8 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.01 eq, 0.2 g), and potassium phosphate (CAS 7778-53-2, 2 eq, 12.4 g). A degassed mixture of 120 mL of dioxane and 30 mL of water was added. The reaction mixture was stirred overnight at 50°C under nitrogen atmosphere. Afterwards, the reaction mixture was cooled and the solvent was evaporated. The product was extracted with 250 mL of chloroform and washed with water. The combined organic phases were dried and filtered through a silica pad. The solvent was partially evaporated under reduced pressure and hexane was added. The white solid precipitate was filtered. Final purification was carried out by sublimation to give the product as a white crystalline solid. Yield: 11.5 g (67%); ESI-MS: 665

[0193] 4-phenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)quinazoline (E2) [ka] A three-necked round-bottom flask was flushed with nitrogen and charged with 2-(3-chlorophenyl)-4-phenylquinazoline (CAS 540466-41-9, 1 eq, 25.0 g), 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine (CAS 2396743-64-7, 1.1 eq, 44.3 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.01 eq, 0.5 g), and potassium phosphate (CAS 7778-53-2, 2 eq, 33.5 g). A degassed mixture of 440 mL of dioxane and 80 mL of water was added. The reaction mixture was stirred overnight at 45°C under nitrogen atmosphere. After cooling to room temperature, a brown suspension formed. The crude solid was filtered and washed with dioxane and water. The product was dissolved hot in 1.1 L of toluene and filtered hot through a silica pad. The first fraction of the filtrate was discarded and the pad was further eluted with excess dichloromethane. The solvent was then evaporated and the crude product was refluxed in 300 mL of methyl tert-butyl ether and filtered. Final purification was achieved by sublimation, and the product was obtained as a white powder. Yield: 26.4 g (52%); ESI-MS: 665

[0194] 4,6-Diphenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)pyrimidine (E3) [ka] A three-necked round-bottom flask was flushed with nitrogen and charged with 2-(3-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-17-1) (1 eq, 18.9 g), 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (CAS 1381862-91-4) (1 eq, 20.1 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3) (0.2 eq, 1.0 g), and potassium carbonate (CAS 584-08-7) (3 eq, 18.0 g). A degassed mixture of 260 mL of dioxane and 65 mL of water was added. The reaction mixture was stirred overnight at 70 °C under a nitrogen atmosphere. After cooling to room temperature, a dark gray suspension was formed. The raw solid was filtered and washed with dioxane, water, and methanol. The product was then extracted with toluene in a Soxhlet apparatus. After the extract was cooled, a white precipitate formed, which was filtered and washed with hexane. The product was then washed with 300 mL of hot toluene. Final purification was performed by sublimation, and the product was obtained as a white powder. Yield: 23.9 g (79%); ESI-MS: 691

[0195] 4,6-Diphenyl-2-(4'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)pyrimidine (E4) [ka] A three-necked round-bottom flask was flushed with nitrogen and charged with 2-(4-bromophenyl)-3,5,6-triphenylpyrazine (CAS 943442-81-7) (1 eq, 18.9 g), 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (CAS 1381862-91-4) (1 eq, 20.1 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3) (0.02 eq, 1.0 g), and potassium carbonate (CAS 584-08-7) (3 eq, 18.0 g). A degassed mixture of 260 mL of dioxane and 65 mL of water was added. The reaction mixture was stirred overnight at 70 °C under a nitrogen atmosphere. After cooling to room temperature, a gray suspension was formed. The raw solid was filtered and washed with dioxane and water. The product was then extracted with toluene in a Soxhlet apparatus. Upon cooling, a white precipitate formed. The solid was filtered and washed with hexane. Final purification was achieved by sublimation, and the product was obtained as a white powder. Yield: 23.9 g (79%); ESI-MS: 691

[0196] 4,6-Diphenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-4-yl)pyrimidine (E5) [ka] A three-necked round-bottom flask was flushed with nitrogen and charged with 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (CAS 1613163-88-4, 1 eq, 25.0 g), 2-(3-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-17-1, 1 eq, 23.4 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3, 0.02 eq, 1.3 g), and potassium carbonate (CAS 584-08-7, 2 eq, 14.9 g). A degassed mixture of 480 mL of THF and 60 mL of water was added. The reaction mixture was stirred overnight at 75 °C under a nitrogen atmosphere. After cooling to room temperature, a yellow suspension was formed. The raw solid was filtered and washed with THF and water. The product was then dissolved in 800 mL of chloroform and filtered through a silica pad. The resulting solution was partially evaporated and a mixture of 5% methanol in hexane was added. A white precipitate formed and the solid was filtered. Final purification was performed by sublimation and the product was obtained as a white powder. Yield: 18.9 g (51%), ESI-MS: 691

[0197] 4-phenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)benzo[h]quinazoline (E6) [ka] A three-necked round-bottom flask was flushed with nitrogen and charged with 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[h]quinazoline (CAS 2639481-16-4, 1 eq, 20.0 g), 2-(3-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-17-1, 1 eq, 20.2 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3, 0.02 eq, 1.0 g), and potassium carbonate (CAS 584-08-7, 3 eq, 12.1 g). A degassed mixture of 200 mL of dioxane and 50 mL of water was added. The reaction mixture was stirred overnight at 75 °C under a nitrogen atmosphere. After cooling to room temperature, a dark gray suspension was formed. The raw solid was filtered and washed with dioxane, water, and methanol. The product was then extracted with chlorobenzene in a Soxhlet apparatus. After the extract was cooled, a white precipitate formed, which was filtered and washed with hexane. The solid was washed with 400 mL of hot THF and filtered. The product was recrystallized from chlorobenzene. Final purification was performed by sublimation, and the product was obtained as a white powder. Yield: 18.4 g (59%). ESI-MS: 715

[0198] 4-Phenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-2-yl)quinazoline (E7) [ka] A three-necked round-bottom flask was flushed with nitrogen and charged with 2-(2-chlorophenyl)-4-phenylquinazoline (CAS 1283751-33-6, 1 eq, 12.8 g), 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine (CAS 2396743-64-7, 1.05 eq, 21.7 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.03 eq, 7.3 g), potassium phosphate (CAS 7778-53-2, 2 eq, 17.2 g), and a degassed mixture of 300 mL of dioxane and 100 mL of water. The reaction mixture was stirred overnight at 90°C under nitrogen atmosphere. After cooling to room temperature, a grey suspension was formed. The raw solid was filtered and washed with dioxane, water, and methanol. The product was then dissolved in dichloromethane and filtered through a silica pad. The resulting solution was partially evaporated and methanol was added. A white precipitate formed and was filtered. Final purification was performed by sublimation, and the product was obtained as a white powder. Yield: 15.4g (57%). ESI-MS: 665

[0199] Auxiliary materials for device experiments F1 is: [ka]

[0200] F2 is: [ka]

[0201] F3 is: [ka]

[0202] F4 is: [ka]

[0203] PD2 is: [ka]

[0204] LiQ is lithium 8-hydroxyquinolinoleate, CAS 850918-68-2.

[0205] BH1 is: [ka]

[0206] BD1 is: [ka]

[0207] ITO is indium tin oxide.

[0208] [Comparative Compounds] [ka]

[0209] [Organic EL Device] Blue fluorescent top-emission OLED Table 1a shows a schematic of the model device used for the described OLED tests.

[0210] [Table 1]

[0211] The results are shown in Tables 2 to 5.

[0212] [Table 2]

[0213] Compared to the state of the art compound C1, the compounds of the present invention allow for longer lifetimes and higher current efficiencies.

[0214] [Table 3]

[0215] Compared to the state of the art, represented by compound C2, the compounds of the present invention allow for longer lifetimes and higher current efficiencies.

[0216] [Table 4]

[0217] Compared to the state of the art, represented by compound C3, the compounds of the present invention allow for longer lifetimes and higher current efficiencies.

[0218] [Table 5]

[0219] Compared to the state of the art represented by compound C4, compound E6 of the present invention allows for a longer lifetime and higher current efficiency.

[0220] The features disclosed in the foregoing description and in the dependent claims may, both separately and in any combination thereof, be material for realising aspects of the disclosure as defined in the independent claims in diverse forms. [Brief explanation of the drawings]

[0221] [Figure 1] 1 is a schematic cross-sectional view of an organic semiconductor device according to an exemplary embodiment of the present invention. [Figure 2] 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED), according to an exemplary embodiment of the present invention. [Figure 3]1 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention. [Figure 4] 1 is a schematic cross-sectional view of an OLED including a charge generating layer and two light-emitting layers according to an exemplary embodiment of the present invention.

Claims

1. A compound of formula (I) 【Chemistry 1】 where -A, A' and A'' are substituted or unsubstituted C １ ~C ２０ Alkyl, substituted or unsubstituted C １ ~C ２０ Alkenyl, substituted or unsubstituted C ６ ~C ６０ Aryl, and substituted or unsubstituted C ２ ~C ６０ independently selected from the group consisting of heteroaryl; -L and L'' are substituted or unsubstituted C ６ ~C ６０ Aryl and substituted or unsubstituted C ２ ~C ６０ heteroaryl; L' is independently selected from the group consisting of H, D, C １ ~C ２０ Alkyl, substituted or unsubstituted C １ ~C ２０ Alkenyl, substituted or unsubstituted C ６ ~C ６０ Aryl, and substituted or unsubstituted C ２ ~C ６０ selected from the group consisting of heteroaryl; or -L is a substituted or unsubstituted C ６ ~C ６０ Aryl and substituted or unsubstituted C ２ ~C ６０ heteroaryl, wherein L′ and L″ together form a fused 6-membered aromatic ring; wherein the fused 6-membered aromatic ring is - unsubstituted or or -C ６ ~C ５６ substituted with one or more substituents independently selected from aryl, provided that the total number of C atoms of all the substituents does not exceed 56; or - fused to a second 6-membered aromatic ring, wherein said fused 6-membered aromatic ring and said second 6-membered aromatic ring are unsubstituted or at least one of said fused 6-membered aromatic ring and said second 6-membered aromatic ring is C ６ ~C ４０ a fused 6-membered aromatic ring substituted with one or more substituents independently selected from aryl, with the proviso that the total number of C atoms of all the substituents does not exceed 40; -E is H, D, D, halogen, SiR ａ R ｂ R ｃ (Here, R ａ , R ｂ and R ｃ is C １ ~C ６ independently selected from the group consisting of alkyl and phenyl), C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, CN and P(=O)R ｄ R ｅ (Here, R ｄ and R ｅ is C １ ~C ６ independently selected from the group consisting of alkyl and phenyl; -G is H, D, halogen, SiR ａ R ｂ R ｃ (Here, R ａ , R ｂ and R ｃ is C １ ~C ６ independently selected from the group consisting of alkyl and phenyl), C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, CN and P(=O)R ｄ R ｅ (Here, R ｄ and R ｅ is C １ ~C ６ and phenyl).

2. A, A' and A'' are C ６ ~C ６０ 2. The compound of claim 1, wherein each of the following is independently selected from aryl:

3. 3. The compound of claim 1 or 2, wherein A, A', and A'' are each phenyl.

4. L and L″ are substituted or unsubstituted C ６ ~C ６０ aryl, and L' is H; or -L is substituted or unsubstituted C ６ ~C ６０ aryl, and L′ and L″ together form a fused 6-membered aromatic ring; wherein the fused 6-membered aromatic ring is - unsubstituted or or - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted.

5. L and L″ are each phenyl and L′ is H; or The compound according to any one of claims 1 to 4, wherein L is phenyl and L' and L'' together form an unsubstituted fused 6-membered aromatic ring.

6. The compound of any one of claims 1 to 5, wherein E is H.

7. The compound of any one of claims 1 to 6, wherein G is H.

8. A semiconductor material comprising a compound of formula (I) according to any one of claims 1 to 7.

9. 10. An organic electronic device comprising a semiconducting layer, characterized in that the semiconducting layer comprises the semiconducting material of claim 8.

10. 10. The organic electronic device of claim 9, wherein the semiconducting layer is a hole-blocking layer and / or an electron-transporting layer and / or an electron-injecting layer.

11. 11. An organic electronic device according to claim 9 or 10, wherein the semiconducting layer is a hole-blocking layer.

12. 12. The organic electronic device of claim 11, further comprising an emissive layer and an electron transport layer, wherein the hole blocking layer is disposed between the emissive layer and the electron transport layer.

13. 13. The organic electronic device of claim 12, which is an organic light-emitting diode.

14. A display device comprising the organic electronic device of claim 13.

15. A process for preparing an organic electronic device according to claim 12 or 13, comprising the step of depositing a compound according to any one of claims 1 to 8 on a solid support.

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